feat(coderd/database): add automations database schema and queries

Adds the database layer for the chat automations feature:

Schema (migration 000454):
- chat_automations table with status, rate limits, instructions, MCP config
- chat_automation_triggers table (webhook + cron types)
- chat_automation_events table for audit trail
- Indexes for performance and unique constraint on (owner, org, name)
- automation_id FK on chats table

SQL queries:
- chatautomations.sql: CRUD with authorize_filter support
- chatautomationtriggers.sql: CRUD + GetActiveChatAutomationCronTriggers JOIN query
- chatautomationevents.sql: insert, list, count windows, purge

RBAC:
- chat_automation resource with CRUD actions
- dbauthz wrappers for all 18 query methods

Also adds LockIDChatAutomationCron advisory lock constant.

.github/actions/setup-go/action.yaml

@@ -4,7 +4,7 @@ description: |
 inputs:
   version:
     description: "The Go version to use."
-    default: "1.25.7"
+    default: "1.25.8"
   use-cache:
     description: "Whether to use the cache."
     default: "true"

.github/workflows/doc-check.yaml

@@ -240,6 +240,7 @@ jobs:
       - name: Create Coder Task for Documentation Check
         if: steps.check-secrets.outputs.skip != 'true'
         id: create_task
+        continue-on-error: true
         uses: ./.github/actions/create-task-action
         with:
           coder-url: ${{ secrets.DOC_CHECK_CODER_URL }}
@@ -254,8 +255,21 @@ jobs:
           github-issue-url: ${{ steps.determine-context.outputs.pr_url }}
           comment-on-issue: false
 
+      - name: Handle Task Creation Failure
+        if: steps.check-secrets.outputs.skip != 'true' && steps.create_task.outcome != 'success'
+        run: |
+          {
+            echo "## Documentation Check Task"
+            echo ""
+            echo "⚠️ The external Coder task service was unavailable, so this"
+            echo "advisory documentation check did not run."
+            echo ""
+            echo "Maintainers can rerun the workflow or trigger it manually"
+            echo "after the service recovers."
+          } >> "${GITHUB_STEP_SUMMARY}"
+
       - name: Write Task Info
-        if: steps.check-secrets.outputs.skip != 'true'
+        if: steps.check-secrets.outputs.skip != 'true' && steps.create_task.outcome == 'success'
         env:
           TASK_CREATED: ${{ steps.create_task.outputs.task-created }}
           TASK_NAME: ${{ steps.create_task.outputs.task-name }}
@@ -273,7 +287,7 @@ jobs:
           } >> "${GITHUB_STEP_SUMMARY}"
 
       - name: Wait for Task Completion
-        if: steps.check-secrets.outputs.skip != 'true'
+        if: steps.check-secrets.outputs.skip != 'true' && steps.create_task.outcome == 'success'
         id: wait_task
         env:
           TASK_NAME: ${{ steps.create_task.outputs.task-name }}
@@ -363,7 +377,7 @@ jobs:
           fi
 
       - name: Fetch Task Logs
-        if: always() && steps.check-secrets.outputs.skip != 'true'
+        if: always() && steps.check-secrets.outputs.skip != 'true' && steps.create_task.outcome == 'success'
         env:
           TASK_NAME: ${{ steps.create_task.outputs.task-name }}
         run: |
@@ -376,7 +390,7 @@ jobs:
           echo "::endgroup::"
 
       - name: Cleanup Task
-        if: always() && steps.check-secrets.outputs.skip != 'true'
+        if: always() && steps.check-secrets.outputs.skip != 'true' && steps.create_task.outcome == 'success'
         env:
           TASK_NAME: ${{ steps.create_task.outputs.task-name }}
         run: |
@@ -390,6 +404,7 @@ jobs:
       - name: Write Final Summary
         if: always() && steps.check-secrets.outputs.skip != 'true'
         env:
+          CREATE_TASK_OUTCOME: ${{ steps.create_task.outcome }}
           TASK_NAME: ${{ steps.create_task.outputs.task-name }}
           TASK_MESSAGE: ${{ steps.wait_task.outputs.task_message }}
           RESULT_URI: ${{ steps.wait_task.outputs.result_uri }}
@@ -400,10 +415,15 @@ jobs:
             echo "---"
             echo "### Result"
             echo ""
-            echo "**Status:** ${TASK_MESSAGE:-Task completed}"
-            if [[ -n "${RESULT_URI}" ]]; then
-              echo "**Comment:** ${RESULT_URI}"
+            if [[ "${CREATE_TASK_OUTCOME}" == "success" ]]; then
+              echo "**Status:** ${TASK_MESSAGE:-Task completed}"
+              if [[ -n "${RESULT_URI}" ]]; then
+                echo "**Comment:** ${RESULT_URI}"
+              fi
+              echo ""
+              echo "Task \`${TASK_NAME}\` has been cleaned up."
+            else
+              echo "**Status:** Skipped because the external Coder task"
+              echo "service was unavailable."
             fi
-            echo ""
-            echo "Task \`${TASK_NAME}\` has been cleaned up."
           } >> "${GITHUB_STEP_SUMMARY}"

.github/workflows/weekly-docs.yaml

@@ -46,6 +46,12 @@ jobs:
             echo "    replacement: \"https://github.com/coder/coder/tree/${HEAD_SHA}/\""
           } >> .github/.linkspector.yml
 
+      # TODO: Remove this workaround once action-linkspector sets
+      # package-manager-cache: false in its internal setup-node step.
+      # See: https://github.com/UmbrellaDocs/action-linkspector/issues/54
+      - name: Enable corepack
+        run: corepack enable pnpm
+
       - name: Check Markdown links
         uses: umbrelladocs/action-linkspector@37c85bcde51b30bf929936502bac6bfb7e8f0a4d # v1.4.1
         id: markdown-link-check

agent/agentssh/x11_test.go

@@ -211,7 +211,7 @@ func TestServer_X11_EvictionLRU(t *testing.T) {
 		require.NoError(t, err)
 		stderr, err := sess.StderrPipe()
 		require.NoError(t, err)
-		require.NoError(t, sess.Shell())
+		require.NoError(t, sess.Start("sh"))
 
 		// The SSH server lazily starts the session. We need to write a command
 		// and read back to ensure the X11 forwarding is started.

cli/schedule_test.go

@@ -352,8 +352,6 @@ func TestScheduleOverride(t *testing.T) {
 			require.NoError(t, err, "invalid schedule")
 			ownerClient, _, _, ws := setupTestSchedule(t, sched)
 			now := time.Now()
-			// To avoid the likelihood of time-related flakes, only matching up to the hour.
-			expectedDeadline := now.In(loc).Add(10 * time.Hour).Format("2006-01-02T15:")
 
 			// When: we override the stop schedule
 			inv, root := clitest.New(t,
@@ -364,6 +362,19 @@ func TestScheduleOverride(t *testing.T) {
 			pty := ptytest.New(t).Attach(inv)
 			require.NoError(t, inv.Run())
 
+			// Fetch the workspace to get the actual deadline set by the
+			// server. Computing our own expected deadline from a separately
+			// captured time.Now() is racy: the CLI command calls time.Now()
+			// internally, and with the Asia/Kolkata +05:30 offset the hour
+			// boundary falls at :30 UTC minutes. A small delay between our
+			// time.Now() and the command's is enough to land in different
+			// hours.
+			updated, err := ownerClient.Workspace(context.Background(), ws[0].ID)
+			require.NoError(t, err)
+			require.False(t, updated.LatestBuild.Deadline.IsZero(), "deadline should be set after extend")
+			require.WithinDuration(t, now.Add(10*time.Hour), updated.LatestBuild.Deadline.Time, 5*time.Minute)
+			expectedDeadline := updated.LatestBuild.Deadline.Time.In(loc).Format(time.RFC3339)
+
 			// Then: the updated schedule should be shown
 			pty.ExpectMatch(ws[0].OwnerName + "/" + ws[0].Name)
 			pty.ExpectMatch(sched.Humanize())

cli/testdata/server-config.yaml.golden

@@ -857,13 +857,18 @@ aibridgeproxy:
   # Comma-separated list of AI provider domains for which HTTPS traffic will be
   # decrypted and routed through AI Bridge. Requests to other domains will be
   # tunneled directly without decryption. Supported domains: api.anthropic.com,
-  # api.openai.com, api.individual.githubcopilot.com.
-  # (default: api.anthropic.com,api.openai.com,api.individual.githubcopilot.com,
+  # api.openai.com, api.individual.githubcopilot.com,
+  # api.business.githubcopilot.com, api.enterprise.githubcopilot.com, chatgpt.com.
+  # (default:
+  # api.anthropic.com,api.openai.com,api.individual.githubcopilot.com,api.business.githubcopilot.com,api.enterprise.githubcopilot.com,chatgpt.com,
   # type: string-array)
   domain_allowlist:
     - api.anthropic.com
     - api.openai.com
     - api.individual.githubcopilot.com
+    - api.business.githubcopilot.com
+    - api.enterprise.githubcopilot.com
+    - chatgpt.com
   # URL of an upstream HTTP proxy to chain tunneled (non-allowlisted) requests
   # through. Format: http://[user:pass@]host:port or https://[user:pass@]host:port.
   # (default: <unset>, type: string)

coderd/aibridge/aibridge.go

@@ -20,6 +20,21 @@ const HeaderCoderToken = "X-Coder-AI-Governance-Token" //nolint:gosec // This is
 // request forwarded to aibridged for cross-service log correlation.
 const HeaderCoderRequestID = "X-Coder-AI-Governance-Request-Id"
 
+// Copilot provider.
+const (
+	ProviderCopilotBusiness   = "copilot-business"
+	HostCopilotBusiness       = "api.business.githubcopilot.com"
+	ProviderCopilotEnterprise = "copilot-enterprise"
+	HostCopilotEnterprise     = "api.enterprise.githubcopilot.com"
+)
+
+// ChatGPT provider.
+const (
+	ProviderChatGPT = "chatgpt"
+	HostChatGPT     = "chatgpt.com"
+	BaseURLChatGPT  = "https://" + HostChatGPT + "/backend-api/codex"
+)
+
 // IsBYOK reports whether the request is using BYOK mode, determined
 // by the presence of the X-Coder-AI-Governance-Token header.
 func IsBYOK(header http.Header) bool {

coderd/apidoc/docs.go

@@ -13445,6 +13445,11 @@ const docTemplate = `{
                 "chat:delete",
                 "chat:read",
                 "chat:update",
+                "chat_automation:*",
+                "chat_automation:create",
+                "chat_automation:delete",
+                "chat_automation:read",
+                "chat_automation:update",
                 "coder:all",
                 "coder:apikeys.manage_self",
                 "coder:application_connect",
@@ -13654,6 +13659,11 @@ const docTemplate = `{
                 "APIKeyScopeChatDelete",
                 "APIKeyScopeChatRead",
                 "APIKeyScopeChatUpdate",
+                "APIKeyScopeChatAutomationAll",
+                "APIKeyScopeChatAutomationCreate",
+                "APIKeyScopeChatAutomationDelete",
+                "APIKeyScopeChatAutomationRead",
+                "APIKeyScopeChatAutomationUpdate",
                 "APIKeyScopeCoderAll",
                 "APIKeyScopeCoderApikeysManageSelf",
                 "APIKeyScopeCoderApplicationConnect",
@@ -19038,6 +19048,7 @@ const docTemplate = `{
                 "audit_log",
                 "boundary_usage",
                 "chat",
+                "chat_automation",
                 "connection_log",
                 "crypto_key",
                 "debug_info",
@@ -19084,6 +19095,7 @@ const docTemplate = `{
                 "ResourceAuditLog",
                 "ResourceBoundaryUsage",
                 "ResourceChat",
+                "ResourceChatAutomation",
                 "ResourceConnectionLog",
                 "ResourceCryptoKey",
                 "ResourceDebugInfo",

coderd/apidoc/swagger.json

@@ -12015,6 +12015,11 @@
 				"chat:delete",
 				"chat:read",
 				"chat:update",
+				"chat_automation:*",
+				"chat_automation:create",
+				"chat_automation:delete",
+				"chat_automation:read",
+				"chat_automation:update",
 				"coder:all",
 				"coder:apikeys.manage_self",
 				"coder:application_connect",
@@ -12224,6 +12229,11 @@
 				"APIKeyScopeChatDelete",
 				"APIKeyScopeChatRead",
 				"APIKeyScopeChatUpdate",
+				"APIKeyScopeChatAutomationAll",
+				"APIKeyScopeChatAutomationCreate",
+				"APIKeyScopeChatAutomationDelete",
+				"APIKeyScopeChatAutomationRead",
+				"APIKeyScopeChatAutomationUpdate",
 				"APIKeyScopeCoderAll",
 				"APIKeyScopeCoderApikeysManageSelf",
 				"APIKeyScopeCoderApplicationConnect",
@@ -17410,6 +17420,7 @@
 				"audit_log",
 				"boundary_usage",
 				"chat",
+				"chat_automation",
 				"connection_log",
 				"crypto_key",
 				"debug_info",
@@ -17456,6 +17467,7 @@
 				"ResourceAuditLog",
 				"ResourceBoundaryUsage",
 				"ResourceChat",
+				"ResourceChatAutomation",
 				"ResourceConnectionLog",
 				"ResourceCryptoKey",
 				"ResourceDebugInfo",

coderd/authorize.go

@@ -220,7 +220,7 @@ func (api *API) checkAuthorization(rw http.ResponseWriter, r *http.Request) {
 			Type:        string(v.Object.ResourceType),
 			AnyOrgOwner: v.Object.AnyOrgOwner,
 		}
-		if obj.Owner == "me" {
+		if obj.Owner == codersdk.Me {
 			obj.Owner = auth.ID
 		}
 

coderd/database/check_constraint.go

@@ -7,6 +7,11 @@ type CheckConstraint string
 // CheckConstraint enums.
 const (
 	CheckAPIKeysAllowListNotEmpty                    CheckConstraint = "api_keys_allow_list_not_empty"                      // api_keys
+	CheckChatAutomationEventsChatExclusivity         CheckConstraint = "chat_automation_events_chat_exclusivity"            // chat_automation_events
+	CheckChatAutomationTriggersCronFields            CheckConstraint = "chat_automation_triggers_cron_fields"               // chat_automation_triggers
+	CheckChatAutomationTriggersWebhookFields         CheckConstraint = "chat_automation_triggers_webhook_fields"            // chat_automation_triggers
+	CheckChatAutomationsMaxChatCreatesPerHourCheck   CheckConstraint = "chat_automations_max_chat_creates_per_hour_check"   // chat_automations
+	CheckChatAutomationsMaxMessagesPerHourCheck      CheckConstraint = "chat_automations_max_messages_per_hour_check"       // chat_automations
 	CheckChatModelConfigsCompressionThresholdCheck   CheckConstraint = "chat_model_configs_compression_threshold_check"     // chat_model_configs
 	CheckChatModelConfigsContextLimitCheck           CheckConstraint = "chat_model_configs_context_limit_check"             // chat_model_configs
 	CheckChatProvidersProviderCheck                  CheckConstraint = "chat_providers_provider_check"                      // chat_providers

coderd/database/db2sdk/db2sdk.go

@@ -1572,6 +1572,17 @@ func Chat(c database.Chat, diffStatus *database.ChatDiffStatus) codersdk.Chat {
 		convertedDiffStatus := ChatDiffStatus(c.ID, diffStatus)
 		chat.DiffStatus = &convertedDiffStatus
 	}
+	if c.LastInjectedContext.Valid {
+		var parts []codersdk.ChatMessagePart
+		// Internal fields are stripped at write time in
+		// chatd.updateLastInjectedContext, so no
+		// StripInternal call is needed here. Unmarshal
+		// errors are suppressed — the column is written by
+		// us with a known schema.
+		if err := json.Unmarshal(c.LastInjectedContext.RawMessage, &parts); err == nil {
+			chat.LastInjectedContext = parts
+		}
+	}
 	return chat
 }
 

coderd/database/db2sdk/db2sdk_test.go

@@ -541,6 +541,13 @@ func TestChat_AllFieldsPopulated(t *testing.T) {
 		PinOrder:          1,
 		MCPServerIDs:      []uuid.UUID{uuid.New()},
 		Labels:            database.StringMap{"env": "prod"},
+		LastInjectedContext: pqtype.NullRawMessage{
+			// Use a context-file part to verify internal
+			// fields are not present (they are stripped at
+			// write time by chatd, not at read time).
+			RawMessage: json.RawMessage(`[{"type":"context-file","context_file_path":"/AGENTS.md"}]`),
+			Valid:      true,
+		},
 	}
 	// Only ChatID is needed here. This test checks that
 	// Chat.DiffStatus is non-nil, not that every DiffStatus

coderd/database/dbauthz/dbauthz.go

@@ -1570,13 +1570,13 @@ func (q *querier) AllUserIDs(ctx context.Context, includeSystem bool) ([]uuid.UU
 	return q.db.AllUserIDs(ctx, includeSystem)
 }
 
-func (q *querier) ArchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (q *querier) ArchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	chat, err := q.db.GetChatByID(ctx, id)
 	if err != nil {
-		return err
+		return nil, err
 	}
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
-		return err
+		return nil, err
 	}
 	return q.db.ArchiveChatByID(ctx, id)
 }
@@ -1694,6 +1694,13 @@ func (q *querier) CleanTailnetTunnels(ctx context.Context) error {
 	return q.db.CleanTailnetTunnels(ctx)
 }
 
+func (q *querier) CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error {
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChatAutomation); err != nil {
+		return err
+	}
+	return q.db.CleanupDeletedMCPServerIDsFromChatAutomations(ctx)
+}
+
 func (q *querier) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceChat); err != nil {
 		return err
@@ -1731,6 +1738,28 @@ func (q *querier) CountAuditLogs(ctx context.Context, arg database.CountAuditLog
 	return q.db.CountAuthorizedAuditLogs(ctx, arg, prep)
 }
 
+func (q *querier) CountChatAutomationChatCreatesInWindow(ctx context.Context, arg database.CountChatAutomationChatCreatesInWindowParams) (int64, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
+		return 0, err
+	}
+	return q.db.CountChatAutomationChatCreatesInWindow(ctx, arg)
+}
+
+func (q *querier) CountChatAutomationMessagesInWindow(ctx context.Context, arg database.CountChatAutomationMessagesInWindowParams) (int64, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+	if err != nil {
+		return 0, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
+		return 0, err
+	}
+	return q.db.CountChatAutomationMessagesInWindow(ctx, arg)
+}
+
 func (q *querier) CountConnectionLogs(ctx context.Context, arg database.CountConnectionLogsParams) (int64, error) {
 	// Just like the actual query, shortcut if the user is an owner.
 	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceConnectionLog)
@@ -1842,6 +1871,28 @@ func (q *querier) DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, u
 	return q.db.DeleteApplicationConnectAPIKeysByUserID(ctx, userID)
 }
 
+func (q *querier) DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error {
+	return deleteQ(q.log, q.auth, q.db.GetChatAutomationByID, q.db.DeleteChatAutomationByID)(ctx, id)
+}
+
+// Triggers are sub-resources of an automation. Deleting a trigger
+// is a configuration change, so we authorize ActionUpdate on the
+// parent rather than ActionDelete.
+func (q *querier) DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error {
+	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, id)
+	if err != nil {
+		return err
+	}
+	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return err
+	}
+	return q.db.DeleteChatAutomationTriggerByID(ctx, id)
+}
+
 func (q *querier) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceDeploymentConfig); err != nil {
 		return err
@@ -2386,6 +2437,16 @@ func (q *querier) GetActiveAISeatCount(ctx context.Context) (int64, error) {
 	return q.db.GetActiveAISeatCount(ctx)
 }
 
+// GetActiveChatAutomationCronTriggers is a system-level query used by
+// the cron scheduler. It requires read permission on all automations
+// (admin gate) because it fetches triggers across all orgs and owners.
+func (q *querier) GetActiveChatAutomationCronTriggers(ctx context.Context) ([]database.GetActiveChatAutomationCronTriggersRow, error) {
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChatAutomation.All()); err != nil {
+		return nil, err
+	}
+	return q.db.GetActiveChatAutomationCronTriggers(ctx)
+}
+
 func (q *querier) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceTemplate.All()); err != nil {
 		return nil, err
@@ -2477,6 +2538,64 @@ func (q *querier) GetAuthorizationUserRoles(ctx context.Context, userID uuid.UUI
 	return q.db.GetAuthorizationUserRoles(ctx, userID)
 }
 
+func (q *querier) GetChatAutomationByID(ctx context.Context, id uuid.UUID) (database.ChatAutomation, error) {
+	return fetch(q.log, q.auth, q.db.GetChatAutomationByID)(ctx, id)
+}
+
+func (q *querier) GetChatAutomationEventsByAutomationID(ctx context.Context, arg database.GetChatAutomationEventsByAutomationIDParams) ([]database.ChatAutomationEvent, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+	if err != nil {
+		return nil, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatAutomationEventsByAutomationID(ctx, arg)
+}
+
+func (q *querier) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
+	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, id)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return trigger, nil
+}
+
+func (q *querier) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, automationID)
+	if err != nil {
+		return nil, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, automation); err != nil {
+		return nil, err
+	}
+	return q.db.GetChatAutomationTriggersByAutomationID(ctx, automationID)
+}
+
+func (q *querier) GetChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams) ([]database.ChatAutomation, error) {
+	// Shortcut if the caller has broad read access (e.g. site admins
+	// / owners). The SQL filter is noticeable, so skip it when we
+	// can.
+	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChatAutomation.All())
+	if err == nil {
+		return q.db.GetChatAutomations(ctx, arg)
+	}
+
+	// Fall back to SQL-level row filtering for normal users.
+	prep, err := prepareSQLFilter(ctx, q.auth, policy.ActionRead, rbac.ResourceChatAutomation.Type)
+	if err != nil {
+		return nil, xerrors.Errorf("prepare chat automation SQL filter: %w", err)
+	}
+	return q.db.GetAuthorizedChatAutomations(ctx, arg, prep)
+}
+
 func (q *querier) GetChatByID(ctx context.Context, id uuid.UUID) (database.Chat, error) {
 	return fetch(q.log, q.auth, q.db.GetChatByID)(ctx, id)
 }
@@ -2811,7 +2930,15 @@ func (q *querier) GetDERPMeshKey(ctx context.Context) (string, error) {
 }
 
 func (q *querier) GetDefaultChatModelConfig(ctx context.Context) (database.ChatModelConfig, error) {
-	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceDeploymentConfig); err != nil {
+	// Any user who can read chat resources can read the default
+	// model config, since model resolution is required to create
+	// a chat. This avoids gating on ResourceDeploymentConfig
+	// which regular members lack.
+	act, ok := ActorFromContext(ctx)
+	if !ok {
+		return database.ChatModelConfig{}, ErrNoActor
+	}
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceChat.WithOwner(act.ID)); err != nil {
 		return database.ChatModelConfig{}, err
 	}
 	return q.db.GetDefaultChatModelConfig(ctx)
@@ -4764,6 +4891,36 @@ func (q *querier) InsertChat(ctx context.Context, arg database.InsertChatParams)
 	return insert(q.log, q.auth, rbac.ResourceChat.WithOwner(arg.OwnerID.String()), q.db.InsertChat)(ctx, arg)
 }
 
+func (q *querier) InsertChatAutomation(ctx context.Context, arg database.InsertChatAutomationParams) (database.ChatAutomation, error) {
+	return insert(q.log, q.auth, rbac.ResourceChatAutomation.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), q.db.InsertChatAutomation)(ctx, arg)
+}
+
+// Events are append-only records produced by the system when
+// triggers fire. We authorize ActionUpdate on the parent
+// automation because inserting an event is a side-effect of
+// processing the automation, not an independent create action.
+func (q *querier) InsertChatAutomationEvent(ctx context.Context, arg database.InsertChatAutomationEventParams) (database.ChatAutomationEvent, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+	if err != nil {
+		return database.ChatAutomationEvent{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return database.ChatAutomationEvent{}, err
+	}
+	return q.db.InsertChatAutomationEvent(ctx, arg)
+}
+
+func (q *querier) InsertChatAutomationTrigger(ctx context.Context, arg database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	automation, err := q.db.GetChatAutomationByID(ctx, arg.AutomationID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return q.db.InsertChatAutomationTrigger(ctx, arg)
+}
+
 func (q *querier) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	// Authorize create on chat resource scoped to the owner and org.
 	return insert(q.log, q.auth, rbac.ResourceChat.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), q.db.InsertChatFile)(ctx, arg)
@@ -5561,6 +5718,13 @@ func (q *querier) PopNextQueuedMessage(ctx context.Context, chatID uuid.UUID) (d
 	return q.db.PopNextQueuedMessage(ctx, chatID)
 }
 
+func (q *querier) PurgeOldChatAutomationEvents(ctx context.Context, arg database.PurgeOldChatAutomationEventsParams) (int64, error) {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceChatAutomation.All()); err != nil {
+		return 0, err
+	}
+	return q.db.PurgeOldChatAutomationEvents(ctx, arg)
+}
+
 func (q *querier) ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error {
 	template, err := q.db.GetTemplateByID(ctx, templateID)
 	if err != nil {
@@ -5641,13 +5805,13 @@ func (q *querier) TryAcquireLock(ctx context.Context, id int64) (bool, error) {
 	return q.db.TryAcquireLock(ctx, id)
 }
 
-func (q *querier) UnarchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (q *querier) UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	chat, err := q.db.GetChatByID(ctx, id)
 	if err != nil {
-		return err
+		return nil, err
 	}
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
-		return err
+		return nil, err
 	}
 	return q.db.UnarchiveChatByID(ctx, id)
 }
@@ -5707,6 +5871,58 @@ func (q *querier) UpdateAPIKeyByID(ctx context.Context, arg database.UpdateAPIKe
 	return update(q.log, q.auth, fetch, q.db.UpdateAPIKeyByID)(ctx, arg)
 }
 
+func (q *querier) UpdateChatAutomation(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
+	fetchFunc := func(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
+		return q.db.GetChatAutomationByID(ctx, arg.ID)
+	}
+	return updateWithReturn(q.log, q.auth, fetchFunc, q.db.UpdateChatAutomation)(ctx, arg)
+}
+
+func (q *querier) UpdateChatAutomationTrigger(ctx context.Context, arg database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return q.db.UpdateChatAutomationTrigger(ctx, arg)
+}
+
+func (q *querier) UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg database.UpdateChatAutomationTriggerLastTriggeredAtParams) error {
+	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
+	if err != nil {
+		return err
+	}
+	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
+	if err != nil {
+		return err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return err
+	}
+	return q.db.UpdateChatAutomationTriggerLastTriggeredAt(ctx, arg)
+}
+
+func (q *querier) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
+	trigger, err := q.db.GetChatAutomationTriggerByID(ctx, arg.ID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	automation, err := q.db.GetChatAutomationByID(ctx, trigger.AutomationID)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, automation); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return q.db.UpdateChatAutomationTriggerWebhookSecret(ctx, arg)
+}
+
 func (q *querier) UpdateChatBuildAgentBinding(ctx context.Context, arg database.UpdateChatBuildAgentBindingParams) (database.Chat, error) {
 	chat, err := q.db.GetChatByID(ctx, arg.ID)
 	if err != nil {
@@ -5752,6 +5968,17 @@ func (q *querier) UpdateChatLabelsByID(ctx context.Context, arg database.UpdateC
 	return q.db.UpdateChatLabelsByID(ctx, arg)
 }
 
+func (q *querier) UpdateChatLastInjectedContext(ctx context.Context, arg database.UpdateChatLastInjectedContextParams) (database.Chat, error) {
+	chat, err := q.db.GetChatByID(ctx, arg.ID)
+	if err != nil {
+		return database.Chat{}, err
+	}
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, chat); err != nil {
+		return database.Chat{}, err
+	}
+	return q.db.UpdateChatLastInjectedContext(ctx, arg)
+}
+
 func (q *querier) UpdateChatLastModelConfigByID(ctx context.Context, arg database.UpdateChatLastModelConfigByIDParams) (database.Chat, error) {
 	chat, err := q.db.GetChatByID(ctx, arg.ID)
 	if err != nil {
@@ -7333,3 +7560,7 @@ func (q *querier) ListAuthorizedAIBridgeSessionThreads(ctx context.Context, arg
 func (q *querier) GetAuthorizedChats(ctx context.Context, arg database.GetChatsParams, _ rbac.PreparedAuthorized) ([]database.GetChatsRow, error) {
 	return q.GetChats(ctx, arg)
 }
+
+func (q *querier) GetAuthorizedChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams, _ rbac.PreparedAuthorized) ([]database.ChatAutomation, error) {
+	return q.GetChatAutomations(ctx, arg)
+}

coderd/database/dbauthz/dbauthz_test.go

@@ -392,14 +392,14 @@ func (s *MethodTestSuite) TestChats() {
 	s.Run("ArchiveChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
-		dbm.EXPECT().ArchiveChatByID(gomock.Any(), chat.ID).Return(nil).AnyTimes()
-		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+		dbm.EXPECT().ArchiveChatByID(gomock.Any(), chat.ID).Return([]database.Chat{chat}, nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns([]database.Chat{chat})
 	}))
 	s.Run("UnarchiveChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
-		dbm.EXPECT().UnarchiveChatByID(gomock.Any(), chat.ID).Return(nil).AnyTimes()
-		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns()
+		dbm.EXPECT().UnarchiveChatByID(gomock.Any(), chat.ID).Return([]database.Chat{chat}, nil).AnyTimes()
+		check.Args(chat.ID).Asserts(chat, policy.ActionUpdate).Returns([]database.Chat{chat})
 	}))
 	s.Run("PinChatByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
@@ -631,7 +631,7 @@ func (s *MethodTestSuite) TestChats() {
 	s.Run("GetDefaultChatModelConfig", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		config := testutil.Fake(s.T(), faker, database.ChatModelConfig{})
 		dbm.EXPECT().GetDefaultChatModelConfig(gomock.Any()).Return(config, nil).AnyTimes()
-		check.Asserts(rbac.ResourceDeploymentConfig, policy.ActionRead).Returns(config)
+		check.Asserts(rbac.ResourceChat.WithOwner(testActorID.String()), policy.ActionRead).Returns(config)
 	}))
 	s.Run("GetChatModelConfigs", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		configA := testutil.Fake(s.T(), faker, database.ChatModelConfig{})
@@ -1121,6 +1121,10 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().CleanupDeletedMCPServerIDsFromChats(gomock.Any()).Return(nil).AnyTimes()
 		check.Args().Asserts(rbac.ResourceChat, policy.ActionUpdate)
 	}))
+	s.Run("CleanupDeletedMCPServerIDsFromChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		dbm.EXPECT().CleanupDeletedMCPServerIDsFromChatAutomations(gomock.Any()).Return(nil).AnyTimes()
+		check.Args().Asserts(rbac.ResourceChatAutomation, policy.ActionUpdate)
+	}))
 	s.Run("DeleteMCPServerConfigByID", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
 		id := uuid.New()
 		dbm.EXPECT().DeleteMCPServerConfigByID(gomock.Any(), id).Return(nil).AnyTimes()
@@ -1204,6 +1208,19 @@ func (s *MethodTestSuite) TestChats() {
 		dbm.EXPECT().UpdateChatMCPServerIDs(gomock.Any(), arg).Return(chat, nil).AnyTimes()
 		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
 	}))
+	s.Run("UpdateChatLastInjectedContext", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		chat := testutil.Fake(s.T(), faker, database.Chat{})
+		arg := database.UpdateChatLastInjectedContextParams{
+			ID: chat.ID,
+			LastInjectedContext: pqtype.NullRawMessage{
+				RawMessage: json.RawMessage(`[{"type":"text","text":"test"}]`),
+				Valid:      true,
+			},
+		}
+		dbm.EXPECT().GetChatByID(gomock.Any(), chat.ID).Return(chat, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatLastInjectedContext(gomock.Any(), arg).Return(chat, nil).AnyTimes()
+		check.Args(arg).Asserts(chat, policy.ActionUpdate).Returns(chat)
+	}))
 	s.Run("UpdateChatLastReadMessageID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		chat := testutil.Fake(s.T(), faker, database.Chat{})
 		arg := database.UpdateChatLastReadMessageIDParams{
@@ -1237,6 +1254,226 @@ func (s *MethodTestSuite) TestChats() {
 	}))
 }
 
+func (s *MethodTestSuite) TestChatAutomations() {
+	s.Run("CountChatAutomationChatCreatesInWindow", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.CountChatAutomationChatCreatesInWindowParams{
+			AutomationID: automation.ID,
+			WindowStart:  dbtime.Now().Add(-time.Hour),
+		}
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().CountChatAutomationChatCreatesInWindow(gomock.Any(), arg).Return(int64(3), nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(int64(3))
+	}))
+	s.Run("CountChatAutomationMessagesInWindow", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.CountChatAutomationMessagesInWindowParams{
+			AutomationID: automation.ID,
+			WindowStart:  dbtime.Now().Add(-time.Hour),
+		}
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().CountChatAutomationMessagesInWindow(gomock.Any(), arg).Return(int64(5), nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(int64(5))
+	}))
+	s.Run("DeleteChatAutomationByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().DeleteChatAutomationByID(gomock.Any(), automation.ID).Return(nil).AnyTimes()
+		check.Args(automation.ID).Asserts(automation, policy.ActionDelete).Returns()
+	}))
+	s.Run("DeleteChatAutomationTriggerByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeWebhook,
+		})
+		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().DeleteChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(nil).AnyTimes()
+		check.Args(trigger.ID).Asserts(automation, policy.ActionUpdate).Returns()
+	}))
+	s.Run("GetActiveChatAutomationCronTriggers", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		rows := []database.GetActiveChatAutomationCronTriggersRow{}
+		dbm.EXPECT().GetActiveChatAutomationCronTriggers(gomock.Any()).Return(rows, nil).AnyTimes()
+		check.Args().Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead).Returns(rows)
+	}))
+	s.Run("GetChatAutomationByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		check.Args(automation.ID).Asserts(automation, policy.ActionRead).Returns(automation)
+	}))
+	s.Run("GetChatAutomationEventsByAutomationID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.GetChatAutomationEventsByAutomationIDParams{
+			AutomationID: automation.ID,
+		}
+		events := []database.ChatAutomationEvent{}
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationEventsByAutomationID(gomock.Any(), arg).Return(events, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionRead).Returns(events)
+	}))
+	s.Run("GetChatAutomationTriggerByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeWebhook,
+		})
+		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		check.Args(trigger.ID).Asserts(automation, policy.ActionRead).Returns(trigger)
+	}))
+	s.Run("GetChatAutomationTriggersByAutomationID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		triggers := []database.ChatAutomationTrigger{}
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationTriggersByAutomationID(gomock.Any(), automation.ID).Return(triggers, nil).AnyTimes()
+		check.Args(automation.ID).Asserts(automation, policy.ActionRead).Returns(triggers)
+	}))
+	s.Run("GetChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		params := database.GetChatAutomationsParams{}
+		dbm.EXPECT().GetChatAutomations(gomock.Any(), params).Return([]database.ChatAutomation{}, nil).AnyTimes()
+		dbm.EXPECT().GetAuthorizedChatAutomations(gomock.Any(), params, gomock.Any()).Return([]database.ChatAutomation{}, nil).AnyTimes()
+		check.Args(params).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead).WithNotAuthorized("nil")
+	}))
+	s.Run("GetAuthorizedChatAutomations", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		params := database.GetChatAutomationsParams{}
+		dbm.EXPECT().GetAuthorizedChatAutomations(gomock.Any(), params, gomock.Any()).Return([]database.ChatAutomation{}, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomations(gomock.Any(), params).Return([]database.ChatAutomation{}, nil).AnyTimes()
+		check.Args(params, emptyPreparedAuthorized{}).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionRead)
+	}))
+	s.Run("InsertChatAutomation", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		arg := database.InsertChatAutomationParams{
+			ID:             uuid.New(),
+			OwnerID:        uuid.New(),
+			OrganizationID: uuid.New(),
+			Name:           "test-automation",
+			Description:    "test description",
+			Instructions:   "test instructions",
+			Status:         database.ChatAutomationStatusActive,
+			CreatedAt:      dbtime.Now(),
+			UpdatedAt:      dbtime.Now(),
+		}
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{
+			ID:             arg.ID,
+			OwnerID:        arg.OwnerID,
+			OrganizationID: arg.OrganizationID,
+			Status:         arg.Status,
+		})
+		dbm.EXPECT().InsertChatAutomation(gomock.Any(), arg).Return(automation, nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourceChatAutomation.WithOwner(arg.OwnerID.String()).InOrg(arg.OrganizationID), policy.ActionCreate).Returns(automation)
+	}))
+	s.Run("InsertChatAutomationEvent", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.InsertChatAutomationEventParams{
+			ID:           uuid.New(),
+			AutomationID: automation.ID,
+			ReceivedAt:   dbtime.Now(),
+			Payload:      json.RawMessage(`{}`),
+			Status:       database.ChatAutomationEventStatusFiltered,
+		}
+		event := testutil.Fake(s.T(), faker, database.ChatAutomationEvent{
+			ID:           arg.ID,
+			AutomationID: automation.ID,
+			Status:       arg.Status,
+		})
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().InsertChatAutomationEvent(gomock.Any(), arg).Return(event, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(event)
+	}))
+	s.Run("InsertChatAutomationTrigger", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.InsertChatAutomationTriggerParams{
+			ID:           uuid.New(),
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeWebhook,
+			CreatedAt:    dbtime.Now(),
+			UpdatedAt:    dbtime.Now(),
+		}
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			ID:           arg.ID,
+			AutomationID: automation.ID,
+			Type:         arg.Type,
+		})
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().InsertChatAutomationTrigger(gomock.Any(), arg).Return(trigger, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(trigger)
+	}))
+	s.Run("PurgeOldChatAutomationEvents", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		arg := database.PurgeOldChatAutomationEventsParams{
+			Before:     dbtime.Now().Add(-7 * 24 * time.Hour),
+			LimitCount: 1000,
+		}
+		dbm.EXPECT().PurgeOldChatAutomationEvents(gomock.Any(), arg).Return(int64(5), nil).AnyTimes()
+		check.Args(arg).Asserts(rbac.ResourceChatAutomation.All(), policy.ActionDelete).Returns(int64(5))
+	}))
+	s.Run("UpdateChatAutomation", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		arg := database.UpdateChatAutomationParams{
+			ID:          automation.ID,
+			Name:        "updated-name",
+			Description: "updated description",
+			Status:      database.ChatAutomationStatusActive,
+			UpdatedAt:   dbtime.Now(),
+		}
+		updated := automation
+		updated.Name = arg.Name
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatAutomation(gomock.Any(), arg).Return(updated, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
+	}))
+	s.Run("UpdateChatAutomationTrigger", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeCron,
+		})
+		arg := database.UpdateChatAutomationTriggerParams{
+			ID:        trigger.ID,
+			UpdatedAt: dbtime.Now(),
+		}
+		updated := trigger
+		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatAutomationTrigger(gomock.Any(), arg).Return(updated, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
+	}))
+	s.Run("UpdateChatAutomationTriggerLastTriggeredAt", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeCron,
+		})
+		arg := database.UpdateChatAutomationTriggerLastTriggeredAtParams{
+			ID:              trigger.ID,
+			LastTriggeredAt: dbtime.Now(),
+		}
+		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatAutomationTriggerLastTriggeredAt(gomock.Any(), arg).Return(nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns()
+	}))
+	s.Run("UpdateChatAutomationTriggerWebhookSecret", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		automation := testutil.Fake(s.T(), faker, database.ChatAutomation{Status: database.ChatAutomationStatusActive})
+		trigger := testutil.Fake(s.T(), faker, database.ChatAutomationTrigger{
+			AutomationID: automation.ID,
+			Type:         database.ChatAutomationTriggerTypeWebhook,
+		})
+		arg := database.UpdateChatAutomationTriggerWebhookSecretParams{
+			ID:        trigger.ID,
+			UpdatedAt: dbtime.Now(),
+			WebhookSecret: sql.NullString{
+				String: "new-secret",
+				Valid:  true,
+			},
+		}
+		updated := trigger
+		dbm.EXPECT().GetChatAutomationTriggerByID(gomock.Any(), trigger.ID).Return(trigger, nil).AnyTimes()
+		dbm.EXPECT().GetChatAutomationByID(gomock.Any(), automation.ID).Return(automation, nil).AnyTimes()
+		dbm.EXPECT().UpdateChatAutomationTriggerWebhookSecret(gomock.Any(), arg).Return(updated, nil).AnyTimes()
+		check.Args(arg).Asserts(automation, policy.ActionUpdate).Returns(updated)
+	}))
+}
+
 func (s *MethodTestSuite) TestFile() {
 	s.Run("GetFileByHashAndCreator", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		f := testutil.Fake(s.T(), faker, database.File{})

coderd/database/dbmetrics/querymetrics.go

@@ -160,12 +160,12 @@ func (m queryMetricsStore) AllUserIDs(ctx context.Context, includeSystem bool) (
 	return r0, r1
 }
 
-func (m queryMetricsStore) ArchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) ArchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	start := time.Now()
-	r0 := m.s.ArchiveChatByID(ctx, id)
+	r0, r1 := m.s.ArchiveChatByID(ctx, id)
 	m.queryLatencies.WithLabelValues("ArchiveChatByID").Observe(time.Since(start).Seconds())
 	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "ArchiveChatByID").Inc()
-	return r0
+	return r0, r1
 }
 
 func (m queryMetricsStore) ArchiveUnusedTemplateVersions(ctx context.Context, arg database.ArchiveUnusedTemplateVersionsParams) ([]uuid.UUID, error) {
@@ -264,6 +264,14 @@ func (m queryMetricsStore) CleanTailnetTunnels(ctx context.Context) error {
 	return r0
 }
 
+func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error {
+	start := time.Now()
+	r0 := m.s.CleanupDeletedMCPServerIDsFromChatAutomations(ctx)
+	m.queryLatencies.WithLabelValues("CleanupDeletedMCPServerIDsFromChatAutomations").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CleanupDeletedMCPServerIDsFromChatAutomations").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error {
 	start := time.Now()
 	r0 := m.s.CleanupDeletedMCPServerIDsFromChats(ctx)
@@ -296,6 +304,22 @@ func (m queryMetricsStore) CountAuditLogs(ctx context.Context, arg database.Coun
 	return r0, r1
 }
 
+func (m queryMetricsStore) CountChatAutomationChatCreatesInWindow(ctx context.Context, arg database.CountChatAutomationChatCreatesInWindowParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.CountChatAutomationChatCreatesInWindow(ctx, arg)
+	m.queryLatencies.WithLabelValues("CountChatAutomationChatCreatesInWindow").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CountChatAutomationChatCreatesInWindow").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) CountChatAutomationMessagesInWindow(ctx context.Context, arg database.CountChatAutomationMessagesInWindowParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.CountChatAutomationMessagesInWindow(ctx, arg)
+	m.queryLatencies.WithLabelValues("CountChatAutomationMessagesInWindow").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "CountChatAutomationMessagesInWindow").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) CountConnectionLogs(ctx context.Context, arg database.CountConnectionLogsParams) (int64, error) {
 	start := time.Now()
 	r0, r1 := m.s.CountConnectionLogs(ctx, arg)
@@ -400,6 +424,22 @@ func (m queryMetricsStore) DeleteApplicationConnectAPIKeysByUserID(ctx context.C
 	return r0
 }
 
+func (m queryMetricsStore) DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.DeleteChatAutomationByID(ctx, id)
+	m.queryLatencies.WithLabelValues("DeleteChatAutomationByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatAutomationByID").Inc()
+	return r0
+}
+
+func (m queryMetricsStore) DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error {
+	start := time.Now()
+	r0 := m.s.DeleteChatAutomationTriggerByID(ctx, id)
+	m.queryLatencies.WithLabelValues("DeleteChatAutomationTriggerByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "DeleteChatAutomationTriggerByID").Inc()
+	return r0
+}
+
 func (m queryMetricsStore) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
 	start := time.Now()
 	r0 := m.s.DeleteChatModelConfigByID(ctx, id)
@@ -936,6 +976,14 @@ func (m queryMetricsStore) GetActiveAISeatCount(ctx context.Context) (int64, err
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetActiveChatAutomationCronTriggers(ctx context.Context) ([]database.GetActiveChatAutomationCronTriggersRow, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetActiveChatAutomationCronTriggers(ctx)
+	m.queryLatencies.WithLabelValues("GetActiveChatAutomationCronTriggers").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetActiveChatAutomationCronTriggers").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetActivePresetPrebuildSchedules(ctx)
@@ -1032,6 +1080,46 @@ func (m queryMetricsStore) GetAuthorizationUserRoles(ctx context.Context, userID
 	return r0, r1
 }
 
+func (m queryMetricsStore) GetChatAutomationByID(ctx context.Context, id uuid.UUID) (database.ChatAutomation, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatAutomationByID(ctx, id)
+	m.queryLatencies.WithLabelValues("GetChatAutomationByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationByID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatAutomationEventsByAutomationID(ctx context.Context, arg database.GetChatAutomationEventsByAutomationIDParams) ([]database.ChatAutomationEvent, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatAutomationEventsByAutomationID(ctx, arg)
+	m.queryLatencies.WithLabelValues("GetChatAutomationEventsByAutomationID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationEventsByAutomationID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatAutomationTriggerByID(ctx, id)
+	m.queryLatencies.WithLabelValues("GetChatAutomationTriggerByID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationTriggerByID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatAutomationTriggersByAutomationID(ctx, automationID)
+	m.queryLatencies.WithLabelValues("GetChatAutomationTriggersByAutomationID").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomationTriggersByAutomationID").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) GetChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams) ([]database.ChatAutomation, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetChatAutomations(ctx, arg)
+	m.queryLatencies.WithLabelValues("GetChatAutomations").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetChatAutomations").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) GetChatByID(ctx context.Context, id uuid.UUID) (database.Chat, error) {
 	start := time.Now()
 	r0, r1 := m.s.GetChatByID(ctx, id)
@@ -3224,6 +3312,30 @@ func (m queryMetricsStore) InsertChat(ctx context.Context, arg database.InsertCh
 	return r0, r1
 }
 
+func (m queryMetricsStore) InsertChatAutomation(ctx context.Context, arg database.InsertChatAutomationParams) (database.ChatAutomation, error) {
+	start := time.Now()
+	r0, r1 := m.s.InsertChatAutomation(ctx, arg)
+	m.queryLatencies.WithLabelValues("InsertChatAutomation").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomation").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) InsertChatAutomationEvent(ctx context.Context, arg database.InsertChatAutomationEventParams) (database.ChatAutomationEvent, error) {
+	start := time.Now()
+	r0, r1 := m.s.InsertChatAutomationEvent(ctx, arg)
+	m.queryLatencies.WithLabelValues("InsertChatAutomationEvent").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomationEvent").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) InsertChatAutomationTrigger(ctx context.Context, arg database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	start := time.Now()
+	r0, r1 := m.s.InsertChatAutomationTrigger(ctx, arg)
+	m.queryLatencies.WithLabelValues("InsertChatAutomationTrigger").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "InsertChatAutomationTrigger").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	start := time.Now()
 	r0, r1 := m.s.InsertChatFile(ctx, arg)
@@ -3952,6 +4064,14 @@ func (m queryMetricsStore) PopNextQueuedMessage(ctx context.Context, chatID uuid
 	return r0, r1
 }
 
+func (m queryMetricsStore) PurgeOldChatAutomationEvents(ctx context.Context, arg database.PurgeOldChatAutomationEventsParams) (int64, error) {
+	start := time.Now()
+	r0, r1 := m.s.PurgeOldChatAutomationEvents(ctx, arg)
+	m.queryLatencies.WithLabelValues("PurgeOldChatAutomationEvents").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "PurgeOldChatAutomationEvents").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error {
 	start := time.Now()
 	r0 := m.s.ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx, templateID)
@@ -4024,12 +4144,12 @@ func (m queryMetricsStore) TryAcquireLock(ctx context.Context, pgTryAdvisoryXact
 	return r0, r1
 }
 
-func (m queryMetricsStore) UnarchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (m queryMetricsStore) UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	start := time.Now()
-	r0 := m.s.UnarchiveChatByID(ctx, id)
+	r0, r1 := m.s.UnarchiveChatByID(ctx, id)
 	m.queryLatencies.WithLabelValues("UnarchiveChatByID").Observe(time.Since(start).Seconds())
 	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UnarchiveChatByID").Inc()
-	return r0
+	return r0, r1
 }
 
 func (m queryMetricsStore) UnarchiveTemplateVersion(ctx context.Context, arg database.UnarchiveTemplateVersionParams) error {
@@ -4080,6 +4200,38 @@ func (m queryMetricsStore) UpdateAPIKeyByID(ctx context.Context, arg database.Up
 	return r0
 }
 
+func (m queryMetricsStore) UpdateChatAutomation(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatAutomation(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatAutomation").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomation").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) UpdateChatAutomationTrigger(ctx context.Context, arg database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatAutomationTrigger(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatAutomationTrigger").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTrigger").Inc()
+	return r0, r1
+}
+
+func (m queryMetricsStore) UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg database.UpdateChatAutomationTriggerLastTriggeredAtParams) error {
+	start := time.Now()
+	r0 := m.s.UpdateChatAutomationTriggerLastTriggeredAt(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatAutomationTriggerLastTriggeredAt").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTriggerLastTriggeredAt").Inc()
+	return r0
+}
+
+func (m queryMetricsStore) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatAutomationTriggerWebhookSecret(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatAutomationTriggerWebhookSecret").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatAutomationTriggerWebhookSecret").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateChatBuildAgentBinding(ctx context.Context, arg database.UpdateChatBuildAgentBindingParams) (database.Chat, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdateChatBuildAgentBinding(ctx, arg)
@@ -4112,6 +4264,14 @@ func (m queryMetricsStore) UpdateChatLabelsByID(ctx context.Context, arg databas
 	return r0, r1
 }
 
+func (m queryMetricsStore) UpdateChatLastInjectedContext(ctx context.Context, arg database.UpdateChatLastInjectedContextParams) (database.Chat, error) {
+	start := time.Now()
+	r0, r1 := m.s.UpdateChatLastInjectedContext(ctx, arg)
+	m.queryLatencies.WithLabelValues("UpdateChatLastInjectedContext").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "UpdateChatLastInjectedContext").Inc()
+	return r0, r1
+}
+
 func (m queryMetricsStore) UpdateChatLastModelConfigByID(ctx context.Context, arg database.UpdateChatLastModelConfigByIDParams) (database.Chat, error) {
 	start := time.Now()
 	r0, r1 := m.s.UpdateChatLastModelConfigByID(ctx, arg)
@@ -5343,3 +5503,11 @@ func (m queryMetricsStore) GetAuthorizedChats(ctx context.Context, arg database.
 	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetAuthorizedChats").Inc()
 	return r0, r1
 }
+
+func (m queryMetricsStore) GetAuthorizedChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams, prepared rbac.PreparedAuthorized) ([]database.ChatAutomation, error) {
+	start := time.Now()
+	r0, r1 := m.s.GetAuthorizedChatAutomations(ctx, arg, prepared)
+	m.queryLatencies.WithLabelValues("GetAuthorizedChatAutomations").Observe(time.Since(start).Seconds())
+	m.queryCounts.WithLabelValues(httpmw.ExtractHTTPRoute(ctx), httpmw.ExtractHTTPMethod(ctx), "GetAuthorizedChatAutomations").Inc()
+	return r0, r1
+}

coderd/database/dbmock/dbmock.go

@@ -148,11 +148,12 @@ func (mr *MockStoreMockRecorder) AllUserIDs(ctx, includeSystem any) *gomock.Call
 }
 
 // ArchiveChatByID mocks base method.
-func (m *MockStore) ArchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (m *MockStore) ArchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	m.ctrl.T.Helper()
 	ret := m.ctrl.Call(m, "ArchiveChatByID", ctx, id)
-	ret0, _ := ret[0].(error)
-	return ret0
+	ret0, _ := ret[0].([]database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
 }
 
 // ArchiveChatByID indicates an expected call of ArchiveChatByID.
@@ -334,6 +335,20 @@ func (mr *MockStoreMockRecorder) CleanTailnetTunnels(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CleanTailnetTunnels", reflect.TypeOf((*MockStore)(nil).CleanTailnetTunnels), ctx)
 }
 
+// CleanupDeletedMCPServerIDsFromChatAutomations mocks base method.
+func (m *MockStore) CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "CleanupDeletedMCPServerIDsFromChatAutomations", ctx)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// CleanupDeletedMCPServerIDsFromChatAutomations indicates an expected call of CleanupDeletedMCPServerIDsFromChatAutomations.
+func (mr *MockStoreMockRecorder) CleanupDeletedMCPServerIDsFromChatAutomations(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CleanupDeletedMCPServerIDsFromChatAutomations", reflect.TypeOf((*MockStore)(nil).CleanupDeletedMCPServerIDsFromChatAutomations), ctx)
+}
+
 // CleanupDeletedMCPServerIDsFromChats mocks base method.
 func (m *MockStore) CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error {
 	m.ctrl.T.Helper()
@@ -453,6 +468,36 @@ func (mr *MockStoreMockRecorder) CountAuthorizedConnectionLogs(ctx, arg, prepare
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CountAuthorizedConnectionLogs", reflect.TypeOf((*MockStore)(nil).CountAuthorizedConnectionLogs), ctx, arg, prepared)
 }
 
+// CountChatAutomationChatCreatesInWindow mocks base method.
+func (m *MockStore) CountChatAutomationChatCreatesInWindow(ctx context.Context, arg database.CountChatAutomationChatCreatesInWindowParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "CountChatAutomationChatCreatesInWindow", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// CountChatAutomationChatCreatesInWindow indicates an expected call of CountChatAutomationChatCreatesInWindow.
+func (mr *MockStoreMockRecorder) CountChatAutomationChatCreatesInWindow(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CountChatAutomationChatCreatesInWindow", reflect.TypeOf((*MockStore)(nil).CountChatAutomationChatCreatesInWindow), ctx, arg)
+}
+
+// CountChatAutomationMessagesInWindow mocks base method.
+func (m *MockStore) CountChatAutomationMessagesInWindow(ctx context.Context, arg database.CountChatAutomationMessagesInWindowParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "CountChatAutomationMessagesInWindow", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// CountChatAutomationMessagesInWindow indicates an expected call of CountChatAutomationMessagesInWindow.
+func (mr *MockStoreMockRecorder) CountChatAutomationMessagesInWindow(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "CountChatAutomationMessagesInWindow", reflect.TypeOf((*MockStore)(nil).CountChatAutomationMessagesInWindow), ctx, arg)
+}
+
 // CountConnectionLogs mocks base method.
 func (m *MockStore) CountConnectionLogs(ctx context.Context, arg database.CountConnectionLogsParams) (int64, error) {
 	m.ctrl.T.Helper()
@@ -642,6 +687,34 @@ func (mr *MockStoreMockRecorder) DeleteApplicationConnectAPIKeysByUserID(ctx, us
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteApplicationConnectAPIKeysByUserID", reflect.TypeOf((*MockStore)(nil).DeleteApplicationConnectAPIKeysByUserID), ctx, userID)
 }
 
+// DeleteChatAutomationByID mocks base method.
+func (m *MockStore) DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteChatAutomationByID", ctx, id)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// DeleteChatAutomationByID indicates an expected call of DeleteChatAutomationByID.
+func (mr *MockStoreMockRecorder) DeleteChatAutomationByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteChatAutomationByID", reflect.TypeOf((*MockStore)(nil).DeleteChatAutomationByID), ctx, id)
+}
+
+// DeleteChatAutomationTriggerByID mocks base method.
+func (m *MockStore) DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteChatAutomationTriggerByID", ctx, id)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// DeleteChatAutomationTriggerByID indicates an expected call of DeleteChatAutomationTriggerByID.
+func (mr *MockStoreMockRecorder) DeleteChatAutomationTriggerByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteChatAutomationTriggerByID", reflect.TypeOf((*MockStore)(nil).DeleteChatAutomationTriggerByID), ctx, id)
+}
+
 // DeleteChatModelConfigByID mocks base method.
 func (m *MockStore) DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error {
 	m.ctrl.T.Helper()
@@ -1608,6 +1681,21 @@ func (mr *MockStoreMockRecorder) GetActiveAISeatCount(ctx any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveAISeatCount", reflect.TypeOf((*MockStore)(nil).GetActiveAISeatCount), ctx)
 }
 
+// GetActiveChatAutomationCronTriggers mocks base method.
+func (m *MockStore) GetActiveChatAutomationCronTriggers(ctx context.Context) ([]database.GetActiveChatAutomationCronTriggersRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetActiveChatAutomationCronTriggers", ctx)
+	ret0, _ := ret[0].([]database.GetActiveChatAutomationCronTriggersRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetActiveChatAutomationCronTriggers indicates an expected call of GetActiveChatAutomationCronTriggers.
+func (mr *MockStoreMockRecorder) GetActiveChatAutomationCronTriggers(ctx any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetActiveChatAutomationCronTriggers", reflect.TypeOf((*MockStore)(nil).GetActiveChatAutomationCronTriggers), ctx)
+}
+
 // GetActivePresetPrebuildSchedules mocks base method.
 func (m *MockStore) GetActivePresetPrebuildSchedules(ctx context.Context) ([]database.TemplateVersionPresetPrebuildSchedule, error) {
 	m.ctrl.T.Helper()
@@ -1803,6 +1891,21 @@ func (mr *MockStoreMockRecorder) GetAuthorizedAuditLogsOffset(ctx, arg, prepared
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetAuthorizedAuditLogsOffset", reflect.TypeOf((*MockStore)(nil).GetAuthorizedAuditLogsOffset), ctx, arg, prepared)
 }
 
+// GetAuthorizedChatAutomations mocks base method.
+func (m *MockStore) GetAuthorizedChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams, prepared rbac.PreparedAuthorized) ([]database.ChatAutomation, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetAuthorizedChatAutomations", ctx, arg, prepared)
+	ret0, _ := ret[0].([]database.ChatAutomation)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetAuthorizedChatAutomations indicates an expected call of GetAuthorizedChatAutomations.
+func (mr *MockStoreMockRecorder) GetAuthorizedChatAutomations(ctx, arg, prepared any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetAuthorizedChatAutomations", reflect.TypeOf((*MockStore)(nil).GetAuthorizedChatAutomations), ctx, arg, prepared)
+}
+
 // GetAuthorizedChats mocks base method.
 func (m *MockStore) GetAuthorizedChats(ctx context.Context, arg database.GetChatsParams, prepared rbac.PreparedAuthorized) ([]database.GetChatsRow, error) {
 	m.ctrl.T.Helper()
@@ -1893,6 +1996,81 @@ func (mr *MockStoreMockRecorder) GetAuthorizedWorkspacesAndAgentsByOwnerID(ctx,
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetAuthorizedWorkspacesAndAgentsByOwnerID", reflect.TypeOf((*MockStore)(nil).GetAuthorizedWorkspacesAndAgentsByOwnerID), ctx, ownerID, prepared)
 }
 
+// GetChatAutomationByID mocks base method.
+func (m *MockStore) GetChatAutomationByID(ctx context.Context, id uuid.UUID) (database.ChatAutomation, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatAutomationByID", ctx, id)
+	ret0, _ := ret[0].(database.ChatAutomation)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatAutomationByID indicates an expected call of GetChatAutomationByID.
+func (mr *MockStoreMockRecorder) GetChatAutomationByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatAutomationByID", reflect.TypeOf((*MockStore)(nil).GetChatAutomationByID), ctx, id)
+}
+
+// GetChatAutomationEventsByAutomationID mocks base method.
+func (m *MockStore) GetChatAutomationEventsByAutomationID(ctx context.Context, arg database.GetChatAutomationEventsByAutomationIDParams) ([]database.ChatAutomationEvent, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatAutomationEventsByAutomationID", ctx, arg)
+	ret0, _ := ret[0].([]database.ChatAutomationEvent)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatAutomationEventsByAutomationID indicates an expected call of GetChatAutomationEventsByAutomationID.
+func (mr *MockStoreMockRecorder) GetChatAutomationEventsByAutomationID(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatAutomationEventsByAutomationID", reflect.TypeOf((*MockStore)(nil).GetChatAutomationEventsByAutomationID), ctx, arg)
+}
+
+// GetChatAutomationTriggerByID mocks base method.
+func (m *MockStore) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatAutomationTriggerByID", ctx, id)
+	ret0, _ := ret[0].(database.ChatAutomationTrigger)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatAutomationTriggerByID indicates an expected call of GetChatAutomationTriggerByID.
+func (mr *MockStoreMockRecorder) GetChatAutomationTriggerByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatAutomationTriggerByID", reflect.TypeOf((*MockStore)(nil).GetChatAutomationTriggerByID), ctx, id)
+}
+
+// GetChatAutomationTriggersByAutomationID mocks base method.
+func (m *MockStore) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatAutomationTriggersByAutomationID", ctx, automationID)
+	ret0, _ := ret[0].([]database.ChatAutomationTrigger)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatAutomationTriggersByAutomationID indicates an expected call of GetChatAutomationTriggersByAutomationID.
+func (mr *MockStoreMockRecorder) GetChatAutomationTriggersByAutomationID(ctx, automationID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatAutomationTriggersByAutomationID", reflect.TypeOf((*MockStore)(nil).GetChatAutomationTriggersByAutomationID), ctx, automationID)
+}
+
+// GetChatAutomations mocks base method.
+func (m *MockStore) GetChatAutomations(ctx context.Context, arg database.GetChatAutomationsParams) ([]database.ChatAutomation, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetChatAutomations", ctx, arg)
+	ret0, _ := ret[0].([]database.ChatAutomation)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetChatAutomations indicates an expected call of GetChatAutomations.
+func (mr *MockStoreMockRecorder) GetChatAutomations(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetChatAutomations", reflect.TypeOf((*MockStore)(nil).GetChatAutomations), ctx, arg)
+}
+
 // GetChatByID mocks base method.
 func (m *MockStore) GetChatByID(ctx context.Context, id uuid.UUID) (database.Chat, error) {
 	m.ctrl.T.Helper()
@@ -6047,6 +6225,51 @@ func (mr *MockStoreMockRecorder) InsertChat(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChat", reflect.TypeOf((*MockStore)(nil).InsertChat), ctx, arg)
 }
 
+// InsertChatAutomation mocks base method.
+func (m *MockStore) InsertChatAutomation(ctx context.Context, arg database.InsertChatAutomationParams) (database.ChatAutomation, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "InsertChatAutomation", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomation)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// InsertChatAutomation indicates an expected call of InsertChatAutomation.
+func (mr *MockStoreMockRecorder) InsertChatAutomation(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChatAutomation", reflect.TypeOf((*MockStore)(nil).InsertChatAutomation), ctx, arg)
+}
+
+// InsertChatAutomationEvent mocks base method.
+func (m *MockStore) InsertChatAutomationEvent(ctx context.Context, arg database.InsertChatAutomationEventParams) (database.ChatAutomationEvent, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "InsertChatAutomationEvent", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomationEvent)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// InsertChatAutomationEvent indicates an expected call of InsertChatAutomationEvent.
+func (mr *MockStoreMockRecorder) InsertChatAutomationEvent(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChatAutomationEvent", reflect.TypeOf((*MockStore)(nil).InsertChatAutomationEvent), ctx, arg)
+}
+
+// InsertChatAutomationTrigger mocks base method.
+func (m *MockStore) InsertChatAutomationTrigger(ctx context.Context, arg database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "InsertChatAutomationTrigger", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomationTrigger)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// InsertChatAutomationTrigger indicates an expected call of InsertChatAutomationTrigger.
+func (mr *MockStoreMockRecorder) InsertChatAutomationTrigger(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "InsertChatAutomationTrigger", reflect.TypeOf((*MockStore)(nil).InsertChatAutomationTrigger), ctx, arg)
+}
+
 // InsertChatFile mocks base method.
 func (m *MockStore) InsertChatFile(ctx context.Context, arg database.InsertChatFileParams) (database.InsertChatFileRow, error) {
 	m.ctrl.T.Helper()
@@ -7500,6 +7723,21 @@ func (mr *MockStoreMockRecorder) PopNextQueuedMessage(ctx, chatID any) *gomock.C
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "PopNextQueuedMessage", reflect.TypeOf((*MockStore)(nil).PopNextQueuedMessage), ctx, chatID)
 }
 
+// PurgeOldChatAutomationEvents mocks base method.
+func (m *MockStore) PurgeOldChatAutomationEvents(ctx context.Context, arg database.PurgeOldChatAutomationEventsParams) (int64, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "PurgeOldChatAutomationEvents", ctx, arg)
+	ret0, _ := ret[0].(int64)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// PurgeOldChatAutomationEvents indicates an expected call of PurgeOldChatAutomationEvents.
+func (mr *MockStoreMockRecorder) PurgeOldChatAutomationEvents(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "PurgeOldChatAutomationEvents", reflect.TypeOf((*MockStore)(nil).PurgeOldChatAutomationEvents), ctx, arg)
+}
+
 // ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate mocks base method.
 func (m *MockStore) ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error {
 	m.ctrl.T.Helper()
@@ -7632,11 +7870,12 @@ func (mr *MockStoreMockRecorder) TryAcquireLock(ctx, pgTryAdvisoryXactLock any)
 }
 
 // UnarchiveChatByID mocks base method.
-func (m *MockStore) UnarchiveChatByID(ctx context.Context, id uuid.UUID) error {
+func (m *MockStore) UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]database.Chat, error) {
 	m.ctrl.T.Helper()
 	ret := m.ctrl.Call(m, "UnarchiveChatByID", ctx, id)
-	ret0, _ := ret[0].(error)
-	return ret0
+	ret0, _ := ret[0].([]database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
 }
 
 // UnarchiveChatByID indicates an expected call of UnarchiveChatByID.
@@ -7730,6 +7969,65 @@ func (mr *MockStoreMockRecorder) UpdateAPIKeyByID(ctx, arg any) *gomock.Call {
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateAPIKeyByID", reflect.TypeOf((*MockStore)(nil).UpdateAPIKeyByID), ctx, arg)
 }
 
+// UpdateChatAutomation mocks base method.
+func (m *MockStore) UpdateChatAutomation(ctx context.Context, arg database.UpdateChatAutomationParams) (database.ChatAutomation, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatAutomation", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomation)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatAutomation indicates an expected call of UpdateChatAutomation.
+func (mr *MockStoreMockRecorder) UpdateChatAutomation(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatAutomation", reflect.TypeOf((*MockStore)(nil).UpdateChatAutomation), ctx, arg)
+}
+
+// UpdateChatAutomationTrigger mocks base method.
+func (m *MockStore) UpdateChatAutomationTrigger(ctx context.Context, arg database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatAutomationTrigger", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomationTrigger)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatAutomationTrigger indicates an expected call of UpdateChatAutomationTrigger.
+func (mr *MockStoreMockRecorder) UpdateChatAutomationTrigger(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatAutomationTrigger", reflect.TypeOf((*MockStore)(nil).UpdateChatAutomationTrigger), ctx, arg)
+}
+
+// UpdateChatAutomationTriggerLastTriggeredAt mocks base method.
+func (m *MockStore) UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg database.UpdateChatAutomationTriggerLastTriggeredAtParams) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatAutomationTriggerLastTriggeredAt", ctx, arg)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// UpdateChatAutomationTriggerLastTriggeredAt indicates an expected call of UpdateChatAutomationTriggerLastTriggeredAt.
+func (mr *MockStoreMockRecorder) UpdateChatAutomationTriggerLastTriggeredAt(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatAutomationTriggerLastTriggeredAt", reflect.TypeOf((*MockStore)(nil).UpdateChatAutomationTriggerLastTriggeredAt), ctx, arg)
+}
+
+// UpdateChatAutomationTriggerWebhookSecret mocks base method.
+func (m *MockStore) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatAutomationTriggerWebhookSecret", ctx, arg)
+	ret0, _ := ret[0].(database.ChatAutomationTrigger)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatAutomationTriggerWebhookSecret indicates an expected call of UpdateChatAutomationTriggerWebhookSecret.
+func (mr *MockStoreMockRecorder) UpdateChatAutomationTriggerWebhookSecret(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatAutomationTriggerWebhookSecret", reflect.TypeOf((*MockStore)(nil).UpdateChatAutomationTriggerWebhookSecret), ctx, arg)
+}
+
 // UpdateChatBuildAgentBinding mocks base method.
 func (m *MockStore) UpdateChatBuildAgentBinding(ctx context.Context, arg database.UpdateChatBuildAgentBindingParams) (database.Chat, error) {
 	m.ctrl.T.Helper()
@@ -7790,6 +8088,21 @@ func (mr *MockStoreMockRecorder) UpdateChatLabelsByID(ctx, arg any) *gomock.Call
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatLabelsByID", reflect.TypeOf((*MockStore)(nil).UpdateChatLabelsByID), ctx, arg)
 }
 
+// UpdateChatLastInjectedContext mocks base method.
+func (m *MockStore) UpdateChatLastInjectedContext(ctx context.Context, arg database.UpdateChatLastInjectedContextParams) (database.Chat, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateChatLastInjectedContext", ctx, arg)
+	ret0, _ := ret[0].(database.Chat)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateChatLastInjectedContext indicates an expected call of UpdateChatLastInjectedContext.
+func (mr *MockStoreMockRecorder) UpdateChatLastInjectedContext(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateChatLastInjectedContext", reflect.TypeOf((*MockStore)(nil).UpdateChatLastInjectedContext), ctx, arg)
+}
+
 // UpdateChatLastModelConfigByID mocks base method.
 func (m *MockStore) UpdateChatLastModelConfigByID(ctx context.Context, arg database.UpdateChatLastModelConfigByIDParams) (database.Chat, error) {
 	m.ctrl.T.Helper()

coderd/database/dump.sql

@@ -220,7 +220,12 @@ CREATE TYPE api_key_scope AS ENUM (
     'chat:read',
     'chat:update',
     'chat:delete',
-    'chat:*'
+    'chat:*',
+    'chat_automation:create',
+    'chat_automation:read',
+    'chat_automation:update',
+    'chat_automation:delete',
+    'chat_automation:*'
 );
 
 CREATE TYPE app_sharing_level AS ENUM (
@@ -270,6 +275,32 @@ CREATE TYPE build_reason AS ENUM (
     'task_resume'
 );
 
+CREATE TYPE chat_automation_event_status AS ENUM (
+    'filtered',
+    'preview',
+    'created',
+    'continued',
+    'rate_limited',
+    'error'
+);
+
+COMMENT ON TYPE chat_automation_event_status IS 'Outcome of a chat automation event: filtered, preview, created, continued, rate_limited, or error.';
+
+CREATE TYPE chat_automation_status AS ENUM (
+    'disabled',
+    'preview',
+    'active'
+);
+
+COMMENT ON TYPE chat_automation_status IS 'Lifecycle state of a chat automation: disabled, preview, or active.';
+
+CREATE TYPE chat_automation_trigger_type AS ENUM (
+    'webhook',
+    'cron'
+);
+
+COMMENT ON TYPE chat_automation_trigger_type IS 'Discriminator for chat automation triggers: webhook or cron.';
+
 CREATE TYPE chat_message_role AS ENUM (
     'system',
     'user',
@@ -1238,6 +1269,104 @@ COMMENT ON COLUMN boundary_usage_stats.window_start IS 'Start of the time window
 
 COMMENT ON COLUMN boundary_usage_stats.updated_at IS 'Timestamp of the last update to this row.';
 
+CREATE TABLE chat_automation_events (
+    id uuid NOT NULL,
+    automation_id uuid NOT NULL,
+    trigger_id uuid,
+    received_at timestamp with time zone NOT NULL,
+    payload jsonb NOT NULL,
+    filter_matched boolean NOT NULL,
+    resolved_labels jsonb,
+    matched_chat_id uuid,
+    created_chat_id uuid,
+    status chat_automation_event_status NOT NULL,
+    error text,
+    CONSTRAINT chat_automation_events_chat_exclusivity CHECK (((matched_chat_id IS NULL) OR (created_chat_id IS NULL)))
+);
+
+COMMENT ON TABLE chat_automation_events IS 'Every trigger invocation produces an event row regardless of outcome. This table is the audit trail and the data source for rate-limit window counts. Rows are append-only and expected to be purged by a background job after a retention period.';
+
+COMMENT ON COLUMN chat_automation_events.payload IS 'The raw payload that was evaluated. For webhooks this is the HTTP body; for cron triggers it is a synthetic JSON envelope with schedule metadata.';
+
+COMMENT ON COLUMN chat_automation_events.filter_matched IS 'Whether the trigger filter conditions matched. False means the event was dropped before any chat interaction.';
+
+COMMENT ON COLUMN chat_automation_events.resolved_labels IS 'Labels resolved from the payload via label_paths. Stored so the event log shows exactly which labels were computed.';
+
+COMMENT ON COLUMN chat_automation_events.matched_chat_id IS 'ID of an existing chat that was found via label matching and continued with a new message.';
+
+COMMENT ON COLUMN chat_automation_events.created_chat_id IS 'ID of a newly created chat (mutually exclusive with matched_chat_id in practice).';
+
+COMMENT ON COLUMN chat_automation_events.status IS 'Outcome of the event: filtered — filter did not match; preview — automation is in preview mode; created — new chat was created; continued — existing chat was continued; rate_limited — rate limit prevented chat action; error — something went wrong.';
+
+CREATE TABLE chat_automation_triggers (
+    id uuid NOT NULL,
+    automation_id uuid NOT NULL,
+    type chat_automation_trigger_type NOT NULL,
+    webhook_secret text,
+    webhook_secret_key_id text,
+    cron_schedule text,
+    last_triggered_at timestamp with time zone,
+    filter jsonb,
+    label_paths jsonb,
+    created_at timestamp with time zone NOT NULL,
+    updated_at timestamp with time zone NOT NULL,
+    CONSTRAINT chat_automation_triggers_cron_fields CHECK (((type <> 'cron'::chat_automation_trigger_type) OR ((cron_schedule IS NOT NULL) AND (webhook_secret IS NULL) AND (webhook_secret_key_id IS NULL)))),
+    CONSTRAINT chat_automation_triggers_webhook_fields CHECK (((type <> 'webhook'::chat_automation_trigger_type) OR ((webhook_secret IS NOT NULL) AND (cron_schedule IS NULL) AND (last_triggered_at IS NULL))))
+);
+
+COMMENT ON TABLE chat_automation_triggers IS 'Triggers define how an automation is invoked. Each automation can have multiple triggers (e.g. one webhook + one cron schedule). Webhook and cron triggers share the same row shape with type-specific nullable columns to keep the schema simple.';
+
+COMMENT ON COLUMN chat_automation_triggers.type IS 'Discriminator: webhook or cron. Determines which nullable columns are meaningful.';
+
+COMMENT ON COLUMN chat_automation_triggers.webhook_secret IS 'HMAC-SHA256 shared secret for webhook signature verification (X-Hub-Signature-256 header). NULL for cron triggers.';
+
+COMMENT ON COLUMN chat_automation_triggers.cron_schedule IS 'Standard 5-field cron expression (minute hour dom month dow), with optional CRON_TZ= prefix. NULL for webhook triggers.';
+
+COMMENT ON COLUMN chat_automation_triggers.last_triggered_at IS 'Timestamp of the last successful cron fire. The scheduler computes next = cron.Next(last_triggered_at) and fires when next <= now. NULL means the trigger has never fired. Not used for webhook triggers.';
+
+COMMENT ON COLUMN chat_automation_triggers.filter IS 'gjson path-to-value filter conditions evaluated against the incoming webhook payload. All conditions must match for the trigger to fire. NULL or empty means match everything.';
+
+COMMENT ON COLUMN chat_automation_triggers.label_paths IS 'Maps chat label keys to gjson paths. When a trigger fires, labels are resolved from the payload and used to find an existing chat to continue (by label match) or set on a newly created chat.';
+
+CREATE TABLE chat_automations (
+    id uuid NOT NULL,
+    owner_id uuid NOT NULL,
+    organization_id uuid NOT NULL,
+    name text NOT NULL,
+    description text DEFAULT ''::text NOT NULL,
+    instructions text DEFAULT ''::text NOT NULL,
+    model_config_id uuid,
+    mcp_server_ids uuid[] DEFAULT '{}'::uuid[] NOT NULL,
+    allowed_tools text[] DEFAULT '{}'::text[] NOT NULL,
+    status chat_automation_status DEFAULT 'disabled'::chat_automation_status NOT NULL,
+    max_chat_creates_per_hour integer DEFAULT 10 NOT NULL,
+    max_messages_per_hour integer DEFAULT 60 NOT NULL,
+    created_at timestamp with time zone NOT NULL,
+    updated_at timestamp with time zone NOT NULL,
+    CONSTRAINT chat_automations_max_chat_creates_per_hour_check CHECK ((max_chat_creates_per_hour > 0)),
+    CONSTRAINT chat_automations_max_messages_per_hour_check CHECK ((max_messages_per_hour > 0))
+);
+
+COMMENT ON TABLE chat_automations IS 'Chat automations bridge external events (webhooks, cron schedules) to Coder chats. A chat automation defines what to say, which model and tools to use, and how fast it is allowed to create or continue chats.';
+
+COMMENT ON COLUMN chat_automations.owner_id IS 'The user on whose behalf chats are created. All RBAC checks and chat ownership are scoped to this user.';
+
+COMMENT ON COLUMN chat_automations.organization_id IS 'Organization scope for RBAC. Combined with owner_id and name to form a unique constraint so automations are namespaced per user per org.';
+
+COMMENT ON COLUMN chat_automations.instructions IS 'The user-role message injected into every chat this automation creates. This is the core prompt that tells the LLM what to do.';
+
+COMMENT ON COLUMN chat_automations.model_config_id IS 'Optional model configuration override. When NULL the deployment default is used. SET NULL on delete so automations survive config changes gracefully.';
+
+COMMENT ON COLUMN chat_automations.mcp_server_ids IS 'MCP servers to attach to chats created by this automation. Stored as an array of UUIDs rather than a join table because the set is small and always read/written atomically.';
+
+COMMENT ON COLUMN chat_automations.allowed_tools IS 'Tool allowlist. Empty means all tools available to the model config are permitted.';
+
+COMMENT ON COLUMN chat_automations.status IS 'Lifecycle state: disabled — trigger events are silently dropped; preview — events are logged but no chat is created (dry-run); active — events create or continue chats.';
+
+COMMENT ON COLUMN chat_automations.max_chat_creates_per_hour IS 'Maximum number of new chats this automation may create in a rolling one-hour window. Prevents runaway webhook storms from flooding the system.';
+
+COMMENT ON COLUMN chat_automations.max_messages_per_hour IS 'Maximum total messages (creates + continues) this automation may send in a rolling one-hour window. A second, broader throttle that catches high-frequency continuation patterns.';
+
 CREATE TABLE chat_diff_statuses (
     chat_id uuid NOT NULL,
     url text,
@@ -1403,7 +1532,9 @@ CREATE TABLE chats (
     build_id uuid,
     agent_id uuid,
     pin_order integer DEFAULT 0 NOT NULL,
-    last_read_message_id bigint
+    last_read_message_id bigint,
+    last_injected_context jsonb,
+    automation_id uuid
 );
 
 CREATE TABLE connection_logs (
@@ -3319,6 +3450,15 @@ ALTER TABLE ONLY audit_logs
 ALTER TABLE ONLY boundary_usage_stats
     ADD CONSTRAINT boundary_usage_stats_pkey PRIMARY KEY (replica_id);
 
+ALTER TABLE ONLY chat_automation_events
+    ADD CONSTRAINT chat_automation_events_pkey PRIMARY KEY (id);
+
+ALTER TABLE ONLY chat_automation_triggers
+    ADD CONSTRAINT chat_automation_triggers_pkey PRIMARY KEY (id);
+
+ALTER TABLE ONLY chat_automations
+    ADD CONSTRAINT chat_automations_pkey PRIMARY KEY (id);
+
 ALTER TABLE ONLY chat_diff_statuses
     ADD CONSTRAINT chat_diff_statuses_pkey PRIMARY KEY (chat_id);
 
@@ -3704,6 +3844,20 @@ CREATE INDEX idx_audit_log_user_id ON audit_logs USING btree (user_id);
 
 CREATE INDEX idx_audit_logs_time_desc ON audit_logs USING btree ("time" DESC);
 
+CREATE INDEX idx_chat_automation_events_automation_id_received_at ON chat_automation_events USING btree (automation_id, received_at DESC);
+
+CREATE INDEX idx_chat_automation_events_rate_limit ON chat_automation_events USING btree (automation_id, received_at) WHERE (status = ANY (ARRAY['created'::chat_automation_event_status, 'continued'::chat_automation_event_status]));
+
+CREATE INDEX idx_chat_automation_events_received_at ON chat_automation_events USING btree (received_at);
+
+CREATE INDEX idx_chat_automation_triggers_automation_id ON chat_automation_triggers USING btree (automation_id);
+
+CREATE INDEX idx_chat_automations_organization_id ON chat_automations USING btree (organization_id);
+
+CREATE INDEX idx_chat_automations_owner_id ON chat_automations USING btree (owner_id);
+
+CREATE UNIQUE INDEX idx_chat_automations_owner_org_name ON chat_automations USING btree (owner_id, organization_id, name);
+
 CREATE INDEX idx_chat_diff_statuses_stale_at ON chat_diff_statuses USING btree (stale_at);
 
 CREATE INDEX idx_chat_files_org ON chat_files USING btree (organization_id);
@@ -3732,6 +3886,8 @@ CREATE INDEX idx_chat_providers_enabled ON chat_providers USING btree (enabled);
 
 CREATE INDEX idx_chat_queued_messages_chat_id ON chat_queued_messages USING btree (chat_id);
 
+CREATE INDEX idx_chats_automation_id ON chats USING btree (automation_id);
+
 CREATE INDEX idx_chats_labels ON chats USING gin (labels);
 
 CREATE INDEX idx_chats_last_model_config_id ON chats USING btree (last_model_config_id);
@@ -4005,6 +4161,33 @@ ALTER TABLE ONLY aibridge_interceptions
 ALTER TABLE ONLY api_keys
     ADD CONSTRAINT api_keys_user_id_uuid_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 
+ALTER TABLE ONLY chat_automation_events
+    ADD CONSTRAINT chat_automation_events_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY chat_automation_events
+    ADD CONSTRAINT chat_automation_events_created_chat_id_fkey FOREIGN KEY (created_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
+
+ALTER TABLE ONLY chat_automation_events
+    ADD CONSTRAINT chat_automation_events_matched_chat_id_fkey FOREIGN KEY (matched_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
+
+ALTER TABLE ONLY chat_automation_events
+    ADD CONSTRAINT chat_automation_events_trigger_id_fkey FOREIGN KEY (trigger_id) REFERENCES chat_automation_triggers(id) ON DELETE SET NULL;
+
+ALTER TABLE ONLY chat_automation_triggers
+    ADD CONSTRAINT chat_automation_triggers_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY chat_automation_triggers
+    ADD CONSTRAINT chat_automation_triggers_webhook_secret_key_id_fkey FOREIGN KEY (webhook_secret_key_id) REFERENCES dbcrypt_keys(active_key_digest);
+
+ALTER TABLE ONLY chat_automations
+    ADD CONSTRAINT chat_automations_model_config_id_fkey FOREIGN KEY (model_config_id) REFERENCES chat_model_configs(id) ON DELETE SET NULL;
+
+ALTER TABLE ONLY chat_automations
+    ADD CONSTRAINT chat_automations_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
+
+ALTER TABLE ONLY chat_automations
+    ADD CONSTRAINT chat_automations_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
+
 ALTER TABLE ONLY chat_diff_statuses
     ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 
@@ -4041,6 +4224,9 @@ ALTER TABLE ONLY chat_queued_messages
 ALTER TABLE ONLY chats
     ADD CONSTRAINT chats_agent_id_fkey FOREIGN KEY (agent_id) REFERENCES workspace_agents(id) ON DELETE SET NULL;
 
+ALTER TABLE ONLY chats
+    ADD CONSTRAINT chats_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE SET NULL;
+
 ALTER TABLE ONLY chats
     ADD CONSTRAINT chats_build_id_fkey FOREIGN KEY (build_id) REFERENCES workspace_builds(id) ON DELETE SET NULL;
 

coderd/database/foreign_key_constraint.go

@@ -9,6 +9,15 @@ const (
 	ForeignKeyAiSeatStateUserID                                   ForeignKeyConstraint = "ai_seat_state_user_id_fkey"                                      // ALTER TABLE ONLY ai_seat_state ADD CONSTRAINT ai_seat_state_user_id_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyAibridgeInterceptionsInitiatorID                    ForeignKeyConstraint = "aibridge_interceptions_initiator_id_fkey"                        // ALTER TABLE ONLY aibridge_interceptions ADD CONSTRAINT aibridge_interceptions_initiator_id_fkey FOREIGN KEY (initiator_id) REFERENCES users(id);
 	ForeignKeyAPIKeysUserIDUUID                                   ForeignKeyConstraint = "api_keys_user_id_uuid_fkey"                                      // ALTER TABLE ONLY api_keys ADD CONSTRAINT api_keys_user_id_uuid_fkey FOREIGN KEY (user_id) REFERENCES users(id) ON DELETE CASCADE;
+	ForeignKeyChatAutomationEventsAutomationID                    ForeignKeyConstraint = "chat_automation_events_automation_id_fkey"                       // ALTER TABLE ONLY chat_automation_events ADD CONSTRAINT chat_automation_events_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
+	ForeignKeyChatAutomationEventsCreatedChatID                   ForeignKeyConstraint = "chat_automation_events_created_chat_id_fkey"                     // ALTER TABLE ONLY chat_automation_events ADD CONSTRAINT chat_automation_events_created_chat_id_fkey FOREIGN KEY (created_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
+	ForeignKeyChatAutomationEventsMatchedChatID                   ForeignKeyConstraint = "chat_automation_events_matched_chat_id_fkey"                     // ALTER TABLE ONLY chat_automation_events ADD CONSTRAINT chat_automation_events_matched_chat_id_fkey FOREIGN KEY (matched_chat_id) REFERENCES chats(id) ON DELETE SET NULL;
+	ForeignKeyChatAutomationEventsTriggerID                       ForeignKeyConstraint = "chat_automation_events_trigger_id_fkey"                          // ALTER TABLE ONLY chat_automation_events ADD CONSTRAINT chat_automation_events_trigger_id_fkey FOREIGN KEY (trigger_id) REFERENCES chat_automation_triggers(id) ON DELETE SET NULL;
+	ForeignKeyChatAutomationTriggersAutomationID                  ForeignKeyConstraint = "chat_automation_triggers_automation_id_fkey"                     // ALTER TABLE ONLY chat_automation_triggers ADD CONSTRAINT chat_automation_triggers_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE;
+	ForeignKeyChatAutomationTriggersWebhookSecretKeyID            ForeignKeyConstraint = "chat_automation_triggers_webhook_secret_key_id_fkey"             // ALTER TABLE ONLY chat_automation_triggers ADD CONSTRAINT chat_automation_triggers_webhook_secret_key_id_fkey FOREIGN KEY (webhook_secret_key_id) REFERENCES dbcrypt_keys(active_key_digest);
+	ForeignKeyChatAutomationsModelConfigID                        ForeignKeyConstraint = "chat_automations_model_config_id_fkey"                           // ALTER TABLE ONLY chat_automations ADD CONSTRAINT chat_automations_model_config_id_fkey FOREIGN KEY (model_config_id) REFERENCES chat_model_configs(id) ON DELETE SET NULL;
+	ForeignKeyChatAutomationsOrganizationID                       ForeignKeyConstraint = "chat_automations_organization_id_fkey"                           // ALTER TABLE ONLY chat_automations ADD CONSTRAINT chat_automations_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
+	ForeignKeyChatAutomationsOwnerID                              ForeignKeyConstraint = "chat_automations_owner_id_fkey"                                  // ALTER TABLE ONLY chat_automations ADD CONSTRAINT chat_automations_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
 	ForeignKeyChatDiffStatusesChatID                              ForeignKeyConstraint = "chat_diff_statuses_chat_id_fkey"                                 // ALTER TABLE ONLY chat_diff_statuses ADD CONSTRAINT chat_diff_statuses_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 	ForeignKeyChatFilesOrganizationID                             ForeignKeyConstraint = "chat_files_organization_id_fkey"                                 // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_organization_id_fkey FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE;
 	ForeignKeyChatFilesOwnerID                                    ForeignKeyConstraint = "chat_files_owner_id_fkey"                                        // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;
@@ -21,6 +30,7 @@ const (
 	ForeignKeyChatProvidersCreatedBy                              ForeignKeyConstraint = "chat_providers_created_by_fkey"                                  // ALTER TABLE ONLY chat_providers ADD CONSTRAINT chat_providers_created_by_fkey FOREIGN KEY (created_by) REFERENCES users(id);
 	ForeignKeyChatQueuedMessagesChatID                            ForeignKeyConstraint = "chat_queued_messages_chat_id_fkey"                               // ALTER TABLE ONLY chat_queued_messages ADD CONSTRAINT chat_queued_messages_chat_id_fkey FOREIGN KEY (chat_id) REFERENCES chats(id) ON DELETE CASCADE;
 	ForeignKeyChatsAgentID                                        ForeignKeyConstraint = "chats_agent_id_fkey"                                             // ALTER TABLE ONLY chats ADD CONSTRAINT chats_agent_id_fkey FOREIGN KEY (agent_id) REFERENCES workspace_agents(id) ON DELETE SET NULL;
+	ForeignKeyChatsAutomationID                                   ForeignKeyConstraint = "chats_automation_id_fkey"                                        // ALTER TABLE ONLY chats ADD CONSTRAINT chats_automation_id_fkey FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE SET NULL;
 	ForeignKeyChatsBuildID                                        ForeignKeyConstraint = "chats_build_id_fkey"                                             // ALTER TABLE ONLY chats ADD CONSTRAINT chats_build_id_fkey FOREIGN KEY (build_id) REFERENCES workspace_builds(id) ON DELETE SET NULL;
 	ForeignKeyChatsLastModelConfigID                              ForeignKeyConstraint = "chats_last_model_config_id_fkey"                                 // ALTER TABLE ONLY chats ADD CONSTRAINT chats_last_model_config_id_fkey FOREIGN KEY (last_model_config_id) REFERENCES chat_model_configs(id);
 	ForeignKeyChatsOwnerID                                        ForeignKeyConstraint = "chats_owner_id_fkey"                                             // ALTER TABLE ONLY chats ADD CONSTRAINT chats_owner_id_fkey FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE;

coderd/database/gentest/modelqueries_test.go

@@ -27,6 +27,7 @@ func TestCustomQueriesSyncedRowScan(t *testing.T) {
 		"GetWorkspaces":          "GetAuthorizedWorkspaces",
 		"GetUsers":               "GetAuthorizedUsers",
 		"GetChats":               "GetAuthorizedChats",
+		"GetChatAutomations":     "GetAuthorizedChatAutomations",
 	}
 
 	// Scan custom

coderd/database/lock.go

@@ -15,6 +15,9 @@ const (
 	LockIDReconcilePrebuilds
 	LockIDReconcileSystemRoles
 	LockIDBoundaryUsageStats
+	// LockIDChatAutomationCron prevents concurrent cron trigger
+	// evaluation across coderd replicas.
+	LockIDChatAutomationCron
 )
 
 // GenLockID generates a unique and consistent lock ID from a given string.

coderd/database/migrations/000456_chat_last_injected_context.down.sql

@@ -0,0 +1 @@
+ALTER TABLE chats DROP COLUMN last_injected_context;

coderd/database/migrations/000456_chat_last_injected_context.up.sql

@@ -0,0 +1 @@
+ALTER TABLE chats ADD COLUMN last_injected_context JSONB;

coderd/database/migrations/000457_chat_access_role.down.sql

@@ -0,0 +1,4 @@
+-- Remove 'agents-access' from all users who have it.
+UPDATE users
+SET rbac_roles = array_remove(rbac_roles, 'agents-access')
+WHERE 'agents-access' = ANY(rbac_roles);

coderd/database/migrations/000457_chat_access_role.up.sql

@@ -0,0 +1,5 @@
+-- Grant 'agents-access' to every user who has ever created a chat.
+UPDATE users
+SET rbac_roles = array_append(rbac_roles, 'agents-access')
+WHERE id IN (SELECT DISTINCT owner_id FROM chats)
+  AND NOT ('agents-access' = ANY(rbac_roles));

coderd/database/migrations/000458_automations.down.sql

@@ -0,0 +1,13 @@
+ALTER TABLE chats DROP COLUMN IF EXISTS automation_id;
+
+DROP TABLE IF EXISTS chat_automation_events;
+
+DROP TABLE IF EXISTS chat_automation_triggers;
+
+DROP TABLE IF EXISTS chat_automations;
+
+DROP TYPE IF EXISTS chat_automation_event_status;
+
+DROP TYPE IF EXISTS chat_automation_trigger_type;
+
+DROP TYPE IF EXISTS chat_automation_status;

coderd/database/migrations/000458_automations.up.sql

@@ -0,0 +1,238 @@
+-- Chat automations bridge external events (webhooks, cron schedules) to
+-- Coder chats. A chat automation defines *what* to say, *which* model
+-- and tools to use, and *how fast* it is allowed to create or continue
+-- chats.
+
+CREATE TYPE chat_automation_status AS ENUM ('disabled', 'preview', 'active');
+CREATE TYPE chat_automation_trigger_type AS ENUM ('webhook', 'cron');
+CREATE TYPE chat_automation_event_status AS ENUM ('filtered', 'preview', 'created', 'continued', 'rate_limited', 'error');
+
+CREATE TABLE chat_automations (
+    id uuid NOT NULL,
+    -- The user on whose behalf chats are created. All RBAC checks and
+    -- chat ownership are scoped to this user.
+    owner_id uuid NOT NULL,
+    -- Organization scope for RBAC. Combined with owner_id and name to
+    -- form a unique constraint so automations are namespaced per user
+    -- per org.
+    organization_id uuid NOT NULL,
+    -- Human-readable identifier. Unique within (owner_id, organization_id).
+    name text NOT NULL,
+    -- Optional long-form description shown in the UI.
+    description text NOT NULL DEFAULT '',
+    -- The user-role message injected into every chat this automation
+    -- creates. This is the core prompt that tells the LLM what to do.
+    instructions text NOT NULL DEFAULT '',
+    -- Optional model configuration override. When NULL the deployment
+    -- default is used. SET NULL on delete so automations survive config
+    -- changes gracefully.
+    model_config_id uuid,
+    -- MCP servers to attach to chats created by this automation.
+    -- Stored as an array of UUIDs rather than a join table because
+    -- the set is small and always read/written atomically.
+    mcp_server_ids uuid[] NOT NULL DEFAULT '{}',
+    -- Tool allowlist. Empty means all tools available to the model
+    -- config are permitted.
+    allowed_tools text[] NOT NULL DEFAULT '{}',
+    -- Lifecycle state:
+    --   disabled — trigger events are silently dropped.
+    --   preview  — events are logged but no chat is created (dry-run).
+    --   active   — events create or continue chats.
+    status chat_automation_status NOT NULL DEFAULT 'disabled',
+    -- Maximum number of *new* chats this automation may create in a
+    -- rolling one-hour window. Prevents runaway webhook storms from
+    -- flooding the system. Approximate under concurrency; the
+    -- check-then-insert is not serialized, so brief bursts may
+    -- slightly exceed the cap.
+    max_chat_creates_per_hour integer NOT NULL DEFAULT 10,
+    -- Maximum total messages (creates + continues) this automation may
+    -- send in a rolling one-hour window. A second, broader throttle
+    -- that catches high-frequency continuation patterns. Same
+    -- approximate-under-concurrency caveat as above.
+    max_messages_per_hour integer NOT NULL DEFAULT 60,
+    created_at timestamp with time zone NOT NULL,
+    updated_at timestamp with time zone NOT NULL,
+    PRIMARY KEY (id),
+    FOREIGN KEY (owner_id) REFERENCES users(id) ON DELETE CASCADE,
+    FOREIGN KEY (organization_id) REFERENCES organizations(id) ON DELETE CASCADE,
+    FOREIGN KEY (model_config_id) REFERENCES chat_model_configs(id) ON DELETE SET NULL,
+    CONSTRAINT chat_automations_max_chat_creates_per_hour_check CHECK (max_chat_creates_per_hour > 0),
+    CONSTRAINT chat_automations_max_messages_per_hour_check CHECK (max_messages_per_hour > 0)
+);
+
+CREATE INDEX idx_chat_automations_owner_id ON chat_automations (owner_id);
+CREATE INDEX idx_chat_automations_organization_id ON chat_automations (organization_id);
+
+-- Enforces that automation names are unique per user per org so they
+-- can be referenced unambiguously in CLI/API calls.
+CREATE UNIQUE INDEX idx_chat_automations_owner_org_name ON chat_automations (owner_id, organization_id, name);
+
+-- Triggers define *how* an automation is invoked. Each automation can
+-- have multiple triggers (e.g. one webhook + one cron schedule).
+-- Webhook and cron triggers share the same row shape with type-specific
+-- nullable columns to keep the schema simple.
+CREATE TABLE chat_automation_triggers (
+    id uuid NOT NULL,
+    -- Parent automation. CASCADE delete ensures orphan triggers are
+    -- cleaned up when an automation is removed.
+    automation_id uuid NOT NULL,
+    -- Discriminator: 'webhook' or 'cron'. Determines which nullable
+    -- columns are meaningful.
+    type chat_automation_trigger_type NOT NULL,
+    -- HMAC-SHA256 shared secret for webhook signature verification
+    -- (X-Hub-Signature-256 header). NULL for cron triggers.
+    webhook_secret text,
+    -- Identifier of the dbcrypt key used to encrypt webhook_secret.
+    -- NULL means the secret is not yet encrypted. When dbcrypt is
+    -- enabled, this references the active key digest used for
+    -- AES-256-GCM encryption.
+    webhook_secret_key_id text REFERENCES dbcrypt_keys(active_key_digest),
+    -- Standard 5-field cron expression (minute hour dom month dow),
+    -- with optional CRON_TZ= prefix. NULL for webhook triggers.
+    cron_schedule text,
+    -- Timestamp of the last successful cron fire. The scheduler
+    -- computes next = cron.Next(last_triggered_at) and fires when
+    -- next <= now. NULL means the trigger has never fired; the
+    -- scheduler falls back to created_at as the reference time.
+    -- Not used for webhook triggers.
+    last_triggered_at timestamp with time zone,
+    -- gjson path→value filter conditions evaluated against the
+    -- incoming webhook payload. All conditions must match for the
+    -- trigger to fire. NULL or empty means "match everything".
+    filter jsonb,
+    -- Maps chat label keys to gjson paths. When a trigger fires,
+    -- labels are resolved from the payload and used to find an
+    -- existing chat to continue (by label match) or set on a
+    -- newly created chat. This is how automations route events
+    -- to the right conversation.
+    label_paths jsonb,
+    created_at timestamp with time zone NOT NULL,
+    updated_at timestamp with time zone NOT NULL,
+    PRIMARY KEY (id),
+    FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE,
+    CONSTRAINT chat_automation_triggers_webhook_fields CHECK (
+        type != 'webhook' OR (webhook_secret IS NOT NULL AND cron_schedule IS NULL AND last_triggered_at IS NULL)
+    ),
+    CONSTRAINT chat_automation_triggers_cron_fields CHECK (
+        type != 'cron' OR (cron_schedule IS NOT NULL AND webhook_secret IS NULL AND webhook_secret_key_id IS NULL)
+    )
+);
+
+CREATE INDEX idx_chat_automation_triggers_automation_id ON chat_automation_triggers (automation_id);
+
+-- Every trigger invocation produces an event row regardless of outcome.
+-- This table is the audit trail and the data source for rate-limit
+-- window counts. Rows are append-only and expected to be purged by a
+-- background job after a retention period.
+CREATE TABLE chat_automation_events (
+    id uuid NOT NULL,
+    -- The automation that owns this event.
+    automation_id uuid NOT NULL,
+    -- The trigger that produced this event. SET NULL on delete so
+    -- historical events survive trigger removal.
+    trigger_id uuid,
+    -- When the event was received (webhook delivery time or cron
+    -- evaluation time). Used for rate-limit window calculations and
+    -- purge cutoffs.
+    received_at timestamp with time zone NOT NULL,
+    -- The raw payload that was evaluated. For webhooks this is the
+    -- HTTP body; for cron triggers it is a synthetic JSON envelope
+    -- with schedule metadata.
+    payload jsonb NOT NULL,
+    -- Whether the trigger's filter conditions matched. False means
+    -- the event was dropped before any chat interaction.
+    filter_matched boolean NOT NULL,
+    -- Labels resolved from the payload via label_paths. Stored so
+    -- the event log shows exactly which labels were computed.
+    resolved_labels jsonb,
+    -- ID of an existing chat that was found via label matching and
+    -- continued with a new message.
+    matched_chat_id uuid,
+    -- ID of a newly created chat (mutually exclusive with
+    -- matched_chat_id in practice).
+    created_chat_id uuid,
+    -- Outcome of the event:
+    --   filtered     — filter did not match, event dropped.
+    --   preview      — automation is in preview mode, no chat action.
+    --   created      — new chat was created.
+    --   continued    — existing chat was continued.
+    --   rate_limited — rate limit prevented chat action.
+    --   error        — something went wrong (see error column).
+    status chat_automation_event_status NOT NULL,
+    -- Human-readable error description when status = 'error' or
+    -- 'rate_limited'. NULL for successful outcomes.
+    error text,
+    PRIMARY KEY (id),
+    FOREIGN KEY (automation_id) REFERENCES chat_automations(id) ON DELETE CASCADE,
+    FOREIGN KEY (trigger_id) REFERENCES chat_automation_triggers(id) ON DELETE SET NULL,
+    FOREIGN KEY (matched_chat_id) REFERENCES chats(id) ON DELETE SET NULL,
+    FOREIGN KEY (created_chat_id) REFERENCES chats(id) ON DELETE SET NULL,
+    CONSTRAINT chat_automation_events_chat_exclusivity CHECK (
+        matched_chat_id IS NULL OR created_chat_id IS NULL
+    )
+);
+
+-- Composite index for listing events per automation in reverse
+-- chronological order (the primary UI query pattern).
+CREATE INDEX idx_chat_automation_events_automation_id_received_at ON chat_automation_events (automation_id, received_at DESC);
+
+-- Standalone index on received_at for the purge job, which deletes
+-- events older than the retention period across all automations.
+CREATE INDEX idx_chat_automation_events_received_at ON chat_automation_events (received_at);
+
+-- Partial index for rate-limit window count queries, which filter
+-- by automation_id and status IN ('created', 'continued').
+CREATE INDEX idx_chat_automation_events_rate_limit
+  ON chat_automation_events (automation_id, received_at)
+  WHERE status IN ('created', 'continued');
+
+-- Link chats back to the automation that created them. SET NULL on
+-- delete so chats survive if the automation is removed. Indexed for
+-- lookup queries that list chats spawned by a given automation.
+ALTER TABLE chats ADD COLUMN automation_id uuid REFERENCES chat_automations(id) ON DELETE SET NULL;
+
+CREATE INDEX idx_chats_automation_id ON chats (automation_id);
+
+-- Enum type comments.
+COMMENT ON TYPE chat_automation_status IS 'Lifecycle state of a chat automation: disabled, preview, or active.';
+COMMENT ON TYPE chat_automation_trigger_type IS 'Discriminator for chat automation triggers: webhook or cron.';
+COMMENT ON TYPE chat_automation_event_status IS 'Outcome of a chat automation event: filtered, preview, created, continued, rate_limited, or error.';
+
+-- Table comments.
+COMMENT ON TABLE chat_automations IS 'Chat automations bridge external events (webhooks, cron schedules) to Coder chats. A chat automation defines what to say, which model and tools to use, and how fast it is allowed to create or continue chats.';
+COMMENT ON TABLE chat_automation_triggers IS 'Triggers define how an automation is invoked. Each automation can have multiple triggers (e.g. one webhook + one cron schedule). Webhook and cron triggers share the same row shape with type-specific nullable columns to keep the schema simple.';
+COMMENT ON TABLE chat_automation_events IS 'Every trigger invocation produces an event row regardless of outcome. This table is the audit trail and the data source for rate-limit window counts. Rows are append-only and expected to be purged by a background job after a retention period.';
+
+-- Column comments for chat_automations.
+COMMENT ON COLUMN chat_automations.owner_id IS 'The user on whose behalf chats are created. All RBAC checks and chat ownership are scoped to this user.';
+COMMENT ON COLUMN chat_automations.organization_id IS 'Organization scope for RBAC. Combined with owner_id and name to form a unique constraint so automations are namespaced per user per org.';
+COMMENT ON COLUMN chat_automations.instructions IS 'The user-role message injected into every chat this automation creates. This is the core prompt that tells the LLM what to do.';
+COMMENT ON COLUMN chat_automations.model_config_id IS 'Optional model configuration override. When NULL the deployment default is used. SET NULL on delete so automations survive config changes gracefully.';
+COMMENT ON COLUMN chat_automations.mcp_server_ids IS 'MCP servers to attach to chats created by this automation. Stored as an array of UUIDs rather than a join table because the set is small and always read/written atomically.';
+COMMENT ON COLUMN chat_automations.allowed_tools IS 'Tool allowlist. Empty means all tools available to the model config are permitted.';
+COMMENT ON COLUMN chat_automations.status IS 'Lifecycle state: disabled — trigger events are silently dropped; preview — events are logged but no chat is created (dry-run); active — events create or continue chats.';
+COMMENT ON COLUMN chat_automations.max_chat_creates_per_hour IS 'Maximum number of new chats this automation may create in a rolling one-hour window. Prevents runaway webhook storms from flooding the system.';
+COMMENT ON COLUMN chat_automations.max_messages_per_hour IS 'Maximum total messages (creates + continues) this automation may send in a rolling one-hour window. A second, broader throttle that catches high-frequency continuation patterns.';
+
+-- Column comments for chat_automation_triggers.
+COMMENT ON COLUMN chat_automation_triggers.type IS 'Discriminator: webhook or cron. Determines which nullable columns are meaningful.';
+COMMENT ON COLUMN chat_automation_triggers.webhook_secret IS 'HMAC-SHA256 shared secret for webhook signature verification (X-Hub-Signature-256 header). NULL for cron triggers.';
+COMMENT ON COLUMN chat_automation_triggers.cron_schedule IS 'Standard 5-field cron expression (minute hour dom month dow), with optional CRON_TZ= prefix. NULL for webhook triggers.';
+COMMENT ON COLUMN chat_automation_triggers.filter IS 'gjson path-to-value filter conditions evaluated against the incoming webhook payload. All conditions must match for the trigger to fire. NULL or empty means match everything.';
+COMMENT ON COLUMN chat_automation_triggers.label_paths IS 'Maps chat label keys to gjson paths. When a trigger fires, labels are resolved from the payload and used to find an existing chat to continue (by label match) or set on a newly created chat.';
+COMMENT ON COLUMN chat_automation_triggers.last_triggered_at IS 'Timestamp of the last successful cron fire. The scheduler computes next = cron.Next(last_triggered_at) and fires when next <= now. NULL means the trigger has never fired. Not used for webhook triggers.';
+
+-- Column comments for chat_automation_events.
+COMMENT ON COLUMN chat_automation_events.payload IS 'The raw payload that was evaluated. For webhooks this is the HTTP body; for cron triggers it is a synthetic JSON envelope with schedule metadata.';
+COMMENT ON COLUMN chat_automation_events.filter_matched IS 'Whether the trigger filter conditions matched. False means the event was dropped before any chat interaction.';
+COMMENT ON COLUMN chat_automation_events.resolved_labels IS 'Labels resolved from the payload via label_paths. Stored so the event log shows exactly which labels were computed.';
+COMMENT ON COLUMN chat_automation_events.matched_chat_id IS 'ID of an existing chat that was found via label matching and continued with a new message.';
+COMMENT ON COLUMN chat_automation_events.created_chat_id IS 'ID of a newly created chat (mutually exclusive with matched_chat_id in practice).';
+COMMENT ON COLUMN chat_automation_events.status IS 'Outcome of the event: filtered — filter did not match; preview — automation is in preview mode; created — new chat was created; continued — existing chat was continued; rate_limited — rate limit prevented chat action; error — something went wrong.';
+
+-- Add API key scope values for the new chat_automation resource type.
+ALTER TYPE api_key_scope ADD VALUE IF NOT EXISTS 'chat_automation:create';
+ALTER TYPE api_key_scope ADD VALUE IF NOT EXISTS 'chat_automation:read';
+ALTER TYPE api_key_scope ADD VALUE IF NOT EXISTS 'chat_automation:update';
+ALTER TYPE api_key_scope ADD VALUE IF NOT EXISTS 'chat_automation:delete';
+ALTER TYPE api_key_scope ADD VALUE IF NOT EXISTS 'chat_automation:*';

coderd/database/migrations/migrate_test.go

@@ -877,3 +877,149 @@ func TestMigration000387MigrateTaskWorkspaces(t *testing.T) {
 	require.NoError(t, err)
 	require.Equal(t, 0, antCount, "antagonist workspaces (deleted and regular) should not be migrated")
 }
+
+func TestMigration000457ChatAccessRole(t *testing.T) {
+	t.Parallel()
+
+	const migrationVersion = 457
+
+	sqlDB := testSQLDB(t)
+
+	// Migrate up to the migration before the one that grants
+	// agents-access roles.
+	next, err := migrations.Stepper(sqlDB)
+	require.NoError(t, err)
+	for {
+		version, more, err := next()
+		require.NoError(t, err)
+		if !more {
+			t.Fatalf("migration %d not found", migrationVersion)
+		}
+		if version == migrationVersion-1 {
+			break
+		}
+	}
+
+	ctx := testutil.Context(t, testutil.WaitSuperLong)
+
+	// Define test users.
+	userWithChat := uuid.New()         // Has a chat, no agents-access role.
+	userAlreadyHasRole := uuid.New()   // Has a chat and already has agents-access.
+	userNoChat := uuid.New()           // No chat at all.
+	userWithChatAndRoles := uuid.New() // Has a chat and other existing roles.
+
+	now := time.Now().UTC().Truncate(time.Microsecond)
+
+	// We need a chat_provider and chat_model_config for the chats FK.
+	providerID := uuid.New()
+	modelConfigID := uuid.New()
+
+	tx, err := sqlDB.BeginTx(ctx, nil)
+	require.NoError(t, err)
+	defer tx.Rollback()
+
+	fixtures := []struct {
+		query string
+		args  []any
+	}{
+		// Insert test users with varying rbac_roles.
+		{
+			`INSERT INTO users (id, username, email, hashed_password, created_at, updated_at, status, rbac_roles, login_type)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)`,
+			[]any{userWithChat, "user-with-chat", "chat@test.com", []byte{}, now, now, "active", pq.StringArray{}, "password"},
+		},
+		{
+			`INSERT INTO users (id, username, email, hashed_password, created_at, updated_at, status, rbac_roles, login_type)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)`,
+			[]any{userAlreadyHasRole, "user-already-has-role", "already@test.com", []byte{}, now, now, "active", pq.StringArray{"agents-access"}, "password"},
+		},
+		{
+			`INSERT INTO users (id, username, email, hashed_password, created_at, updated_at, status, rbac_roles, login_type)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)`,
+			[]any{userNoChat, "user-no-chat", "nochat@test.com", []byte{}, now, now, "active", pq.StringArray{}, "password"},
+		},
+		{
+			`INSERT INTO users (id, username, email, hashed_password, created_at, updated_at, status, rbac_roles, login_type)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)`,
+			[]any{userWithChatAndRoles, "user-with-roles", "roles@test.com", []byte{}, now, now, "active", pq.StringArray{"template-admin"}, "password"},
+		},
+		// Insert a chat provider and model config for the chats FK.
+		{
+			`INSERT INTO chat_providers (id, provider, display_name, api_key, enabled, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6, $7)`,
+			[]any{providerID, "openai", "OpenAI", "", true, now, now},
+		},
+		{
+			`INSERT INTO chat_model_configs (id, provider, model, display_name, enabled, context_limit, compression_threshold, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9)`,
+			[]any{modelConfigID, "openai", "gpt-4", "GPT 4", true, 100000, 70, now, now},
+		},
+		// Insert chats for users A, B, and D (not C).
+		{
+			`INSERT INTO chats (id, owner_id, last_model_config_id, title, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6)`,
+			[]any{uuid.New(), userWithChat, modelConfigID, "Chat A", now, now},
+		},
+		{
+			`INSERT INTO chats (id, owner_id, last_model_config_id, title, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6)`,
+			[]any{uuid.New(), userAlreadyHasRole, modelConfigID, "Chat B", now, now},
+		},
+		{
+			`INSERT INTO chats (id, owner_id, last_model_config_id, title, created_at, updated_at)
+			VALUES ($1, $2, $3, $4, $5, $6)`,
+			[]any{uuid.New(), userWithChatAndRoles, modelConfigID, "Chat D", now, now},
+		},
+	}
+
+	for i, f := range fixtures {
+		_, err := tx.ExecContext(ctx, f.query, f.args...)
+		require.NoError(t, err, "fixture %d", i)
+	}
+	require.NoError(t, tx.Commit())
+
+	// Run the migration.
+	version, _, err := next()
+	require.NoError(t, err)
+	require.EqualValues(t, migrationVersion, version)
+
+	// Helper to get rbac_roles for a user.
+	getRoles := func(t *testing.T, userID uuid.UUID) []string {
+		t.Helper()
+		var roles pq.StringArray
+		err := sqlDB.QueryRowContext(ctx,
+			"SELECT rbac_roles FROM users WHERE id = $1", userID,
+		).Scan(&roles)
+		require.NoError(t, err)
+		return roles
+	}
+
+	// Verify: user with chat gets agents-access.
+	roles := getRoles(t, userWithChat)
+	require.Contains(t, roles, "agents-access",
+		"user with chat should get agents-access")
+
+	// Verify: user who already had agents-access has no duplicate.
+	roles = getRoles(t, userAlreadyHasRole)
+	count := 0
+	for _, r := range roles {
+		if r == "agents-access" {
+			count++
+		}
+	}
+	require.Equal(t, 1, count,
+		"user who already had agents-access should not get a duplicate")
+
+	// Verify: user without chat does NOT get agents-access.
+	roles = getRoles(t, userNoChat)
+	require.NotContains(t, roles, "agents-access",
+		"user without chat should not get agents-access")
+
+	// Verify: user with chat and existing roles gets agents-access
+	// appended while preserving existing roles.
+	roles = getRoles(t, userWithChatAndRoles)
+	require.Contains(t, roles, "agents-access",
+		"user with chat and other roles should get agents-access")
+	require.Contains(t, roles, "template-admin",
+		"existing roles should be preserved")
+}

coderd/database/migrations/testdata/fixtures/000458_automations.up.sql

@@ -0,0 +1,87 @@
+INSERT INTO chat_automations (
+    id,
+    owner_id,
+    organization_id,
+    name,
+    description,
+    instructions,
+    model_config_id,
+    mcp_server_ids,
+    allowed_tools,
+    status,
+    max_chat_creates_per_hour,
+    max_messages_per_hour,
+    created_at,
+    updated_at
+)
+SELECT
+    'b3d0fd0e-8e1a-4f2c-9a3b-1234567890ab',
+    u.id,
+    o.id,
+    'fixture-automation',
+    'Fixture automation for migration testing.',
+    'You are a helpful assistant.',
+    NULL,
+    '{}',
+    '{}',
+    'active',
+    10,
+    60,
+    '2024-01-01 00:00:00+00',
+    '2024-01-01 00:00:00+00'
+FROM users u
+CROSS JOIN organizations o
+ORDER BY u.created_at, u.id
+LIMIT 1;
+
+INSERT INTO chat_automation_triggers (
+    id,
+    automation_id,
+    type,
+    webhook_secret,
+    webhook_secret_key_id,
+    cron_schedule,
+    last_triggered_at,
+    filter,
+    label_paths,
+    created_at,
+    updated_at
+) VALUES (
+    'c4e1fe1f-9f2b-4a3d-ab4c-234567890abc',
+    'b3d0fd0e-8e1a-4f2c-9a3b-1234567890ab',
+    'webhook',
+    'whsec_fixture_secret',
+    NULL,
+    NULL,
+    NULL,
+    '{"action": "opened"}'::jsonb,
+    '{"repo": "repository.full_name"}'::jsonb,
+    '2024-01-01 00:00:00+00',
+    '2024-01-01 00:00:00+00'
+);
+
+INSERT INTO chat_automation_events (
+    id,
+    automation_id,
+    trigger_id,
+    received_at,
+    payload,
+    filter_matched,
+    resolved_labels,
+    matched_chat_id,
+    created_chat_id,
+    status,
+    error
+) VALUES (
+    'd5f20f20-a03c-4b4e-bc5d-345678901bcd',
+    'b3d0fd0e-8e1a-4f2c-9a3b-1234567890ab',
+    'c4e1fe1f-9f2b-4a3d-ab4c-234567890abc',
+    '2024-01-01 00:00:00+00',
+    '{"action": "opened", "repository": {"full_name": "coder/coder"}}'::jsonb,
+    TRUE,
+    '{"repo": "coder/coder"}'::jsonb,
+    NULL,
+    NULL,
+    'preview',
+    NULL
+);

coderd/database/modelmethods.go

@@ -182,6 +182,13 @@ func (r GetChatsRow) RBACObject() rbac.Object {
 	return r.Chat.RBACObject()
 }
 
+func (a ChatAutomation) RBACObject() rbac.Object {
+	return rbac.ResourceChatAutomation.
+		WithID(a.ID).
+		WithOwner(a.OwnerID.String()).
+		InOrg(a.OrganizationID)
+}
+
 func (c ChatFile) RBACObject() rbac.Object {
 	return rbac.ResourceChat.WithID(c.ID).WithOwner(c.OwnerID.String()).InOrg(c.OrganizationID)
 }

coderd/database/modelqueries.go

@@ -53,6 +53,7 @@ type customQuerier interface {
 	connectionLogQuerier
 	aibridgeQuerier
 	chatQuerier
+	chatAutomationQuerier
 }
 
 type templateQuerier interface {
@@ -795,7 +796,71 @@ func (q *sqlQuerier) GetAuthorizedChats(ctx context.Context, arg GetChatsParams,
 			&i.Chat.AgentID,
 			&i.Chat.PinOrder,
 			&i.Chat.LastReadMessageID,
-			&i.HasUnread); err != nil {
+			&i.Chat.LastInjectedContext,
+			&i.Chat.AutomationID,
+			&i.HasUnread,
+		); err != nil {
+			return nil, err
+		}
+		items = append(items, i)
+	}
+	if err := rows.Close(); err != nil {
+		return nil, err
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+type chatAutomationQuerier interface {
+	GetAuthorizedChatAutomations(ctx context.Context, arg GetChatAutomationsParams, prepared rbac.PreparedAuthorized) ([]ChatAutomation, error)
+}
+
+func (q *sqlQuerier) GetAuthorizedChatAutomations(ctx context.Context, arg GetChatAutomationsParams, prepared rbac.PreparedAuthorized) ([]ChatAutomation, error) {
+	authorizedFilter, err := prepared.CompileToSQL(ctx, regosql.ConvertConfig{
+		VariableConverter: regosql.NoACLConverter(),
+	})
+	if err != nil {
+		return nil, xerrors.Errorf("compile authorized filter: %w", err)
+	}
+
+	filtered, err := insertAuthorizedFilter(getChatAutomations, fmt.Sprintf(" AND %s", authorizedFilter))
+	if err != nil {
+		return nil, xerrors.Errorf("insert authorized filter: %w", err)
+	}
+
+	// The name comment is for metric tracking
+	query := fmt.Sprintf("-- name: GetAuthorizedChatAutomations :many\n%s", filtered)
+	rows, err := q.db.QueryContext(ctx, query,
+		arg.OwnerID,
+		arg.OrganizationID,
+		arg.OffsetOpt,
+		arg.LimitOpt,
+	)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []ChatAutomation
+	for rows.Next() {
+		var i ChatAutomation
+		if err := rows.Scan(
+			&i.ID,
+			&i.OwnerID,
+			&i.OrganizationID,
+			&i.Name,
+			&i.Description,
+			&i.Instructions,
+			&i.ModelConfigID,
+			pq.Array(&i.MCPServerIDs),
+			pq.Array(&i.AllowedTools),
+			&i.Status,
+			&i.MaxChatCreatesPerHour,
+			&i.MaxMessagesPerHour,
+			&i.CreatedAt,
+			&i.UpdatedAt,
+		); err != nil {
 			return nil, err
 		}
 		items = append(items, i)
@@ -995,8 +1060,6 @@ func (q *sqlQuerier) ListAuthorizedAIBridgeSessions(ctx context.Context, arg Lis
 	query := fmt.Sprintf("-- name: ListAuthorizedAIBridgeSessions :many\n%s", filtered)
 	rows, err := q.db.QueryContext(ctx, query,
 		arg.AfterSessionID,
-		arg.Offset,
-		arg.Limit,
 		arg.StartedAfter,
 		arg.StartedBefore,
 		arg.InitiatorID,
@@ -1004,6 +1067,8 @@ func (q *sqlQuerier) ListAuthorizedAIBridgeSessions(ctx context.Context, arg Lis
 		arg.Model,
 		arg.Client,
 		arg.SessionID,
+		arg.Offset,
+		arg.Limit,
 	)
 	if err != nil {
 		return nil, err

coderd/database/models.go

@@ -224,6 +224,11 @@ const (
 	ApiKeyScopeChatUpdate                          APIKeyScope = "chat:update"
 	ApiKeyScopeChatDelete                          APIKeyScope = "chat:delete"
 	ApiKeyScopeChat                                APIKeyScope = "chat:*"
+	ApiKeyScopeChatAutomationCreate                APIKeyScope = "chat_automation:create"
+	ApiKeyScopeChatAutomationRead                  APIKeyScope = "chat_automation:read"
+	ApiKeyScopeChatAutomationUpdate                APIKeyScope = "chat_automation:update"
+	ApiKeyScopeChatAutomationDelete                APIKeyScope = "chat_automation:delete"
+	ApiKeyScopeChatAutomation                      APIKeyScope = "chat_automation:*"
 )
 
 func (e *APIKeyScope) Scan(src interface{}) error {
@@ -467,7 +472,12 @@ func (e APIKeyScope) Valid() bool {
 		ApiKeyScopeChatRead,
 		ApiKeyScopeChatUpdate,
 		ApiKeyScopeChatDelete,
-		ApiKeyScopeChat:
+		ApiKeyScopeChat,
+		ApiKeyScopeChatAutomationCreate,
+		ApiKeyScopeChatAutomationRead,
+		ApiKeyScopeChatAutomationUpdate,
+		ApiKeyScopeChatAutomationDelete,
+		ApiKeyScopeChatAutomation:
 		return true
 	}
 	return false
@@ -680,6 +690,11 @@ func AllAPIKeyScopeValues() []APIKeyScope {
 		ApiKeyScopeChatUpdate,
 		ApiKeyScopeChatDelete,
 		ApiKeyScopeChat,
+		ApiKeyScopeChatAutomationCreate,
+		ApiKeyScopeChatAutomationRead,
+		ApiKeyScopeChatAutomationUpdate,
+		ApiKeyScopeChatAutomationDelete,
+		ApiKeyScopeChatAutomation,
 	}
 }
 
@@ -1107,6 +1122,198 @@ func AllBuildReasonValues() []BuildReason {
 	}
 }
 
+// Outcome of a chat automation event: filtered, preview, created, continued, rate_limited, or error.
+type ChatAutomationEventStatus string
+
+const (
+	ChatAutomationEventStatusFiltered    ChatAutomationEventStatus = "filtered"
+	ChatAutomationEventStatusPreview     ChatAutomationEventStatus = "preview"
+	ChatAutomationEventStatusCreated     ChatAutomationEventStatus = "created"
+	ChatAutomationEventStatusContinued   ChatAutomationEventStatus = "continued"
+	ChatAutomationEventStatusRateLimited ChatAutomationEventStatus = "rate_limited"
+	ChatAutomationEventStatusError       ChatAutomationEventStatus = "error"
+)
+
+func (e *ChatAutomationEventStatus) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = ChatAutomationEventStatus(s)
+	case string:
+		*e = ChatAutomationEventStatus(s)
+	default:
+		return fmt.Errorf("unsupported scan type for ChatAutomationEventStatus: %T", src)
+	}
+	return nil
+}
+
+type NullChatAutomationEventStatus struct {
+	ChatAutomationEventStatus ChatAutomationEventStatus `json:"chat_automation_event_status"`
+	Valid                     bool                      `json:"valid"` // Valid is true if ChatAutomationEventStatus is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullChatAutomationEventStatus) Scan(value interface{}) error {
+	if value == nil {
+		ns.ChatAutomationEventStatus, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.ChatAutomationEventStatus.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullChatAutomationEventStatus) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.ChatAutomationEventStatus), nil
+}
+
+func (e ChatAutomationEventStatus) Valid() bool {
+	switch e {
+	case ChatAutomationEventStatusFiltered,
+		ChatAutomationEventStatusPreview,
+		ChatAutomationEventStatusCreated,
+		ChatAutomationEventStatusContinued,
+		ChatAutomationEventStatusRateLimited,
+		ChatAutomationEventStatusError:
+		return true
+	}
+	return false
+}
+
+func AllChatAutomationEventStatusValues() []ChatAutomationEventStatus {
+	return []ChatAutomationEventStatus{
+		ChatAutomationEventStatusFiltered,
+		ChatAutomationEventStatusPreview,
+		ChatAutomationEventStatusCreated,
+		ChatAutomationEventStatusContinued,
+		ChatAutomationEventStatusRateLimited,
+		ChatAutomationEventStatusError,
+	}
+}
+
+// Lifecycle state of a chat automation: disabled, preview, or active.
+type ChatAutomationStatus string
+
+const (
+	ChatAutomationStatusDisabled ChatAutomationStatus = "disabled"
+	ChatAutomationStatusPreview  ChatAutomationStatus = "preview"
+	ChatAutomationStatusActive   ChatAutomationStatus = "active"
+)
+
+func (e *ChatAutomationStatus) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = ChatAutomationStatus(s)
+	case string:
+		*e = ChatAutomationStatus(s)
+	default:
+		return fmt.Errorf("unsupported scan type for ChatAutomationStatus: %T", src)
+	}
+	return nil
+}
+
+type NullChatAutomationStatus struct {
+	ChatAutomationStatus ChatAutomationStatus `json:"chat_automation_status"`
+	Valid                bool                 `json:"valid"` // Valid is true if ChatAutomationStatus is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullChatAutomationStatus) Scan(value interface{}) error {
+	if value == nil {
+		ns.ChatAutomationStatus, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.ChatAutomationStatus.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullChatAutomationStatus) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.ChatAutomationStatus), nil
+}
+
+func (e ChatAutomationStatus) Valid() bool {
+	switch e {
+	case ChatAutomationStatusDisabled,
+		ChatAutomationStatusPreview,
+		ChatAutomationStatusActive:
+		return true
+	}
+	return false
+}
+
+func AllChatAutomationStatusValues() []ChatAutomationStatus {
+	return []ChatAutomationStatus{
+		ChatAutomationStatusDisabled,
+		ChatAutomationStatusPreview,
+		ChatAutomationStatusActive,
+	}
+}
+
+// Discriminator for chat automation triggers: webhook or cron.
+type ChatAutomationTriggerType string
+
+const (
+	ChatAutomationTriggerTypeWebhook ChatAutomationTriggerType = "webhook"
+	ChatAutomationTriggerTypeCron    ChatAutomationTriggerType = "cron"
+)
+
+func (e *ChatAutomationTriggerType) Scan(src interface{}) error {
+	switch s := src.(type) {
+	case []byte:
+		*e = ChatAutomationTriggerType(s)
+	case string:
+		*e = ChatAutomationTriggerType(s)
+	default:
+		return fmt.Errorf("unsupported scan type for ChatAutomationTriggerType: %T", src)
+	}
+	return nil
+}
+
+type NullChatAutomationTriggerType struct {
+	ChatAutomationTriggerType ChatAutomationTriggerType `json:"chat_automation_trigger_type"`
+	Valid                     bool                      `json:"valid"` // Valid is true if ChatAutomationTriggerType is not NULL
+}
+
+// Scan implements the Scanner interface.
+func (ns *NullChatAutomationTriggerType) Scan(value interface{}) error {
+	if value == nil {
+		ns.ChatAutomationTriggerType, ns.Valid = "", false
+		return nil
+	}
+	ns.Valid = true
+	return ns.ChatAutomationTriggerType.Scan(value)
+}
+
+// Value implements the driver Valuer interface.
+func (ns NullChatAutomationTriggerType) Value() (driver.Value, error) {
+	if !ns.Valid {
+		return nil, nil
+	}
+	return string(ns.ChatAutomationTriggerType), nil
+}
+
+func (e ChatAutomationTriggerType) Valid() bool {
+	switch e {
+	case ChatAutomationTriggerTypeWebhook,
+		ChatAutomationTriggerTypeCron:
+		return true
+	}
+	return false
+}
+
+func AllChatAutomationTriggerTypeValues() []ChatAutomationTriggerType {
+	return []ChatAutomationTriggerType{
+		ChatAutomationTriggerTypeWebhook,
+		ChatAutomationTriggerTypeCron,
+	}
+}
+
 type ChatMessageRole string
 
 const (
@@ -4153,28 +4360,99 @@ type BoundaryUsageStat struct {
 }
 
 type Chat struct {
-	ID                uuid.UUID      `db:"id" json:"id"`
-	OwnerID           uuid.UUID      `db:"owner_id" json:"owner_id"`
-	WorkspaceID       uuid.NullUUID  `db:"workspace_id" json:"workspace_id"`
-	Title             string         `db:"title" json:"title"`
-	Status            ChatStatus     `db:"status" json:"status"`
-	WorkerID          uuid.NullUUID  `db:"worker_id" json:"worker_id"`
-	StartedAt         sql.NullTime   `db:"started_at" json:"started_at"`
-	HeartbeatAt       sql.NullTime   `db:"heartbeat_at" json:"heartbeat_at"`
-	CreatedAt         time.Time      `db:"created_at" json:"created_at"`
-	UpdatedAt         time.Time      `db:"updated_at" json:"updated_at"`
-	ParentChatID      uuid.NullUUID  `db:"parent_chat_id" json:"parent_chat_id"`
-	RootChatID        uuid.NullUUID  `db:"root_chat_id" json:"root_chat_id"`
-	LastModelConfigID uuid.UUID      `db:"last_model_config_id" json:"last_model_config_id"`
-	Archived          bool           `db:"archived" json:"archived"`
-	LastError         sql.NullString `db:"last_error" json:"last_error"`
-	Mode              NullChatMode   `db:"mode" json:"mode"`
-	MCPServerIDs      []uuid.UUID    `db:"mcp_server_ids" json:"mcp_server_ids"`
-	Labels            StringMap      `db:"labels" json:"labels"`
-	BuildID           uuid.NullUUID  `db:"build_id" json:"build_id"`
-	AgentID           uuid.NullUUID  `db:"agent_id" json:"agent_id"`
-	PinOrder          int32          `db:"pin_order" json:"pin_order"`
-	LastReadMessageID sql.NullInt64  `db:"last_read_message_id" json:"last_read_message_id"`
+	ID                  uuid.UUID             `db:"id" json:"id"`
+	OwnerID             uuid.UUID             `db:"owner_id" json:"owner_id"`
+	WorkspaceID         uuid.NullUUID         `db:"workspace_id" json:"workspace_id"`
+	Title               string                `db:"title" json:"title"`
+	Status              ChatStatus            `db:"status" json:"status"`
+	WorkerID            uuid.NullUUID         `db:"worker_id" json:"worker_id"`
+	StartedAt           sql.NullTime          `db:"started_at" json:"started_at"`
+	HeartbeatAt         sql.NullTime          `db:"heartbeat_at" json:"heartbeat_at"`
+	CreatedAt           time.Time             `db:"created_at" json:"created_at"`
+	UpdatedAt           time.Time             `db:"updated_at" json:"updated_at"`
+	ParentChatID        uuid.NullUUID         `db:"parent_chat_id" json:"parent_chat_id"`
+	RootChatID          uuid.NullUUID         `db:"root_chat_id" json:"root_chat_id"`
+	LastModelConfigID   uuid.UUID             `db:"last_model_config_id" json:"last_model_config_id"`
+	Archived            bool                  `db:"archived" json:"archived"`
+	LastError           sql.NullString        `db:"last_error" json:"last_error"`
+	Mode                NullChatMode          `db:"mode" json:"mode"`
+	MCPServerIDs        []uuid.UUID           `db:"mcp_server_ids" json:"mcp_server_ids"`
+	Labels              StringMap             `db:"labels" json:"labels"`
+	BuildID             uuid.NullUUID         `db:"build_id" json:"build_id"`
+	AgentID             uuid.NullUUID         `db:"agent_id" json:"agent_id"`
+	PinOrder            int32                 `db:"pin_order" json:"pin_order"`
+	LastReadMessageID   sql.NullInt64         `db:"last_read_message_id" json:"last_read_message_id"`
+	LastInjectedContext pqtype.NullRawMessage `db:"last_injected_context" json:"last_injected_context"`
+	AutomationID        uuid.NullUUID         `db:"automation_id" json:"automation_id"`
+}
+
+// Chat automations bridge external events (webhooks, cron schedules) to Coder chats. A chat automation defines what to say, which model and tools to use, and how fast it is allowed to create or continue chats.
+type ChatAutomation struct {
+	ID uuid.UUID `db:"id" json:"id"`
+	// The user on whose behalf chats are created. All RBAC checks and chat ownership are scoped to this user.
+	OwnerID uuid.UUID `db:"owner_id" json:"owner_id"`
+	// Organization scope for RBAC. Combined with owner_id and name to form a unique constraint so automations are namespaced per user per org.
+	OrganizationID uuid.UUID `db:"organization_id" json:"organization_id"`
+	Name           string    `db:"name" json:"name"`
+	Description    string    `db:"description" json:"description"`
+	// The user-role message injected into every chat this automation creates. This is the core prompt that tells the LLM what to do.
+	Instructions string `db:"instructions" json:"instructions"`
+	// Optional model configuration override. When NULL the deployment default is used. SET NULL on delete so automations survive config changes gracefully.
+	ModelConfigID uuid.NullUUID `db:"model_config_id" json:"model_config_id"`
+	// MCP servers to attach to chats created by this automation. Stored as an array of UUIDs rather than a join table because the set is small and always read/written atomically.
+	MCPServerIDs []uuid.UUID `db:"mcp_server_ids" json:"mcp_server_ids"`
+	// Tool allowlist. Empty means all tools available to the model config are permitted.
+	AllowedTools []string `db:"allowed_tools" json:"allowed_tools"`
+	// Lifecycle state: disabled — trigger events are silently dropped; preview — events are logged but no chat is created (dry-run); active — events create or continue chats.
+	Status ChatAutomationStatus `db:"status" json:"status"`
+	// Maximum number of new chats this automation may create in a rolling one-hour window. Prevents runaway webhook storms from flooding the system.
+	MaxChatCreatesPerHour int32 `db:"max_chat_creates_per_hour" json:"max_chat_creates_per_hour"`
+	// Maximum total messages (creates + continues) this automation may send in a rolling one-hour window. A second, broader throttle that catches high-frequency continuation patterns.
+	MaxMessagesPerHour int32     `db:"max_messages_per_hour" json:"max_messages_per_hour"`
+	CreatedAt          time.Time `db:"created_at" json:"created_at"`
+	UpdatedAt          time.Time `db:"updated_at" json:"updated_at"`
+}
+
+// Every trigger invocation produces an event row regardless of outcome. This table is the audit trail and the data source for rate-limit window counts. Rows are append-only and expected to be purged by a background job after a retention period.
+type ChatAutomationEvent struct {
+	ID           uuid.UUID     `db:"id" json:"id"`
+	AutomationID uuid.UUID     `db:"automation_id" json:"automation_id"`
+	TriggerID    uuid.NullUUID `db:"trigger_id" json:"trigger_id"`
+	ReceivedAt   time.Time     `db:"received_at" json:"received_at"`
+	// The raw payload that was evaluated. For webhooks this is the HTTP body; for cron triggers it is a synthetic JSON envelope with schedule metadata.
+	Payload json.RawMessage `db:"payload" json:"payload"`
+	// Whether the trigger filter conditions matched. False means the event was dropped before any chat interaction.
+	FilterMatched bool `db:"filter_matched" json:"filter_matched"`
+	// Labels resolved from the payload via label_paths. Stored so the event log shows exactly which labels were computed.
+	ResolvedLabels pqtype.NullRawMessage `db:"resolved_labels" json:"resolved_labels"`
+	// ID of an existing chat that was found via label matching and continued with a new message.
+	MatchedChatID uuid.NullUUID `db:"matched_chat_id" json:"matched_chat_id"`
+	// ID of a newly created chat (mutually exclusive with matched_chat_id in practice).
+	CreatedChatID uuid.NullUUID `db:"created_chat_id" json:"created_chat_id"`
+	// Outcome of the event: filtered — filter did not match; preview — automation is in preview mode; created — new chat was created; continued — existing chat was continued; rate_limited — rate limit prevented chat action; error — something went wrong.
+	Status ChatAutomationEventStatus `db:"status" json:"status"`
+	Error  sql.NullString            `db:"error" json:"error"`
+}
+
+// Triggers define how an automation is invoked. Each automation can have multiple triggers (e.g. one webhook + one cron schedule). Webhook and cron triggers share the same row shape with type-specific nullable columns to keep the schema simple.
+type ChatAutomationTrigger struct {
+	ID           uuid.UUID `db:"id" json:"id"`
+	AutomationID uuid.UUID `db:"automation_id" json:"automation_id"`
+	// Discriminator: webhook or cron. Determines which nullable columns are meaningful.
+	Type ChatAutomationTriggerType `db:"type" json:"type"`
+	// HMAC-SHA256 shared secret for webhook signature verification (X-Hub-Signature-256 header). NULL for cron triggers.
+	WebhookSecret      sql.NullString `db:"webhook_secret" json:"webhook_secret"`
+	WebhookSecretKeyID sql.NullString `db:"webhook_secret_key_id" json:"webhook_secret_key_id"`
+	// Standard 5-field cron expression (minute hour dom month dow), with optional CRON_TZ= prefix. NULL for webhook triggers.
+	CronSchedule sql.NullString `db:"cron_schedule" json:"cron_schedule"`
+	// Timestamp of the last successful cron fire. The scheduler computes next = cron.Next(last_triggered_at) and fires when next <= now. NULL means the trigger has never fired. Not used for webhook triggers.
+	LastTriggeredAt sql.NullTime `db:"last_triggered_at" json:"last_triggered_at"`
+	// gjson path-to-value filter conditions evaluated against the incoming webhook payload. All conditions must match for the trigger to fire. NULL or empty means match everything.
+	Filter pqtype.NullRawMessage `db:"filter" json:"filter"`
+	// Maps chat label keys to gjson paths. When a trigger fires, labels are resolved from the payload and used to find an existing chat to continue (by label match) or set on a newly created chat.
+	LabelPaths pqtype.NullRawMessage `db:"label_paths" json:"label_paths"`
+	CreatedAt  time.Time             `db:"created_at" json:"created_at"`
+	UpdatedAt  time.Time             `db:"updated_at" json:"updated_at"`
 }
 
 type ChatDiffStatus struct {

coderd/database/querier.go

@@ -54,7 +54,7 @@ type sqlcQuerier interface {
 	ActivityBumpWorkspace(ctx context.Context, arg ActivityBumpWorkspaceParams) error
 	// AllUserIDs returns all UserIDs regardless of user status or deletion.
 	AllUserIDs(ctx context.Context, includeSystem bool) ([]uuid.UUID, error)
-	ArchiveChatByID(ctx context.Context, id uuid.UUID) error
+	ArchiveChatByID(ctx context.Context, id uuid.UUID) ([]Chat, error)
 	// Archiving templates is a soft delete action, so is reversible.
 	// Archiving prevents the version from being used and discovered
 	// by listing.
@@ -74,10 +74,21 @@ type sqlcQuerier interface {
 	CleanTailnetCoordinators(ctx context.Context) error
 	CleanTailnetLostPeers(ctx context.Context) error
 	CleanTailnetTunnels(ctx context.Context) error
+	CleanupDeletedMCPServerIDsFromChatAutomations(ctx context.Context) error
 	CleanupDeletedMCPServerIDsFromChats(ctx context.Context) error
 	CountAIBridgeInterceptions(ctx context.Context, arg CountAIBridgeInterceptionsParams) (int64, error)
 	CountAIBridgeSessions(ctx context.Context, arg CountAIBridgeSessionsParams) (int64, error)
 	CountAuditLogs(ctx context.Context, arg CountAuditLogsParams) (int64, error)
+	// Counts new-chat events in the rate-limit window. This count is
+	// approximate under concurrency: concurrent webhook handlers may
+	// each read the same count before any of them insert, so brief
+	// bursts can slightly exceed the configured cap.
+	CountChatAutomationChatCreatesInWindow(ctx context.Context, arg CountChatAutomationChatCreatesInWindowParams) (int64, error)
+	// Counts total message events (creates + continues) in the rate-limit
+	// window. This count is approximate under concurrency: concurrent
+	// webhook handlers may each read the same count before any of them
+	// insert, so brief bursts can slightly exceed the configured cap.
+	CountChatAutomationMessagesInWindow(ctx context.Context, arg CountChatAutomationMessagesInWindowParams) (int64, error)
 	CountConnectionLogs(ctx context.Context, arg CountConnectionLogsParams) (int64, error)
 	// Counts enabled, non-deleted model configs that lack both input and
 	// output pricing in their JSONB options.cost configuration.
@@ -100,6 +111,8 @@ type sqlcQuerier interface {
 	// be recreated.
 	DeleteAllWebpushSubscriptions(ctx context.Context) error
 	DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, userID uuid.UUID) error
+	DeleteChatAutomationByID(ctx context.Context, id uuid.UUID) error
+	DeleteChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) error
 	DeleteChatModelConfigByID(ctx context.Context, id uuid.UUID) error
 	DeleteChatProviderByID(ctx context.Context, id uuid.UUID) error
 	DeleteChatQueuedMessage(ctx context.Context, arg DeleteChatQueuedMessageParams) error
@@ -197,6 +210,10 @@ type sqlcQuerier interface {
 	GetAPIKeysByUserID(ctx context.Context, arg GetAPIKeysByUserIDParams) ([]APIKey, error)
 	GetAPIKeysLastUsedAfter(ctx context.Context, lastUsed time.Time) ([]APIKey, error)
 	GetActiveAISeatCount(ctx context.Context) (int64, error)
+	// Returns all cron triggers whose parent automation is active or in
+	// preview mode. The scheduler uses this to evaluate which triggers
+	// are due.
+	GetActiveChatAutomationCronTriggers(ctx context.Context) ([]GetActiveChatAutomationCronTriggersRow, error)
 	GetActivePresetPrebuildSchedules(ctx context.Context) ([]TemplateVersionPresetPrebuildSchedule, error)
 	GetActiveUserCount(ctx context.Context, includeSystem bool) (int64, error)
 	GetActiveWorkspaceBuildsByTemplateID(ctx context.Context, templateID uuid.UUID) ([]WorkspaceBuild, error)
@@ -223,6 +240,11 @@ type sqlcQuerier interface {
 	// This function returns roles for authorization purposes. Implied member roles
 	// are included.
 	GetAuthorizationUserRoles(ctx context.Context, userID uuid.UUID) (GetAuthorizationUserRolesRow, error)
+	GetChatAutomationByID(ctx context.Context, id uuid.UUID) (ChatAutomation, error)
+	GetChatAutomationEventsByAutomationID(ctx context.Context, arg GetChatAutomationEventsByAutomationIDParams) ([]ChatAutomationEvent, error)
+	GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (ChatAutomationTrigger, error)
+	GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]ChatAutomationTrigger, error)
+	GetChatAutomations(ctx context.Context, arg GetChatAutomationsParams) ([]ChatAutomation, error)
 	GetChatByID(ctx context.Context, id uuid.UUID) (Chat, error)
 	GetChatByIDForUpdate(ctx context.Context, id uuid.UUID) (Chat, error)
 	// Per-root-chat cost breakdown for a single user within a date range.
@@ -696,6 +718,9 @@ type sqlcQuerier interface {
 	InsertAllUsersGroup(ctx context.Context, organizationID uuid.UUID) (Group, error)
 	InsertAuditLog(ctx context.Context, arg InsertAuditLogParams) (AuditLog, error)
 	InsertChat(ctx context.Context, arg InsertChatParams) (Chat, error)
+	InsertChatAutomation(ctx context.Context, arg InsertChatAutomationParams) (ChatAutomation, error)
+	InsertChatAutomationEvent(ctx context.Context, arg InsertChatAutomationEventParams) (ChatAutomationEvent, error)
+	InsertChatAutomationTrigger(ctx context.Context, arg InsertChatAutomationTriggerParams) (ChatAutomationTrigger, error)
 	InsertChatFile(ctx context.Context, arg InsertChatFileParams) (InsertChatFileRow, error)
 	InsertChatMessages(ctx context.Context, arg InsertChatMessagesParams) ([]ChatMessage, error)
 	InsertChatModelConfig(ctx context.Context, arg InsertChatModelConfigParams) (ChatModelConfig, error)
@@ -788,6 +813,10 @@ type sqlcQuerier interface {
 	// Returns paginated sessions with aggregated metadata, token counts, and
 	// the most recent user prompt. A "session" is a logical grouping of
 	// interceptions that share the same session_id (set by the client).
+	//
+	// Pagination-first strategy: identify the page of sessions cheaply via a
+	// single GROUP BY scan, then do expensive lateral joins (tokens, prompts,
+	// first-interception metadata) only for the ~page-size result set.
 	ListAIBridgeSessions(ctx context.Context, arg ListAIBridgeSessionsParams) ([]ListAIBridgeSessionsRow, error)
 	ListAIBridgeTokenUsagesByInterceptionIDs(ctx context.Context, interceptionIds []uuid.UUID) ([]AIBridgeTokenUsage, error)
 	ListAIBridgeToolUsagesByInterceptionIDs(ctx context.Context, interceptionIds []uuid.UUID) ([]AIBridgeToolUsage, error)
@@ -818,6 +847,10 @@ type sqlcQuerier interface {
 	// sequence, so this is acceptable.
 	PinChatByID(ctx context.Context, id uuid.UUID) error
 	PopNextQueuedMessage(ctx context.Context, chatID uuid.UUID) (ChatQueuedMessage, error)
+	// Deletes old chat automation events in bounded batches to avoid
+	// long-running locks on high-volume tables. Callers should loop
+	// until zero rows are returned.
+	PurgeOldChatAutomationEvents(ctx context.Context, arg PurgeOldChatAutomationEventsParams) (int64, error)
 	ReduceWorkspaceAgentShareLevelToAuthenticatedByTemplate(ctx context.Context, templateID uuid.UUID) error
 	RegisterWorkspaceProxy(ctx context.Context, arg RegisterWorkspaceProxyParams) (WorkspaceProxy, error)
 	RemoveUserFromGroups(ctx context.Context, arg RemoveUserFromGroupsParams) ([]uuid.UUID, error)
@@ -840,7 +873,7 @@ type sqlcQuerier interface {
 	// This must be called from within a transaction. The lock will be automatically
 	// released when the transaction ends.
 	TryAcquireLock(ctx context.Context, pgTryAdvisoryXactLock int64) (bool, error)
-	UnarchiveChatByID(ctx context.Context, id uuid.UUID) error
+	UnarchiveChatByID(ctx context.Context, id uuid.UUID) ([]Chat, error)
 	// This will always work regardless of the current state of the template version.
 	UnarchiveTemplateVersion(ctx context.Context, arg UnarchiveTemplateVersionParams) error
 	UnfavoriteWorkspace(ctx context.Context, id uuid.UUID) error
@@ -848,12 +881,21 @@ type sqlcQuerier interface {
 	UnsetDefaultChatModelConfigs(ctx context.Context) error
 	UpdateAIBridgeInterceptionEnded(ctx context.Context, arg UpdateAIBridgeInterceptionEndedParams) (AIBridgeInterception, error)
 	UpdateAPIKeyByID(ctx context.Context, arg UpdateAPIKeyByIDParams) error
+	UpdateChatAutomation(ctx context.Context, arg UpdateChatAutomationParams) (ChatAutomation, error)
+	UpdateChatAutomationTrigger(ctx context.Context, arg UpdateChatAutomationTriggerParams) (ChatAutomationTrigger, error)
+	UpdateChatAutomationTriggerLastTriggeredAt(ctx context.Context, arg UpdateChatAutomationTriggerLastTriggeredAtParams) error
+	UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, arg UpdateChatAutomationTriggerWebhookSecretParams) (ChatAutomationTrigger, error)
 	UpdateChatBuildAgentBinding(ctx context.Context, arg UpdateChatBuildAgentBindingParams) (Chat, error)
 	UpdateChatByID(ctx context.Context, arg UpdateChatByIDParams) (Chat, error)
 	// Bumps the heartbeat timestamp for a running chat so that other
 	// replicas know the worker is still alive.
 	UpdateChatHeartbeat(ctx context.Context, arg UpdateChatHeartbeatParams) (int64, error)
 	UpdateChatLabelsByID(ctx context.Context, arg UpdateChatLabelsByIDParams) (Chat, error)
+	// Updates the cached injected context parts (AGENTS.md +
+	// skills) on the chat row. Called only when context changes
+	// (first workspace attach or agent change). updated_at is
+	// intentionally not touched to avoid reordering the chat list.
+	UpdateChatLastInjectedContext(ctx context.Context, arg UpdateChatLastInjectedContextParams) (Chat, error)
 	UpdateChatLastModelConfigByID(ctx context.Context, arg UpdateChatLastModelConfigByIDParams) (Chat, error)
 	// Updates the last read message ID for a chat. This is used to track
 	// which messages the owner has seen, enabling unread indicators.

coderd/database/querier_test.go

@@ -1251,8 +1251,12 @@ func TestGetAuthorizedChats(t *testing.T) {
 	owner := dbgen.User(t, db, database.User{
 		RBACRoles: []string{rbac.RoleOwner().String()},
 	})
-	member := dbgen.User(t, db, database.User{})
-	secondMember := dbgen.User(t, db, database.User{})
+	member := dbgen.User(t, db, database.User{
+		RBACRoles: pq.StringArray{rbac.RoleAgentsAccess().String()},
+	})
+	secondMember := dbgen.User(t, db, database.User{
+		RBACRoles: pq.StringArray{rbac.RoleAgentsAccess().String()},
+	})
 
 	// Create FK dependencies: a chat provider and model config.
 	ctx := testutil.Context(t, testutil.WaitMedium)
@@ -1407,7 +1411,9 @@ func TestGetAuthorizedChats(t *testing.T) {
 
 		// Use a dedicated user for pagination to avoid interference
 		// with the other parallel subtests.
-		paginationUser := dbgen.User(t, db, database.User{})
+		paginationUser := dbgen.User(t, db, database.User{
+			RBACRoles: pq.StringArray{rbac.RoleAgentsAccess().String()},
+		})
 		for i := range 7 {
 			_, err := db.InsertChat(ctx, database.InsertChatParams{
 				OwnerID:           paginationUser.ID,
@@ -10640,7 +10646,8 @@ func TestChatPinOrderQueries(t *testing.T) {
 		}
 
 		// Archive the middle pin.
-		require.NoError(t, db.ArchiveChatByID(ctx, second.ID))
+		_, err := db.ArchiveChatByID(ctx, second.ID)
+		require.NoError(t, err)
 
 		// Archived chat should have pin_order cleared. Remaining
 		// pins keep their original positions; the next mutation

coderd/database/queries/aibridge.sql

@@ -454,95 +454,91 @@ WHERE
 -- Returns paginated sessions with aggregated metadata, token counts, and
 -- the most recent user prompt. A "session" is a logical grouping of
 -- interceptions that share the same session_id (set by the client).
-WITH filtered_interceptions AS (
+--
+-- Pagination-first strategy: identify the page of sessions cheaply via a
+-- single GROUP BY scan, then do expensive lateral joins (tokens, prompts,
+-- first-interception metadata) only for the ~page-size result set.
+WITH cursor_pos AS (
+	-- Resolve the cursor's started_at once, outside the HAVING clause,
+	-- so the planner cannot accidentally re-evaluate it per group.
+	SELECT MIN(aibridge_interceptions.started_at) AS started_at
+	FROM aibridge_interceptions
+	WHERE aibridge_interceptions.session_id = @after_session_id AND aibridge_interceptions.ended_at IS NOT NULL
+),
+session_page AS (
+	-- Paginate at the session level first; only cheap aggregates here.
 	SELECT
-		aibridge_interceptions.*
+		ai.session_id,
+		ai.initiator_id,
+		MIN(ai.started_at) AS started_at,
+		MAX(ai.ended_at) AS ended_at,
+		COUNT(*) FILTER (WHERE ai.thread_root_id IS NULL) AS threads
 	FROM
-		aibridge_interceptions
+		aibridge_interceptions ai
 	WHERE
 		-- Remove inflight interceptions (ones which lack an ended_at value).
-		aibridge_interceptions.ended_at IS NOT NULL
+		ai.ended_at IS NOT NULL
 		-- Filter by time frame
 		AND CASE
-			WHEN @started_after::timestamptz != '0001-01-01 00:00:00+00'::timestamptz THEN aibridge_interceptions.started_at >= @started_after::timestamptz
+			WHEN @started_after::timestamptz != '0001-01-01 00:00:00+00'::timestamptz THEN ai.started_at >= @started_after::timestamptz
 			ELSE true
 		END
 		AND CASE
-			WHEN @started_before::timestamptz != '0001-01-01 00:00:00+00'::timestamptz THEN aibridge_interceptions.started_at <= @started_before::timestamptz
+			WHEN @started_before::timestamptz != '0001-01-01 00:00:00+00'::timestamptz THEN ai.started_at <= @started_before::timestamptz
 			ELSE true
 		END
 		-- Filter initiator_id
 		AND CASE
-			WHEN @initiator_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN aibridge_interceptions.initiator_id = @initiator_id::uuid
+			WHEN @initiator_id::uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN ai.initiator_id = @initiator_id::uuid
 			ELSE true
 		END
 		-- Filter provider
 		AND CASE
-			WHEN @provider::text != '' THEN aibridge_interceptions.provider = @provider::text
+			WHEN @provider::text != '' THEN ai.provider = @provider::text
 			ELSE true
 		END
 		-- Filter model
 		AND CASE
-			WHEN @model::text != '' THEN aibridge_interceptions.model = @model::text
+			WHEN @model::text != '' THEN ai.model = @model::text
 			ELSE true
 		END
 		-- Filter client
 		AND CASE
-			WHEN @client::text != '' THEN COALESCE(aibridge_interceptions.client, 'Unknown') = @client::text
+			WHEN @client::text != '' THEN COALESCE(ai.client, 'Unknown') = @client::text
 			ELSE true
 		END
 		-- Filter session_id
 		AND CASE
-			WHEN @session_id::text != '' THEN aibridge_interceptions.session_id = @session_id::text
+			WHEN @session_id::text != '' THEN ai.session_id = @session_id::text
 			ELSE true
 		END
 		-- Authorize Filter clause will be injected below in ListAuthorizedAIBridgeSessions
 		-- @authorize_filter
-),
-session_tokens AS (
-	-- Aggregate token usage across all interceptions in each session.
-	-- Group by (session_id, initiator_id) to avoid merging sessions from
-	-- different users who happen to share the same client_session_id.
-	SELECT
-		fi.session_id,
-		fi.initiator_id,
-		COALESCE(SUM(tu.input_tokens), 0)::bigint AS input_tokens,
-		COALESCE(SUM(tu.output_tokens), 0)::bigint AS output_tokens
-		-- TODO: add extra token types once https://github.com/coder/aibridge/issues/150 lands.
-	FROM
-		filtered_interceptions fi
-	LEFT JOIN
-		aibridge_token_usages tu ON fi.id = tu.interception_id
 	GROUP BY
-		fi.session_id, fi.initiator_id
-),
-session_root AS (
-	-- Build one summary row per session. Group by (session_id, initiator_id)
-	-- to avoid merging sessions from different users who happen to share the
-	-- same client_session_id. The ARRAY_AGG with ORDER BY picks values from
-	-- the chronologically first interception for fields that should represent
-	-- the session as a whole (client, metadata). Threads are counted as
-	-- distinct root interception IDs: an interception with a NULL
-	-- thread_root_id is itself a thread root.
-	SELECT
-		fi.session_id,
-		fi.initiator_id,
-		(ARRAY_AGG(fi.client ORDER BY fi.started_at, fi.id))[1] AS client,
-		(ARRAY_AGG(fi.metadata ORDER BY fi.started_at, fi.id))[1] AS metadata,
-		ARRAY_AGG(DISTINCT fi.provider ORDER BY fi.provider) AS providers,
-		ARRAY_AGG(DISTINCT fi.model ORDER BY fi.model) AS models,
-		MIN(fi.started_at) AS started_at,
-		MAX(fi.ended_at) AS ended_at,
-		COUNT(DISTINCT COALESCE(fi.thread_root_id, fi.id)) AS threads,
-		-- Collect IDs for lateral prompt lookup.
-		ARRAY_AGG(fi.id) AS interception_ids
-	FROM
-		filtered_interceptions fi
-	GROUP BY
-		fi.session_id, fi.initiator_id
+		ai.session_id, ai.initiator_id
+	HAVING
+		-- Cursor pagination: uses a composite (started_at, session_id)
+		-- cursor to support keyset pagination. The less-than comparison
+		-- matches the DESC sort order so rows after the cursor come
+		-- later in results. The cursor value comes from cursor_pos to
+		-- guarantee single evaluation.
+		CASE
+			WHEN @after_session_id::text != '' THEN (
+				(MIN(ai.started_at), ai.session_id) < (
+					(SELECT started_at FROM cursor_pos),
+					@after_session_id::text
+				)
+			)
+			ELSE true
+		END
+	ORDER BY
+		MIN(ai.started_at) DESC,
+		ai.session_id DESC
+	LIMIT COALESCE(NULLIF(@limit_::integer, 0), 100)
+	OFFSET @offset_
 )
 SELECT
-	sr.session_id,
+	sp.session_id,
 	visible_users.id AS user_id,
 	visible_users.username AS user_username,
 	visible_users.name AS user_name,
@@ -551,45 +547,48 @@ SELECT
 	sr.models::text[] AS models,
 	COALESCE(sr.client, '')::varchar(64) AS client,
 	sr.metadata::jsonb AS metadata,
-	sr.started_at::timestamptz AS started_at,
-	sr.ended_at::timestamptz AS ended_at,
-	sr.threads,
+	sp.started_at::timestamptz AS started_at,
+	sp.ended_at::timestamptz AS ended_at,
+	sp.threads,
 	COALESCE(st.input_tokens, 0)::bigint AS input_tokens,
 	COALESCE(st.output_tokens, 0)::bigint AS output_tokens,
 	COALESCE(slp.prompt, '') AS last_prompt
 FROM
-	session_root sr
+	session_page sp
 JOIN
-	visible_users ON visible_users.id = sr.initiator_id
-LEFT JOIN
-	session_tokens st ON st.session_id = sr.session_id AND st.initiator_id = sr.initiator_id
+	visible_users ON visible_users.id = sp.initiator_id
 LEFT JOIN LATERAL (
-	-- Lateral join to efficiently fetch only the most recent user prompt
-	-- across all interceptions in the session, avoiding a full aggregation.
+	SELECT
+		(ARRAY_AGG(ai.client ORDER BY ai.started_at, ai.id))[1] AS client,
+		(ARRAY_AGG(ai.metadata ORDER BY ai.started_at, ai.id))[1] AS metadata,
+		ARRAY_AGG(DISTINCT ai.provider ORDER BY ai.provider) AS providers,
+		ARRAY_AGG(DISTINCT ai.model ORDER BY ai.model) AS models,
+		ARRAY_AGG(ai.id) AS interception_ids
+	FROM aibridge_interceptions ai
+	WHERE ai.session_id = sp.session_id
+		AND ai.initiator_id = sp.initiator_id
+		AND ai.ended_at IS NOT NULL
+) sr ON true
+LEFT JOIN LATERAL (
+	-- Aggregate tokens only for this session's interceptions.
+	SELECT
+		COALESCE(SUM(tu.input_tokens), 0)::bigint AS input_tokens,
+		COALESCE(SUM(tu.output_tokens), 0)::bigint AS output_tokens
+	FROM aibridge_token_usages tu
+	WHERE tu.interception_id = ANY(sr.interception_ids)
+) st ON true
+LEFT JOIN LATERAL (
+	-- Fetch only the most recent user prompt across all interceptions
+	-- in the session.
 	SELECT up.prompt
 	FROM aibridge_user_prompts up
 	WHERE up.interception_id = ANY(sr.interception_ids)
 	ORDER BY up.created_at DESC, up.id DESC
 	LIMIT 1
 ) slp ON true
-WHERE
-	-- Cursor pagination: uses a composite (started_at, session_id) cursor
-	-- to support keyset pagination. The less-than comparison matches the
-	-- DESC sort order so that rows after the cursor come later in results.
-	CASE
-		WHEN @after_session_id::text != '' THEN (
-			(sr.started_at, sr.session_id) < (
-				(SELECT started_at FROM session_root WHERE session_id = @after_session_id),
-				@after_session_id::text
-			)
-		)
-		ELSE true
-	END
 ORDER BY
-	sr.started_at DESC,
-	sr.session_id DESC
-LIMIT COALESCE(NULLIF(@limit_::integer, 0), 100)
-OFFSET @offset_
+	sp.started_at DESC,
+	sp.session_id DESC
 ;
 
 -- name: ListAIBridgeSessionThreads :many

coderd/database/queries/chatautomationevents.sql

@@ -0,0 +1,80 @@
+-- name: InsertChatAutomationEvent :one
+INSERT INTO chat_automation_events (
+    id,
+    automation_id,
+    trigger_id,
+    received_at,
+    payload,
+    filter_matched,
+    resolved_labels,
+    matched_chat_id,
+    created_chat_id,
+    status,
+    error
+) VALUES (
+    @id::uuid,
+    @automation_id::uuid,
+    sqlc.narg('trigger_id')::uuid,
+    @received_at::timestamptz,
+    @payload::jsonb,
+    @filter_matched::boolean,
+    sqlc.narg('resolved_labels')::jsonb,
+    sqlc.narg('matched_chat_id')::uuid,
+    sqlc.narg('created_chat_id')::uuid,
+    @status::chat_automation_event_status,
+    sqlc.narg('error')::text
+) RETURNING *;
+
+-- name: GetChatAutomationEventsByAutomationID :many
+SELECT
+    *
+FROM
+    chat_automation_events
+WHERE
+    automation_id = @automation_id::uuid
+    AND CASE
+        WHEN sqlc.narg('status_filter')::chat_automation_event_status IS NOT NULL THEN status = sqlc.narg('status_filter')::chat_automation_event_status
+        ELSE true
+    END
+ORDER BY
+    received_at DESC
+OFFSET @offset_opt
+LIMIT
+    COALESCE(NULLIF(@limit_opt :: int, 0), 50);
+
+-- name: CountChatAutomationChatCreatesInWindow :one
+-- Counts new-chat events in the rate-limit window. This count is
+-- approximate under concurrency: concurrent webhook handlers may
+-- each read the same count before any of them insert, so brief
+-- bursts can slightly exceed the configured cap.
+SELECT COUNT(*)
+FROM chat_automation_events
+WHERE automation_id = @automation_id::uuid
+    AND status = 'created'
+    AND received_at > @window_start::timestamptz;
+
+-- name: CountChatAutomationMessagesInWindow :one
+-- Counts total message events (creates + continues) in the rate-limit
+-- window. This count is approximate under concurrency: concurrent
+-- webhook handlers may each read the same count before any of them
+-- insert, so brief bursts can slightly exceed the configured cap.
+SELECT COUNT(*)
+FROM chat_automation_events
+WHERE automation_id = @automation_id::uuid
+    AND status IN ('created', 'continued')
+    AND received_at > @window_start::timestamptz;
+
+-- name: PurgeOldChatAutomationEvents :execrows
+-- Deletes old chat automation events in bounded batches to avoid
+-- long-running locks on high-volume tables. Callers should loop
+-- until zero rows are returned.
+WITH old_events AS (
+    SELECT id
+    FROM chat_automation_events
+    WHERE received_at < @before::timestamptz
+    ORDER BY received_at ASC
+    LIMIT @limit_count
+)
+DELETE FROM chat_automation_events
+USING old_events
+WHERE chat_automation_events.id = old_events.id;

coderd/database/queries/chatautomations.sql

@@ -0,0 +1,85 @@
+-- name: InsertChatAutomation :one
+INSERT INTO chat_automations (
+    id,
+    owner_id,
+    organization_id,
+    name,
+    description,
+    instructions,
+    model_config_id,
+    mcp_server_ids,
+    allowed_tools,
+    status,
+    max_chat_creates_per_hour,
+    max_messages_per_hour,
+    created_at,
+    updated_at
+) VALUES (
+    @id::uuid,
+    @owner_id::uuid,
+    @organization_id::uuid,
+    @name::text,
+    @description::text,
+    @instructions::text,
+    sqlc.narg('model_config_id')::uuid,
+    COALESCE(@mcp_server_ids::uuid[], '{}'::uuid[]),
+    COALESCE(@allowed_tools::text[], '{}'::text[]),
+    @status::chat_automation_status,
+    @max_chat_creates_per_hour::integer,
+    @max_messages_per_hour::integer,
+    @created_at::timestamptz,
+    @updated_at::timestamptz
+) RETURNING *;
+
+-- name: GetChatAutomationByID :one
+SELECT * FROM chat_automations WHERE id = @id::uuid;
+
+-- name: GetChatAutomations :many
+SELECT
+    *
+FROM
+    chat_automations
+WHERE
+    CASE
+        WHEN @owner_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN chat_automations.owner_id = @owner_id
+        ELSE true
+    END
+    AND CASE
+        WHEN @organization_id :: uuid != '00000000-0000-0000-0000-000000000000'::uuid THEN chat_automations.organization_id = @organization_id
+        ELSE true
+    END
+    -- Authorize Filter clause will be injected below in GetAuthorizedChatAutomations
+    -- @authorize_filter
+ORDER BY
+    created_at DESC, id DESC
+OFFSET @offset_opt
+LIMIT
+    COALESCE(NULLIF(@limit_opt :: int, 0), 50);
+
+-- name: UpdateChatAutomation :one
+UPDATE chat_automations SET
+    name = @name::text,
+    description = @description::text,
+    instructions = @instructions::text,
+    model_config_id = sqlc.narg('model_config_id')::uuid,
+    mcp_server_ids = COALESCE(@mcp_server_ids::uuid[], '{}'::uuid[]),
+    allowed_tools = COALESCE(@allowed_tools::text[], '{}'::text[]),
+    status = @status::chat_automation_status,
+    max_chat_creates_per_hour = @max_chat_creates_per_hour::integer,
+    max_messages_per_hour = @max_messages_per_hour::integer,
+    updated_at = @updated_at::timestamptz
+WHERE id = @id::uuid
+RETURNING *;
+
+-- name: DeleteChatAutomationByID :exec
+DELETE FROM chat_automations WHERE id = @id::uuid;
+
+-- name: CleanupDeletedMCPServerIDsFromChatAutomations :exec
+UPDATE chat_automations
+SET mcp_server_ids = (
+    SELECT COALESCE(array_agg(sid), '{}')
+    FROM unnest(chat_automations.mcp_server_ids) AS sid
+    WHERE sid IN (SELECT id FROM mcp_server_configs)
+)
+WHERE mcp_server_ids != '{}'
+  AND NOT (mcp_server_ids <@ COALESCE((SELECT array_agg(id) FROM mcp_server_configs), '{}'));

coderd/database/queries/chatautomationtriggers.sql

@@ -0,0 +1,87 @@
+-- name: InsertChatAutomationTrigger :one
+INSERT INTO chat_automation_triggers (
+    id,
+    automation_id,
+    type,
+    webhook_secret,
+    webhook_secret_key_id,
+    cron_schedule,
+    filter,
+    label_paths,
+    created_at,
+    updated_at
+) VALUES (
+    @id::uuid,
+    @automation_id::uuid,
+    @type::chat_automation_trigger_type,
+    sqlc.narg('webhook_secret')::text,
+    sqlc.narg('webhook_secret_key_id')::text,
+    sqlc.narg('cron_schedule')::text,
+    sqlc.narg('filter')::jsonb,
+    sqlc.narg('label_paths')::jsonb,
+    @created_at::timestamptz,
+    @updated_at::timestamptz
+) RETURNING *;
+
+-- name: GetChatAutomationTriggerByID :one
+SELECT * FROM chat_automation_triggers WHERE id = @id::uuid;
+
+-- name: GetChatAutomationTriggersByAutomationID :many
+SELECT * FROM chat_automation_triggers
+WHERE automation_id = @automation_id::uuid
+ORDER BY created_at ASC;
+
+-- name: UpdateChatAutomationTrigger :one
+UPDATE chat_automation_triggers SET
+    cron_schedule = COALESCE(sqlc.narg('cron_schedule'), cron_schedule),
+    filter = COALESCE(sqlc.narg('filter'), filter),
+    label_paths = COALESCE(sqlc.narg('label_paths'), label_paths),
+    updated_at = @updated_at::timestamptz
+WHERE id = @id::uuid
+RETURNING *;
+
+-- name: UpdateChatAutomationTriggerWebhookSecret :one
+UPDATE chat_automation_triggers SET
+    webhook_secret = sqlc.narg('webhook_secret')::text,
+    webhook_secret_key_id = sqlc.narg('webhook_secret_key_id')::text,
+    updated_at = @updated_at::timestamptz
+WHERE id = @id::uuid
+RETURNING *;
+
+-- name: DeleteChatAutomationTriggerByID :exec
+DELETE FROM chat_automation_triggers WHERE id = @id::uuid;
+
+-- name: GetActiveChatAutomationCronTriggers :many
+-- Returns all cron triggers whose parent automation is active or in
+-- preview mode. The scheduler uses this to evaluate which triggers
+-- are due.
+SELECT
+    t.id,
+    t.automation_id,
+    t.type,
+    t.cron_schedule,
+    t.filter,
+    t.label_paths,
+    t.last_triggered_at,
+    t.created_at,
+    t.updated_at,
+    a.status AS automation_status,
+    a.owner_id AS automation_owner_id,
+    a.instructions AS automation_instructions,
+    a.name AS automation_name,
+    a.organization_id AS automation_organization_id,
+    a.model_config_id AS automation_model_config_id,
+    a.mcp_server_ids AS automation_mcp_server_ids,
+    a.allowed_tools AS automation_allowed_tools,
+    a.max_chat_creates_per_hour AS automation_max_chat_creates_per_hour,
+    a.max_messages_per_hour AS automation_max_messages_per_hour
+FROM chat_automation_triggers t
+JOIN chat_automations a ON a.id = t.automation_id
+WHERE t.type = 'cron'
+  AND t.cron_schedule IS NOT NULL
+  AND a.status IN ('active', 'preview');
+
+-- name: UpdateChatAutomationTriggerLastTriggeredAt :exec
+UPDATE chat_automation_triggers
+SET last_triggered_at = @last_triggered_at::timestamptz
+WHERE id = @id::uuid;

coderd/database/queries/chats.sql

@@ -1,9 +1,24 @@
--- name: ArchiveChatByID :exec
-UPDATE chats SET archived = true, pin_order = 0, updated_at = NOW()
-WHERE id = @id OR root_chat_id = @id;
+-- name: ArchiveChatByID :many
+WITH chats AS (
+    UPDATE chats
+    SET archived = true, pin_order = 0, updated_at = NOW()
+    WHERE id = @id::uuid OR root_chat_id = @id::uuid
+    RETURNING *
+)
+SELECT *
+FROM chats
+ORDER BY (id = @id::uuid) DESC, created_at ASC, id ASC;
 
--- name: UnarchiveChatByID :exec
-UPDATE chats SET archived = false, updated_at = NOW() WHERE id = @id::uuid;
+-- name: UnarchiveChatByID :many
+WITH chats AS (
+    UPDATE chats
+    SET archived = false, updated_at = NOW()
+    WHERE id = @id::uuid OR root_chat_id = @id::uuid
+    RETURNING *
+)
+SELECT *
+FROM chats
+ORDER BY (id = @id::uuid) DESC, created_at ASC, id ASC;
 
 -- name: PinChatByID :exec
 WITH target_chat AS (
@@ -528,6 +543,17 @@ WHERE
     id = @id::uuid
 RETURNING *;
 
+-- name: UpdateChatLastInjectedContext :one
+-- Updates the cached injected context parts (AGENTS.md +
+-- skills) on the chat row. Called only when context changes
+-- (first workspace attach or agent change). updated_at is
+-- intentionally not touched to avoid reordering the chat list.
+UPDATE chats SET
+    last_injected_context = sqlc.narg('last_injected_context')::jsonb
+WHERE
+    id = @id::uuid
+RETURNING *;
+
 -- name: UpdateChatMCPServerIDs :one
 UPDATE
     chats

coderd/database/sqlc.yaml

@@ -247,6 +247,8 @@ sql:
           mcp_server_tool_snapshots: MCPServerToolSnapshots
           mcp_server_config_id: MCPServerConfigID
           mcp_server_ids: MCPServerIDs
+          automation_mcp_server_ids: AutomationMCPServerIDs
+          webhook_secret_key_id: WebhookSecretKeyID
           icon_url: IconURL
           oauth2_client_id: OAuth2ClientID
           oauth2_client_secret: OAuth2ClientSecret

coderd/database/unique_constraint.go

@@ -15,6 +15,9 @@ const (
 	UniqueAPIKeysPkey                                         UniqueConstraint = "api_keys_pkey"                                                   // ALTER TABLE ONLY api_keys ADD CONSTRAINT api_keys_pkey PRIMARY KEY (id);
 	UniqueAuditLogsPkey                                       UniqueConstraint = "audit_logs_pkey"                                                 // ALTER TABLE ONLY audit_logs ADD CONSTRAINT audit_logs_pkey PRIMARY KEY (id);
 	UniqueBoundaryUsageStatsPkey                              UniqueConstraint = "boundary_usage_stats_pkey"                                       // ALTER TABLE ONLY boundary_usage_stats ADD CONSTRAINT boundary_usage_stats_pkey PRIMARY KEY (replica_id);
+	UniqueChatAutomationEventsPkey                            UniqueConstraint = "chat_automation_events_pkey"                                     // ALTER TABLE ONLY chat_automation_events ADD CONSTRAINT chat_automation_events_pkey PRIMARY KEY (id);
+	UniqueChatAutomationTriggersPkey                          UniqueConstraint = "chat_automation_triggers_pkey"                                   // ALTER TABLE ONLY chat_automation_triggers ADD CONSTRAINT chat_automation_triggers_pkey PRIMARY KEY (id);
+	UniqueChatAutomationsPkey                                 UniqueConstraint = "chat_automations_pkey"                                           // ALTER TABLE ONLY chat_automations ADD CONSTRAINT chat_automations_pkey PRIMARY KEY (id);
 	UniqueChatDiffStatusesPkey                                UniqueConstraint = "chat_diff_statuses_pkey"                                         // ALTER TABLE ONLY chat_diff_statuses ADD CONSTRAINT chat_diff_statuses_pkey PRIMARY KEY (chat_id);
 	UniqueChatFilesPkey                                       UniqueConstraint = "chat_files_pkey"                                                 // ALTER TABLE ONLY chat_files ADD CONSTRAINT chat_files_pkey PRIMARY KEY (id);
 	UniqueChatMessagesPkey                                    UniqueConstraint = "chat_messages_pkey"                                              // ALTER TABLE ONLY chat_messages ADD CONSTRAINT chat_messages_pkey PRIMARY KEY (id);
@@ -125,6 +128,7 @@ const (
 	UniqueWorkspaceResourcesPkey                              UniqueConstraint = "workspace_resources_pkey"                                        // ALTER TABLE ONLY workspace_resources ADD CONSTRAINT workspace_resources_pkey PRIMARY KEY (id);
 	UniqueWorkspacesPkey                                      UniqueConstraint = "workspaces_pkey"                                                 // ALTER TABLE ONLY workspaces ADD CONSTRAINT workspaces_pkey PRIMARY KEY (id);
 	UniqueIndexAPIKeyName                                     UniqueConstraint = "idx_api_key_name"                                                // CREATE UNIQUE INDEX idx_api_key_name ON api_keys USING btree (user_id, token_name) WHERE (login_type = 'token'::login_type);
+	UniqueIndexChatAutomationsOwnerOrgName                    UniqueConstraint = "idx_chat_automations_owner_org_name"                             // CREATE UNIQUE INDEX idx_chat_automations_owner_org_name ON chat_automations USING btree (owner_id, organization_id, name);
 	UniqueIndexChatModelConfigsSingleDefault                  UniqueConstraint = "idx_chat_model_configs_single_default"                           // CREATE UNIQUE INDEX idx_chat_model_configs_single_default ON chat_model_configs USING btree ((1)) WHERE ((is_default = true) AND (deleted = false));
 	UniqueIndexConnectionLogsConnectionIDWorkspaceIDAgentName UniqueConstraint = "idx_connection_logs_connection_id_workspace_id_agent_name"       // CREATE UNIQUE INDEX idx_connection_logs_connection_id_workspace_id_agent_name ON connection_logs USING btree (connection_id, workspace_id, agent_name);
 	UniqueIndexCustomRolesNameLowerOrganizationID             UniqueConstraint = "idx_custom_roles_name_lower_organization_id"                     // CREATE UNIQUE INDEX idx_custom_roles_name_lower_organization_id ON custom_roles USING btree (lower(name), COALESCE(organization_id, '00000000-0000-0000-0000-000000000000'::uuid));

coderd/exp_chats.go

@@ -393,6 +393,11 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 	apiKey := httpmw.APIKey(r)
 
+	if !api.Authorize(r, policy.ActionCreate, rbac.ResourceChat.WithOwner(apiKey.UserID.String())) {
+		httpapi.Forbidden(rw)
+		return
+	}
+
 	var req codersdk.CreateChatRequest
 	if !httpapi.Read(ctx, rw, r, &req) {
 		return
@@ -498,6 +503,10 @@ func (api *API) postChats(rw http.ResponseWriter, r *http.Request) {
 			})
 			return
 		}
+		if dbauthz.IsNotAuthorizedError(err) {
+			httpapi.Forbidden(rw)
+			return
+		}
 		httpapi.Write(ctx, rw, http.StatusInternalServerError, codersdk.Response{
 			Message: "Failed to create chat.",
 			Detail:  err.Error(),
@@ -616,6 +625,10 @@ func (api *API) chatCostSummary(rw http.ResponseWriter, r *http.Request) {
 		EndDate:   endDate,
 	})
 	if err != nil {
+		if dbauthz.IsNotAuthorizedError(err) {
+			httpapi.Forbidden(rw)
+			return
+		}
 		httpapi.InternalServerError(rw, err)
 		return
 	}
@@ -626,6 +639,10 @@ func (api *API) chatCostSummary(rw http.ResponseWriter, r *http.Request) {
 		EndDate:   endDate,
 	})
 	if err != nil {
+		if dbauthz.IsNotAuthorizedError(err) {
+			httpapi.Forbidden(rw)
+			return
+		}
 		httpapi.InternalServerError(rw, err)
 		return
 	}
@@ -636,6 +653,10 @@ func (api *API) chatCostSummary(rw http.ResponseWriter, r *http.Request) {
 		EndDate:   endDate,
 	})
 	if err != nil {
+		if dbauthz.IsNotAuthorizedError(err) {
+			httpapi.Forbidden(rw)
+			return
+		}
 		httpapi.InternalServerError(rw, err)
 		return
 	}
@@ -1620,20 +1641,20 @@ func (api *API) patchChat(rw http.ResponseWriter, r *http.Request) {
 		}
 
 		var err error
-		// Use chatDaemon when available so it can notify active
-		// subscribers. Fall back to direct DB for the simple
-		// archive flag — no streaming state is involved.
+		// Use chatDaemon when available so it can interrupt active
+		// processing before broadcasting archive state. Fall back to
+		// direct DB when no daemon is running.
 		if archived {
 			if api.chatDaemon != nil {
 				err = api.chatDaemon.ArchiveChat(ctx, chat)
 			} else {
-				err = api.Database.ArchiveChatByID(ctx, chat.ID)
+				_, err = api.Database.ArchiveChatByID(ctx, chat.ID)
 			}
 		} else {
 			if api.chatDaemon != nil {
 				err = api.chatDaemon.UnarchiveChat(ctx, chat)
 			} else {
-				err = api.Database.UnarchiveChatByID(ctx, chat.ID)
+				_, err = api.Database.UnarchiveChatByID(ctx, chat.ID)
 			}
 		}
 		if err != nil {

coderd/exp_chats_test.go

@@ -194,10 +194,15 @@ func TestPostChats(t *testing.T) {
 
 		ctx := testutil.Context(t, testutil.WaitLong)
 		client := newChatClient(t)
-		user := coderdtest.CreateFirstUser(t, client.Client)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
 		modelConfig := createChatModelConfig(t, client)
 
-		chat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+		// Use a member with agents-access instead of the owner to
+		// verify least-privilege access.
+		memberClientRaw, member := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
+		memberClient := codersdk.NewExperimentalClient(memberClientRaw)
+
+		chat, err := memberClient.CreateChat(ctx, codersdk.CreateChatRequest{
 			Content: []codersdk.ChatInputPart{
 				{
 					Type: codersdk.ChatInputPartTypeText,
@@ -208,19 +213,18 @@ func TestPostChats(t *testing.T) {
 		require.NoError(t, err)
 
 		require.NotEqual(t, uuid.Nil, chat.ID)
-		require.Equal(t, user.UserID, chat.OwnerID)
+		require.Equal(t, member.ID, chat.OwnerID)
 		require.Equal(t, modelConfig.ID, chat.LastModelConfigID)
 		require.Equal(t, "hello from chats route tests", chat.Title)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 		require.NotZero(t, chat.CreatedAt)
 		require.NotZero(t, chat.UpdatedAt)
 		require.Nil(t, chat.WorkspaceID)
 		require.NotNil(t, chat.RootChatID)
 		require.Equal(t, chat.ID, *chat.RootChatID)
 
-		chatResult, err := client.GetChat(ctx, chat.ID)
+		chatResult, err := memberClient.GetChat(ctx, chat.ID)
 		require.NoError(t, err)
-		messagesResult, err := client.GetChatMessages(ctx, chat.ID, nil)
+		messagesResult, err := memberClient.GetChatMessages(ctx, chat.ID, nil)
 		require.NoError(t, err)
 		require.Equal(t, chat.ID, chatResult.ID)
 
@@ -240,6 +244,29 @@ func TestPostChats(t *testing.T) {
 		require.True(t, foundUserMessage)
 	})
 
+	t.Run("MemberWithoutAgentsAccess", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client := newChatClient(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		_ = createChatModelConfig(t, client)
+
+		// Member without agents-access should be denied.
+		memberClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		memberClient := codersdk.NewExperimentalClient(memberClientRaw)
+
+		_, err := memberClient.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "this should fail",
+				},
+			},
+		})
+		requireSDKError(t, err, http.StatusForbidden)
+	})
+
 	t.Run("HidesSystemPromptMessages", func(t *testing.T) {
 		t.Parallel()
 
@@ -271,7 +298,7 @@ func TestPostChats(t *testing.T) {
 		ctx := testutil.Context(t, testutil.WaitLong)
 		adminClient, db := newChatClientWithDatabase(t)
 		firstUser := coderdtest.CreateFirstUser(t, adminClient.Client)
-		memberClientRaw, _ := coderdtest.CreateAnotherUser(t, adminClient.Client, firstUser.OrganizationID)
+		memberClientRaw, _ := coderdtest.CreateAnotherUser(t, adminClient.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		memberClient := codersdk.NewExperimentalClient(memberClientRaw)
 
 		workspaceBuild := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
@@ -307,6 +334,7 @@ func TestPostChats(t *testing.T) {
 			adminClient.Client,
 			firstUser.OrganizationID,
 			rbac.ScopedRoleOrgAdmin(firstUser.OrganizationID),
+			rbac.RoleAgentsAccess(),
 		)
 		orgAdminClient := codersdk.NewExperimentalClient(orgAdminClientRaw)
 
@@ -518,7 +546,7 @@ func TestListChats(t *testing.T) {
 		})
 		require.NoError(t, err)
 
-		memberClientRaw, member := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		memberClientRaw, member := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		memberClient := codersdk.NewExperimentalClient(memberClientRaw)
 		memberDBChat, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
 			OwnerID:           member.ID,
@@ -586,6 +614,32 @@ func TestListChats(t *testing.T) {
 		require.Equal(t, memberChats[0].ID, memberChats[0].DiffStatus.ChatID)
 	})
 
+	t.Run("MemberWithoutAgentsAccess", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, db := newChatClientWithDatabase(t)
+		firstUser := coderdtest.CreateFirstUser(t, client.Client)
+		modelConfig := createChatModelConfig(t, client)
+
+		// Create a member without agents-access and insert a chat
+		// owned by them via system context. This verifies the
+		// RBAC filter actually excludes results rather than
+		// returning empty because no chats exist.
+		memberClientRaw, member := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		memberClient := codersdk.NewExperimentalClient(memberClientRaw)
+		_, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
+			OwnerID:           member.ID,
+			LastModelConfigID: modelConfig.ID,
+			Title:             "member chat",
+		})
+		require.NoError(t, err)
+
+		chats, err := memberClient.ListChats(ctx, nil)
+		require.NoError(t, err)
+		require.Empty(t, chats)
+	})
+
 	t.Run("Unauthenticated", func(t *testing.T) {
 		t.Parallel()
 
@@ -997,6 +1051,102 @@ func TestWatchChats(t *testing.T) {
 		}
 	})
 
+	t.Run("ArchiveAndUnarchiveEmitEventsForDescendants", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, db := newChatClientWithDatabase(t)
+		user := coderdtest.CreateFirstUser(t, client.Client)
+		modelConfig := createChatModelConfig(t, client)
+
+		parentChat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "watch root chat",
+				},
+			},
+		})
+		require.NoError(t, err)
+
+		childOne, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
+			OwnerID:           user.UserID,
+			LastModelConfigID: modelConfig.ID,
+			Title:             "watch child 1",
+			ParentChatID:      uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+			RootChatID:        uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+		})
+		require.NoError(t, err)
+
+		childTwo, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
+			OwnerID:           user.UserID,
+			LastModelConfigID: modelConfig.ID,
+			Title:             "watch child 2",
+			ParentChatID:      uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+			RootChatID:        uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+		})
+		require.NoError(t, err)
+
+		conn, err := client.Dial(ctx, "/api/experimental/chats/watch", nil)
+		require.NoError(t, err)
+		defer conn.Close(websocket.StatusNormalClosure, "done")
+
+		type watchEvent struct {
+			Type codersdk.ServerSentEventType `json:"type"`
+			Data json.RawMessage              `json:"data,omitempty"`
+		}
+
+		var ping watchEvent
+		err = wsjson.Read(ctx, conn, &ping)
+		require.NoError(t, err)
+		require.Equal(t, codersdk.ServerSentEventTypePing, ping.Type)
+
+		collectLifecycleEvents := func(expectedKind coderdpubsub.ChatEventKind) map[uuid.UUID]coderdpubsub.ChatEvent {
+			t.Helper()
+
+			events := make(map[uuid.UUID]coderdpubsub.ChatEvent, 3)
+			for len(events) < 3 {
+				var update watchEvent
+				err = wsjson.Read(ctx, conn, &update)
+				require.NoError(t, err)
+				if update.Type == codersdk.ServerSentEventTypePing {
+					continue
+				}
+				require.Equal(t, codersdk.ServerSentEventTypeData, update.Type)
+
+				var payload coderdpubsub.ChatEvent
+				err = json.Unmarshal(update.Data, &payload)
+				require.NoError(t, err)
+				if payload.Kind != expectedKind {
+					continue
+				}
+				events[payload.Chat.ID] = payload
+			}
+			return events
+		}
+
+		assertLifecycleEvents := func(events map[uuid.UUID]coderdpubsub.ChatEvent, archived bool) {
+			t.Helper()
+
+			require.Len(t, events, 3)
+			for _, chatID := range []uuid.UUID{parentChat.ID, childOne.ID, childTwo.ID} {
+				payload, ok := events[chatID]
+				require.True(t, ok, "missing event for chat %s", chatID)
+				require.Equal(t, archived, payload.Chat.Archived)
+			}
+		}
+
+		err = client.UpdateChat(ctx, parentChat.ID, codersdk.UpdateChatRequest{Archived: ptr.Ref(true)})
+		require.NoError(t, err)
+		deletedEvents := collectLifecycleEvents(coderdpubsub.ChatEventKindDeleted)
+		assertLifecycleEvents(deletedEvents, true)
+
+		err = client.UpdateChat(ctx, parentChat.ID, codersdk.UpdateChatRequest{Archived: ptr.Ref(false)})
+		require.NoError(t, err)
+		createdEvents := collectLifecycleEvents(coderdpubsub.ChatEventKindCreated)
+		assertLifecycleEvents(createdEvents, false)
+	})
+
 	t.Run("Unauthenticated", func(t *testing.T) {
 		t.Parallel()
 
@@ -1958,7 +2108,7 @@ func TestGetChat(t *testing.T) {
 		})
 		require.NoError(t, err)
 
-		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		otherClient := codersdk.NewExperimentalClient(otherClientRaw)
 		_, err = otherClient.GetChat(ctx, createdChat.ID)
 		requireSDKError(t, err, http.StatusNotFound)
@@ -2155,6 +2305,96 @@ func TestUnarchiveChat(t *testing.T) {
 		require.Empty(t, archivedChats)
 	})
 
+	t.Run("UnarchivesChildren", func(t *testing.T) {
+		t.Parallel()
+
+		ctx := testutil.Context(t, testutil.WaitLong)
+		client, db := newChatClientWithDatabase(t)
+		user := coderdtest.CreateFirstUser(t, client.Client)
+		modelConfig := createChatModelConfig(t, client)
+
+		parentChat, err := client.CreateChat(ctx, codersdk.CreateChatRequest{
+			Content: []codersdk.ChatInputPart{
+				{
+					Type: codersdk.ChatInputPartTypeText,
+					Text: "parent chat",
+				},
+			},
+		})
+		require.NoError(t, err)
+
+		child1, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
+			OwnerID:           user.UserID,
+			LastModelConfigID: modelConfig.ID,
+			Title:             "child 1",
+			ParentChatID:      uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+			RootChatID:        uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+		})
+		require.NoError(t, err)
+
+		child2, err := db.InsertChat(dbauthz.AsSystemRestricted(ctx), database.InsertChatParams{
+			OwnerID:           user.UserID,
+			LastModelConfigID: modelConfig.ID,
+			Title:             "child 2",
+			ParentChatID:      uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+			RootChatID:        uuid.NullUUID{UUID: parentChat.ID, Valid: true},
+		})
+		require.NoError(t, err)
+
+		err = client.UpdateChat(ctx, parentChat.ID, codersdk.UpdateChatRequest{Archived: ptr.Ref(true)})
+		require.NoError(t, err)
+
+		err = client.UpdateChat(ctx, parentChat.ID, codersdk.UpdateChatRequest{Archived: ptr.Ref(false)})
+		require.NoError(t, err)
+
+		activeChats, err := client.ListChats(ctx, &codersdk.ListChatsOptions{
+			Query: "archived:false",
+		})
+		require.NoError(t, err)
+
+		var foundParent bool
+		var foundChild1 bool
+		var foundChild2 bool
+		for _, chat := range activeChats {
+			switch chat.ID {
+			case parentChat.ID:
+				foundParent = true
+				require.False(t, chat.Archived)
+			case child1.ID:
+				foundChild1 = true
+				require.False(t, chat.Archived)
+			case child2.ID:
+				foundChild2 = true
+				require.False(t, chat.Archived)
+			}
+		}
+		require.True(t, foundParent, "parent should be listed as active")
+		require.True(t, foundChild1, "child1 should be listed as active")
+		require.True(t, foundChild2, "child2 should be listed as active")
+
+		archivedChats, err := client.ListChats(ctx, &codersdk.ListChatsOptions{
+			Query: "archived:true",
+		})
+		require.NoError(t, err)
+		for _, chat := range archivedChats {
+			require.NotEqual(t, parentChat.ID, chat.ID, "parent should not remain archived")
+			require.NotEqual(t, child1.ID, chat.ID, "child1 should not remain archived")
+			require.NotEqual(t, child2.ID, chat.ID, "child2 should not remain archived")
+		}
+
+		dbParent, err := db.GetChatByID(dbauthz.AsSystemRestricted(ctx), parentChat.ID)
+		require.NoError(t, err)
+		require.False(t, dbParent.Archived, "parent should be unarchived")
+
+		dbChild1, err := db.GetChatByID(dbauthz.AsSystemRestricted(ctx), child1.ID)
+		require.NoError(t, err)
+		require.False(t, dbChild1.Archived, "child1 should be unarchived")
+
+		dbChild2, err := db.GetChatByID(dbauthz.AsSystemRestricted(ctx), child2.ID)
+		require.NoError(t, err)
+		require.False(t, dbChild2.Archived, "child2 should be unarchived")
+	})
+
 	t.Run("NotArchived", func(t *testing.T) {
 		t.Parallel()
 
@@ -3530,7 +3770,7 @@ func TestRegenerateChatTitle(t *testing.T) {
 		})
 		require.NoError(t, err)
 
-		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		otherClient := codersdk.NewExperimentalClient(otherClientRaw)
 		_, err = otherClient.RegenerateChatTitle(ctx, createdChat.ID)
 		requireSDKError(t, err, http.StatusNotFound)
@@ -3855,7 +4095,7 @@ func TestGetChatDiffStatus(t *testing.T) {
 		})
 		require.NoError(t, err)
 
-		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		otherClient := codersdk.NewExperimentalClient(otherClientRaw)
 		_, err = otherClient.GetChat(ctx, createdChat.ID)
 		requireSDKError(t, err, http.StatusNotFound)
@@ -4088,7 +4328,7 @@ func TestGetChatDiffContents(t *testing.T) {
 		})
 		require.NoError(t, err)
 
-		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		otherClient := codersdk.NewExperimentalClient(otherClientRaw)
 		_, err = otherClient.GetChatDiffContents(ctx, createdChat.ID)
 		requireSDKError(t, err, http.StatusNotFound)
@@ -4884,7 +5124,7 @@ func TestGetChatFile(t *testing.T) {
 		uploaded, err := client.UploadChatFile(ctx, firstUser.OrganizationID, "image/png", "test.png", bytes.NewReader(data))
 		require.NoError(t, err)
 
-		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID)
+		otherClientRaw, _ := coderdtest.CreateAnotherUser(t, client.Client, firstUser.OrganizationID, rbac.RoleAgentsAccess())
 		otherClient := codersdk.NewExperimentalClient(otherClientRaw)
 		_, _, err = otherClient.GetChatFile(ctx, uploaded.ID)
 		requireSDKError(t, err, http.StatusNotFound)

coderd/rbac/object_gen.go

@@ -82,6 +82,16 @@ var (
 		Type: "chat",
 	}
 
+	// ResourceChatAutomation
+	// Valid Actions
+	//  - "ActionCreate" :: create a chat automation
+	//  - "ActionDelete" :: delete a chat automation
+	//  - "ActionRead" :: read chat automation configuration
+	//  - "ActionUpdate" :: update a chat automation
+	ResourceChatAutomation = Object{
+		Type: "chat_automation",
+	}
+
 	// ResourceConnectionLog
 	// Valid Actions
 	//  - "ActionRead" :: read connection logs
@@ -440,6 +450,7 @@ func AllResources() []Objecter {
 		ResourceAuditLog,
 		ResourceBoundaryUsage,
 		ResourceChat,
+		ResourceChatAutomation,
 		ResourceConnectionLog,
 		ResourceCryptoKey,
 		ResourceDebugInfo,

coderd/rbac/policy/policy.go

@@ -84,6 +84,13 @@ var chatActions = map[Action]ActionDefinition{
 	ActionDelete: "delete a chat",
 }
 
+var chatAutomationActions = map[Action]ActionDefinition{
+	ActionCreate: "create a chat automation",
+	ActionRead:   "read chat automation configuration",
+	ActionUpdate: "update a chat automation",
+	ActionDelete: "delete a chat automation",
+}
+
 // RBACPermissions is indexed by the type
 var RBACPermissions = map[string]PermissionDefinition{
 	// Wildcard is every object, and the action "*" provides all actions.
@@ -113,6 +120,9 @@ var RBACPermissions = map[string]PermissionDefinition{
 	"chat": {
 		Actions: chatActions,
 	},
+	"chat_automation": {
+		Actions: chatAutomationActions,
+	},
 	// Dormant workspaces have the same perms as workspaces.
 	"workspace_dormant": {
 		Actions: workspaceActions,

coderd/rbac/roles.go

@@ -21,6 +21,7 @@ const (
 	templateAdmin string = "template-admin"
 	userAdmin     string = "user-admin"
 	auditor       string = "auditor"
+	agentsAccess  string = "agents-access"
 	// customSiteRole is a placeholder for all custom site roles.
 	// This is used for what roles can assign other roles.
 	// TODO: Make this more dynamic to allow other roles to grant.
@@ -142,6 +143,7 @@ func RoleTemplateAdmin() RoleIdentifier { return RoleIdentifier{Name: templateAd
 func RoleUserAdmin() RoleIdentifier     { return RoleIdentifier{Name: userAdmin} }
 func RoleMember() RoleIdentifier        { return RoleIdentifier{Name: member} }
 func RoleAuditor() RoleIdentifier       { return RoleIdentifier{Name: auditor} }
+func RoleAgentsAccess() RoleIdentifier  { return RoleIdentifier{Name: agentsAccess} }
 
 func RoleOrgAdmin() string {
 	return orgAdmin
@@ -316,7 +318,7 @@ func ReloadBuiltinRoles(opts *RoleOptions) {
 			denyPermissions...,
 		),
 		User: append(
-			allPermsExcept(ResourceWorkspaceDormant, ResourcePrebuiltWorkspace, ResourceWorkspace, ResourceUser, ResourceOrganizationMember, ResourceOrganizationMember, ResourceBoundaryUsage, ResourceAibridgeInterception),
+			allPermsExcept(ResourceWorkspaceDormant, ResourcePrebuiltWorkspace, ResourceWorkspace, ResourceUser, ResourceOrganizationMember, ResourceBoundaryUsage, ResourceAibridgeInterception, ResourceChat),
 			Permissions(map[string][]policy.Action{
 				// Users cannot do create/update/delete on themselves, but they
 				// can read their own details.
@@ -402,6 +404,21 @@ func ReloadBuiltinRoles(opts *RoleOptions) {
 		ByOrgID: map[string]OrgPermissions{},
 	}.withCachedRegoValue()
 
+	agentsAccessRole := Role{
+		Identifier:  RoleAgentsAccess(),
+		DisplayName: "Coder Agents User",
+		Site:        []Permission{},
+		User: Permissions(map[string][]policy.Action{
+			ResourceChat.Type: {
+				policy.ActionCreate,
+				policy.ActionRead,
+				policy.ActionUpdate,
+				policy.ActionDelete,
+			},
+		}),
+		ByOrgID: map[string]OrgPermissions{},
+	}.withCachedRegoValue()
+
 	builtInRoles = map[string]func(orgID uuid.UUID) Role{
 		// admin grants all actions to all resources.
 		owner: func(_ uuid.UUID) Role {
@@ -428,6 +445,13 @@ func ReloadBuiltinRoles(opts *RoleOptions) {
 			return userAdminRole
 		},
 
+		// agentsAccess grants all actions on chat resources owned
+		// by the user. Without this role, members cannot create
+		// or interact with chats.
+		agentsAccess: func(_ uuid.UUID) Role {
+			return agentsAccessRole
+		},
+
 		// orgAdmin returns a role with all actions allows in a given
 		// organization scope.
 		orgAdmin: func(organizationID uuid.UUID) Role {
@@ -600,6 +624,7 @@ var assignRoles = map[string]map[string]bool{
 		userAdmin:               true,
 		customSiteRole:          true,
 		customOrganizationRole:  true,
+		agentsAccess:            true,
 	},
 	owner: {
 		owner:                   true,
@@ -615,10 +640,12 @@ var assignRoles = map[string]map[string]bool{
 		userAdmin:               true,
 		customSiteRole:          true,
 		customOrganizationRole:  true,
+		agentsAccess:            true,
 	},
 	userAdmin: {
-		member:    true,
-		orgMember: true,
+		member:       true,
+		orgMember:    true,
+		agentsAccess: true,
 	},
 	orgAdmin: {
 		orgAdmin:                true,
@@ -854,13 +881,20 @@ func SiteBuiltInRoles() []Role {
 	for _, roleF := range builtInRoles {
 		// Must provide some non-nil uuid to filter out org roles.
 		role := roleF(uuid.New())
-		if !role.Identifier.IsOrgRole() {
+		if !role.Identifier.IsOrgRole() && role.Identifier != RoleAgentsAccess() {
 			roles = append(roles, role)
 		}
 	}
 	return roles
 }
 
+// AgentsAccessRole returns the agents-access role for use by callers
+// that need to include it conditionally (e.g. when the agents
+// experiment is enabled).
+func AgentsAccessRole() Role {
+	return builtInRoles[agentsAccess](uuid.Nil)
+}
+
 // ChangeRoleSet is a helper function that finds the difference of 2 sets of
 // roles. When setting a user's new roles, it is equivalent to adding and
 // removing roles. This set determines the changes, so that the appropriate

coderd/rbac/roles_test.go

@@ -49,6 +49,11 @@ func TestBuiltInRoles(t *testing.T) {
 			require.NoError(t, r.Valid(), "invalid role")
 		})
 	}
+
+	t.Run("agents-access", func(t *testing.T) {
+		t.Parallel()
+		require.NoError(t, rbac.AgentsAccessRole().Valid(), "invalid role")
+	})
 }
 
 // permissionGranted checks whether a permission list contains a
@@ -199,6 +204,7 @@ func TestRolePermissions(t *testing.T) {
 	orgUserAdmin := authSubject{Name: "org_user_admin", Actor: rbac.Subject{ID: templateAdminID.String(), Roles: rbac.RoleIdentifiers{rbac.RoleMember(), rbac.ScopedRoleOrgUserAdmin(orgID)}, Scope: rbac.ScopeAll}.WithCachedASTValue()}
 	orgTemplateAdmin := authSubject{Name: "org_template_admin", Actor: rbac.Subject{ID: userAdminID.String(), Roles: rbac.RoleIdentifiers{rbac.RoleMember(), rbac.ScopedRoleOrgTemplateAdmin(orgID)}, Scope: rbac.ScopeAll}.WithCachedASTValue()}
 	orgAdminBanWorkspace := authSubject{Name: "org_admin_workspace_ban", Actor: rbac.Subject{ID: adminID.String(), Roles: rbac.RoleIdentifiers{rbac.RoleMember(), rbac.ScopedRoleOrgAdmin(orgID), rbac.ScopedRoleOrgWorkspaceCreationBan(orgID)}, Scope: rbac.ScopeAll}.WithCachedASTValue()}
+	agentsAccessUser := authSubject{Name: "chat_access", Actor: rbac.Subject{ID: currentUser.String(), Roles: rbac.RoleIdentifiers{rbac.RoleMember(), rbac.RoleAgentsAccess()}, Scope: rbac.ScopeAll}.WithCachedASTValue()}
 	setOrgNotMe := authSubjectSet{orgAdmin, orgAuditor, orgUserAdmin, orgTemplateAdmin}
 
 	otherOrgAdmin := authSubject{Name: "org_admin_other", Actor: rbac.Subject{ID: uuid.NewString(), Roles: rbac.RoleIdentifiers{rbac.RoleMember(), rbac.ScopedRoleOrgAdmin(otherOrg)}, Scope: rbac.ScopeAll}.WithCachedASTValue()}
@@ -210,7 +216,7 @@ func TestRolePermissions(t *testing.T) {
 	// requiredSubjects are required to be asserted in each test case. This is
 	// to make sure one is not forgotten.
 	requiredSubjects := []authSubject{
-		memberMe, owner,
+		memberMe, owner, agentsAccessUser,
 		orgAdmin, otherOrgAdmin, orgAuditor, orgUserAdmin, orgTemplateAdmin,
 		templateAdmin, userAdmin, otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 	}
@@ -233,7 +239,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead},
 			Resource: rbac.ResourceUserObject(currentUser),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true: {owner, memberMe, templateAdmin, userAdmin, orgUserAdmin, otherOrgAdmin, otherOrgUserAdmin, orgAdmin},
+				true: {owner, memberMe, agentsAccessUser, templateAdmin, userAdmin, orgUserAdmin, otherOrgAdmin, otherOrgUserAdmin, orgAdmin},
 				false: {
 					orgTemplateAdmin, orgAuditor,
 					otherOrgAuditor, otherOrgTemplateAdmin,
@@ -246,7 +252,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceUser,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, userAdmin},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin},
 			},
 		},
 		{
@@ -256,7 +262,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgTemplateAdmin, orgAdminBanWorkspace},
-				false: {setOtherOrg, memberMe, userAdmin, orgAuditor, orgUserAdmin},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, orgAuditor, orgUserAdmin},
 			},
 		},
 		{
@@ -266,7 +272,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, orgAdminBanWorkspace},
-				false: {setOtherOrg, memberMe, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -276,7 +282,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, memberMe, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor, orgAdminBanWorkspace},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor, orgAdminBanWorkspace},
 			},
 		},
 		{
@@ -286,7 +292,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.InOrg(orgID).WithOwner(policy.WildcardSymbol),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, orgUserAdmin, orgAuditor, memberMe, userAdmin, templateAdmin, orgTemplateAdmin},
+				false: {setOtherOrg, orgUserAdmin, orgAuditor, memberMe, agentsAccessUser, userAdmin, templateAdmin, orgTemplateAdmin},
 			},
 		},
 		{
@@ -296,7 +302,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -306,7 +312,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -315,7 +321,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, memberMe, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor, orgAdminBanWorkspace},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor, orgAdminBanWorkspace},
 			},
 		},
 		{
@@ -324,7 +330,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(workspaceID).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, orgAdminBanWorkspace},
-				false: {setOtherOrg, memberMe, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -337,7 +343,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner, orgAdmin, orgAdminBanWorkspace},
 				false: {
-					memberMe, setOtherOrg,
+					memberMe, agentsAccessUser, setOtherOrg,
 					templateAdmin, userAdmin,
 					orgTemplateAdmin, orgUserAdmin, orgAuditor,
 				},
@@ -354,7 +360,7 @@ func TestRolePermissions(t *testing.T) {
 				true: {},
 				false: {
 					orgAdmin, owner, setOtherOrg,
-					userAdmin, memberMe,
+					userAdmin, memberMe, agentsAccessUser,
 					templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor,
 					orgAdminBanWorkspace,
 				},
@@ -366,7 +372,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceTemplate.WithID(templateID).InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, orgUserAdmin, orgAuditor, memberMe, userAdmin},
+				false: {setOtherOrg, orgUserAdmin, orgAuditor, memberMe, agentsAccessUser, userAdmin},
 			},
 		},
 		{
@@ -375,7 +381,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceTemplate.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAuditor, orgAdmin, templateAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, orgUserAdmin, memberMe, userAdmin},
+				false: {setOtherOrg, orgUserAdmin, memberMe, agentsAccessUser, userAdmin},
 			},
 		},
 		{
@@ -386,7 +392,7 @@ func TestRolePermissions(t *testing.T) {
 			}),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, orgAuditor, orgUserAdmin, memberMe, userAdmin},
+				false: {setOtherOrg, orgAuditor, orgUserAdmin, memberMe, agentsAccessUser, userAdmin},
 			},
 		},
 		{
@@ -397,7 +403,7 @@ func TestRolePermissions(t *testing.T) {
 				true: {owner, templateAdmin},
 				// Org template admins can only read org scoped files.
 				// File scope is currently not org scoped :cry:
-				false: {setOtherOrg, orgTemplateAdmin, orgAdmin, memberMe, userAdmin, orgAuditor, orgUserAdmin},
+				false: {setOtherOrg, orgTemplateAdmin, orgAdmin, memberMe, agentsAccessUser, userAdmin, orgAuditor, orgUserAdmin},
 			},
 		},
 		{
@@ -405,7 +411,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead},
 			Resource: rbac.ResourceFile.WithID(fileID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, memberMe, templateAdmin},
+				true:  {owner, memberMe, agentsAccessUser, templateAdmin},
 				false: {setOtherOrg, setOrgNotMe, userAdmin},
 			},
 		},
@@ -415,7 +421,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOrganization,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -424,7 +430,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOrganization.WithID(orgID).InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, orgTemplateAdmin, orgUserAdmin, orgAuditor, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, orgTemplateAdmin, orgUserAdmin, orgAuditor, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -433,7 +439,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOrganization.WithID(orgID).InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgTemplateAdmin, auditor, orgAuditor, userAdmin, orgUserAdmin},
-				false: {setOtherOrg, memberMe},
+				false: {setOtherOrg, memberMe, agentsAccessUser},
 			},
 		},
 		{
@@ -442,7 +448,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAssignOrgRole,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, userAdmin, memberMe, templateAdmin},
+				false: {setOtherOrg, setOrgNotMe, userAdmin, memberMe, agentsAccessUser, templateAdmin},
 			},
 		},
 		{
@@ -451,7 +457,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAssignRole,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, userAdmin},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin},
 			},
 		},
 		{
@@ -459,7 +465,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead},
 			Resource: rbac.ResourceAssignRole,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {setOtherOrg, setOrgNotMe, owner, memberMe, templateAdmin, userAdmin},
+				true:  {setOtherOrg, setOrgNotMe, owner, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 				false: {},
 			},
 		},
@@ -469,7 +475,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAssignOrgRole.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, userAdmin, orgUserAdmin},
-				false: {setOtherOrg, memberMe, templateAdmin, orgTemplateAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, templateAdmin, orgTemplateAdmin, orgAuditor},
 			},
 		},
 		{
@@ -478,7 +484,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAssignOrgRole.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, orgUserAdmin, orgTemplateAdmin, orgAuditor, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, orgUserAdmin, orgTemplateAdmin, orgAuditor, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -487,7 +493,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAssignOrgRole.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, orgUserAdmin, userAdmin, templateAdmin},
-				false: {setOtherOrg, memberMe, orgAuditor, orgTemplateAdmin},
+				false: {setOtherOrg, memberMe, agentsAccessUser, orgAuditor, orgTemplateAdmin},
 			},
 		},
 		{
@@ -495,7 +501,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead, policy.ActionDelete, policy.ActionUpdate},
 			Resource: rbac.ResourceApiKey.WithID(apiKeyID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, memberMe},
+				true:  {owner, memberMe, agentsAccessUser},
 				false: {setOtherOrg, setOrgNotMe, templateAdmin, userAdmin},
 			},
 		},
@@ -507,7 +513,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceInboxNotification.WithID(uuid.New()).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, orgUserAdmin, orgTemplateAdmin, orgAuditor, templateAdmin, userAdmin, memberMe},
+				false: {setOtherOrg, orgUserAdmin, orgTemplateAdmin, orgAuditor, templateAdmin, userAdmin, memberMe, agentsAccessUser},
 			},
 		},
 		{
@@ -515,7 +521,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionReadPersonal, policy.ActionUpdatePersonal},
 			Resource: rbac.ResourceUserObject(currentUser),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, memberMe, userAdmin},
+				true:  {owner, memberMe, agentsAccessUser, userAdmin},
 				false: {setOtherOrg, setOrgNotMe, templateAdmin},
 			},
 		},
@@ -525,7 +531,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOrganizationMember.WithID(currentUser).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, userAdmin, orgUserAdmin},
-				false: {setOtherOrg, orgTemplateAdmin, orgAuditor, memberMe, templateAdmin},
+				false: {setOtherOrg, orgTemplateAdmin, orgAuditor, memberMe, agentsAccessUser, templateAdmin},
 			},
 		},
 		{
@@ -534,7 +540,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOrganizationMember.WithID(currentUser).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAuditor, orgAdmin, userAdmin, templateAdmin, orgUserAdmin, orgTemplateAdmin},
-				false: {memberMe, setOtherOrg},
+				false: {memberMe, agentsAccessUser, setOtherOrg},
 			},
 		},
 		{
@@ -547,7 +553,7 @@ func TestRolePermissions(t *testing.T) {
 
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgUserAdmin, orgTemplateAdmin, orgAuditor},
-				false: {setOtherOrg, memberMe, userAdmin},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin},
 			},
 		},
 		{
@@ -560,7 +566,7 @@ func TestRolePermissions(t *testing.T) {
 			}),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, userAdmin, orgUserAdmin},
-				false: {setOtherOrg, memberMe, templateAdmin, orgTemplateAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, templateAdmin, orgTemplateAdmin, orgAuditor},
 			},
 		},
 		{
@@ -573,7 +579,7 @@ func TestRolePermissions(t *testing.T) {
 			}),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
-				false: {setOtherOrg, memberMe},
+				false: {setOtherOrg, memberMe, agentsAccessUser},
 			},
 		},
 		{
@@ -582,7 +588,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceGroupMember.WithID(currentUser).InOrg(orgID).WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAuditor, orgAdmin, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin},
-				false: {setOtherOrg, memberMe},
+				false: {setOtherOrg, memberMe, agentsAccessUser},
 			},
 		},
 		{
@@ -591,7 +597,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceGroupMember.WithID(adminID).InOrg(orgID).WithOwner(adminID.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAuditor, orgAdmin, userAdmin, templateAdmin, orgTemplateAdmin, orgUserAdmin},
-				false: {setOtherOrg, memberMe},
+				false: {setOtherOrg, memberMe, agentsAccessUser},
 			},
 		},
 		{
@@ -600,7 +606,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspaceDormant.WithID(uuid.New()).InOrg(orgID).WithOwner(memberMe.Actor.ID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {orgAdmin, owner},
-				false: {setOtherOrg, userAdmin, memberMe, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, userAdmin, memberMe, agentsAccessUser, templateAdmin, orgTemplateAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -609,7 +615,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspaceDormant.WithID(uuid.New()).InOrg(orgID).WithOwner(memberMe.Actor.ID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {},
-				false: {setOtherOrg, setOrgNotMe, memberMe, userAdmin, owner, templateAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, userAdmin, owner, templateAdmin},
 			},
 		},
 		{
@@ -618,7 +624,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspace.WithID(uuid.New()).InOrg(orgID).WithOwner(memberMe.Actor.ID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, userAdmin, templateAdmin, memberMe, orgTemplateAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, userAdmin, templateAdmin, memberMe, agentsAccessUser, orgTemplateAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -627,7 +633,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourcePrebuiltWorkspace.WithID(uuid.New()).InOrg(orgID).WithOwner(database.PrebuildsSystemUserID.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin, templateAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, userAdmin, memberMe, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, userAdmin, memberMe, agentsAccessUser, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -636,7 +642,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceTask.WithID(uuid.New()).InOrg(orgID).WithOwner(memberMe.Actor.ID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgAdmin},
-				false: {setOtherOrg, userAdmin, templateAdmin, memberMe, orgTemplateAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, userAdmin, templateAdmin, memberMe, agentsAccessUser, orgTemplateAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		// Some admin style resources
@@ -646,7 +652,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceLicense,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -655,7 +661,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceDeploymentStats,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -664,7 +670,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceDeploymentConfig,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -673,7 +679,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceDebugInfo,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -682,7 +688,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceReplicas,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -691,7 +697,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceTailnetCoordinator,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -700,7 +706,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceAuditLog,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -709,7 +715,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceProvisionerDaemon.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, templateAdmin, orgAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, orgAuditor, orgUserAdmin, memberMe, userAdmin},
+				false: {setOtherOrg, orgAuditor, orgUserAdmin, memberMe, agentsAccessUser, userAdmin},
 			},
 		},
 		{
@@ -718,7 +724,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceProvisionerDaemon.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, templateAdmin, orgAdmin, orgTemplateAdmin},
-				false: {setOtherOrg, memberMe, userAdmin, orgAuditor, orgUserAdmin},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, orgAuditor, orgUserAdmin},
 			},
 		},
 		{
@@ -727,7 +733,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceProvisionerDaemon.WithOwner(currentUser.String()).InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, templateAdmin, orgTemplateAdmin, orgAdmin},
-				false: {setOtherOrg, memberMe, userAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, userAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -736,7 +742,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceProvisionerJobs.InOrg(orgID),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner, orgTemplateAdmin, orgAdmin},
-				false: {setOtherOrg, memberMe, templateAdmin, userAdmin, orgUserAdmin, orgAuditor},
+				false: {setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin, orgUserAdmin, orgAuditor},
 			},
 		},
 		{
@@ -745,7 +751,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceSystem,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -754,7 +760,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOauth2App,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -762,7 +768,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead},
 			Resource: rbac.ResourceOauth2App,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, setOrgNotMe, setOtherOrg, memberMe, templateAdmin, userAdmin},
+				true:  {owner, setOrgNotMe, setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 				false: {},
 			},
 		},
@@ -772,7 +778,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOauth2AppSecret,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOrgNotMe, setOtherOrg, memberMe, templateAdmin, userAdmin},
+				false: {setOrgNotMe, setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -781,7 +787,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceOauth2AppCodeToken,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOrgNotMe, setOtherOrg, memberMe, templateAdmin, userAdmin},
+				false: {setOrgNotMe, setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -790,7 +796,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceWorkspaceProxy,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOrgNotMe, setOtherOrg, memberMe, templateAdmin, userAdmin},
+				false: {setOrgNotMe, setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -798,7 +804,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead},
 			Resource: rbac.ResourceWorkspaceProxy,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, setOrgNotMe, setOtherOrg, memberMe, templateAdmin, userAdmin},
+				true:  {owner, setOrgNotMe, setOtherOrg, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 				false: {},
 			},
 		},
@@ -809,7 +815,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead, policy.ActionUpdate},
 			Resource: rbac.ResourceNotificationPreference.WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true: {memberMe, owner},
+				true: {memberMe, agentsAccessUser, owner},
 				false: {
 					userAdmin, orgUserAdmin, templateAdmin,
 					orgAuditor, orgTemplateAdmin,
@@ -826,7 +832,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner},
 				false: {
-					memberMe, userAdmin, orgUserAdmin, templateAdmin,
+					memberMe, agentsAccessUser, userAdmin, orgUserAdmin, templateAdmin,
 					orgAuditor, orgTemplateAdmin,
 					otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 					orgAdmin, otherOrgAdmin,
@@ -840,7 +846,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner},
 				false: {
-					memberMe,
+					memberMe, agentsAccessUser,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -858,7 +864,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner},
 				false: {
-					memberMe, templateAdmin, orgUserAdmin, userAdmin,
+					memberMe, agentsAccessUser, templateAdmin, orgUserAdmin, userAdmin,
 					orgAdmin, orgAuditor, orgTemplateAdmin,
 					otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 					otherOrgAdmin,
@@ -871,7 +877,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead, policy.ActionDelete},
 			Resource: rbac.ResourceWebpushSubscription.WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true:  {owner, memberMe},
+				true:  {owner, memberMe, agentsAccessUser},
 				false: {orgAdmin, otherOrgAdmin, orgAuditor, otherOrgAuditor, templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin, userAdmin, orgUserAdmin, otherOrgUserAdmin},
 			},
 		},
@@ -883,7 +889,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner, userAdmin, orgAdmin, otherOrgAdmin, orgUserAdmin, otherOrgUserAdmin},
 				false: {
-					memberMe, templateAdmin,
+					memberMe, agentsAccessUser, templateAdmin,
 					orgTemplateAdmin, orgAuditor,
 					otherOrgAuditor, otherOrgTemplateAdmin,
 				},
@@ -896,7 +902,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner, templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin, orgAdmin, otherOrgAdmin},
 				false: {
-					userAdmin, memberMe,
+					userAdmin, memberMe, agentsAccessUser,
 					orgAuditor, orgUserAdmin,
 					otherOrgAuditor, otherOrgUserAdmin,
 				},
@@ -909,7 +915,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner, orgAdmin, otherOrgAdmin},
 				false: {
-					memberMe, userAdmin, templateAdmin,
+					memberMe, agentsAccessUser, userAdmin, templateAdmin,
 					orgAuditor, orgUserAdmin, orgTemplateAdmin,
 					otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 				},
@@ -921,7 +927,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceCryptoKey,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -932,7 +938,7 @@ func TestRolePermissions(t *testing.T) {
 				true: {owner, orgAdmin, orgUserAdmin, userAdmin},
 				false: {
 					otherOrgAdmin,
-					memberMe, templateAdmin,
+					memberMe, agentsAccessUser, templateAdmin,
 					orgAuditor, orgTemplateAdmin,
 					otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 				},
@@ -947,7 +953,7 @@ func TestRolePermissions(t *testing.T) {
 				false: {
 					orgAdmin, orgUserAdmin,
 					otherOrgAdmin,
-					memberMe, templateAdmin,
+					memberMe, agentsAccessUser, templateAdmin,
 					orgAuditor, orgTemplateAdmin,
 					otherOrgAuditor, otherOrgUserAdmin, otherOrgTemplateAdmin,
 				},
@@ -960,7 +966,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner},
 				false: {
-					memberMe,
+					memberMe, agentsAccessUser,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -975,7 +981,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner},
 				false: {
-					memberMe,
+					memberMe, agentsAccessUser,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -989,7 +995,7 @@ func TestRolePermissions(t *testing.T) {
 			Resource: rbac.ResourceConnectionLog,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true:  {owner},
-				false: {setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		// Only the user themselves can access their own secrets — no one else.
@@ -998,7 +1004,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
 			Resource: rbac.ResourceUserSecret.WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true: {memberMe},
+				true: {memberMe, agentsAccessUser},
 				false: {
 					owner, orgAdmin,
 					otherOrgAdmin, orgAuditor, orgUserAdmin, orgTemplateAdmin,
@@ -1014,7 +1020,7 @@ func TestRolePermissions(t *testing.T) {
 				true: {},
 				false: {
 					owner,
-					memberMe,
+					memberMe, agentsAccessUser,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -1028,7 +1034,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionUpdate},
 			Resource: rbac.ResourceAibridgeInterception.WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true: {owner, memberMe},
+				true: {owner, memberMe, agentsAccessUser},
 				false: {
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
@@ -1045,7 +1051,7 @@ func TestRolePermissions(t *testing.T) {
 			AuthorizeMap: map[bool][]hasAuthSubjects{
 				true: {owner, auditor},
 				false: {
-					memberMe,
+					memberMe, agentsAccessUser,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -1058,7 +1064,7 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
 			Resource: rbac.ResourceBoundaryUsage,
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				false: {owner, setOtherOrg, setOrgNotMe, memberMe, templateAdmin, userAdmin},
+				false: {owner, setOtherOrg, setOrgNotMe, memberMe, agentsAccessUser, templateAdmin, userAdmin},
 			},
 		},
 		{
@@ -1066,8 +1072,9 @@ func TestRolePermissions(t *testing.T) {
 			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
 			Resource: rbac.ResourceChat.WithOwner(currentUser.String()),
 			AuthorizeMap: map[bool][]hasAuthSubjects{
-				true: {owner, memberMe},
+				true: {owner, agentsAccessUser},
 				false: {
+					memberMe,
 					orgAdmin, otherOrgAdmin,
 					orgAuditor, otherOrgAuditor,
 					templateAdmin, orgTemplateAdmin, otherOrgTemplateAdmin,
@@ -1075,8 +1082,20 @@ func TestRolePermissions(t *testing.T) {
 				},
 			},
 		},
+		{
+			// Chat automations are admin-managed. Regular org
+			// members cannot manage automations even if they
+			// are the owner. The owner_id field is for audit
+			// tracking, not RBAC grants.
+			Name:     "ChatAutomation",
+			Actions:  []policy.Action{policy.ActionCreate, policy.ActionRead, policy.ActionUpdate, policy.ActionDelete},
+			Resource: rbac.ResourceChatAutomation.InOrg(orgID).WithOwner(currentUser.String()),
+			AuthorizeMap: map[bool][]hasAuthSubjects{
+				true:  {owner, orgAdmin},
+				false: {setOtherOrg, memberMe, agentsAccessUser, orgAuditor, orgUserAdmin, orgTemplateAdmin, templateAdmin, userAdmin},
+			},
+		},
 	}
-
 	// Build coverage set from test case definitions statically,
 	// so we don't need shared mutable state during execution.
 	// This allows subtests to run in parallel.
@@ -1217,7 +1236,6 @@ func TestListRoles(t *testing.T) {
 		"user-admin",
 	},
 		siteRoleNames)
-
 	orgID := uuid.New()
 	orgRoles := rbac.OrganizationRoles(orgID)
 	orgRoleNames := make([]string, 0, len(orgRoles))

coderd/rbac/scopes_constants_gen.go

@@ -32,6 +32,10 @@ const (
 	ScopeChatDelete                          ScopeName = "chat:delete"
 	ScopeChatRead                            ScopeName = "chat:read"
 	ScopeChatUpdate                          ScopeName = "chat:update"
+	ScopeChatAutomationCreate                ScopeName = "chat_automation:create"
+	ScopeChatAutomationDelete                ScopeName = "chat_automation:delete"
+	ScopeChatAutomationRead                  ScopeName = "chat_automation:read"
+	ScopeChatAutomationUpdate                ScopeName = "chat_automation:update"
 	ScopeConnectionLogRead                   ScopeName = "connection_log:read"
 	ScopeConnectionLogUpdate                 ScopeName = "connection_log:update"
 	ScopeCryptoKeyCreate                     ScopeName = "crypto_key:create"
@@ -196,6 +200,10 @@ func (e ScopeName) Valid() bool {
 		ScopeChatDelete,
 		ScopeChatRead,
 		ScopeChatUpdate,
+		ScopeChatAutomationCreate,
+		ScopeChatAutomationDelete,
+		ScopeChatAutomationRead,
+		ScopeChatAutomationUpdate,
 		ScopeConnectionLogRead,
 		ScopeConnectionLogUpdate,
 		ScopeCryptoKeyCreate,
@@ -361,6 +369,10 @@ func AllScopeNameValues() []ScopeName {
 		ScopeChatDelete,
 		ScopeChatRead,
 		ScopeChatUpdate,
+		ScopeChatAutomationCreate,
+		ScopeChatAutomationDelete,
+		ScopeChatAutomationRead,
+		ScopeChatAutomationUpdate,
 		ScopeConnectionLogRead,
 		ScopeConnectionLogUpdate,
 		ScopeCryptoKeyCreate,

coderd/roles.go

@@ -5,6 +5,7 @@ import (
 
 	"github.com/google/uuid"
 
+	"github.com/coder/coder/v2/buildinfo"
 	"github.com/coder/coder/v2/coderd/database"
 	"github.com/coder/coder/v2/coderd/database/db2sdk"
 	"github.com/coder/coder/v2/coderd/httpapi"
@@ -43,7 +44,16 @@ func (api *API) AssignableSiteRoles(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	httpapi.Write(ctx, rw, http.StatusOK, assignableRoles(actorRoles.Roles, rbac.SiteBuiltInRoles(), dbCustomRoles))
+	siteRoles := rbac.SiteBuiltInRoles()
+	// Include the agents-access role only when the agents
+	// experiment is enabled or this is a dev build, matching
+	// the RequireExperimentWithDevBypass gate on chat routes.
+	if api.Experiments.Enabled(codersdk.ExperimentAgents) || buildinfo.IsDev() {
+		siteRoles = append(siteRoles, rbac.AgentsAccessRole())
+	}
+
+	httpapi.Write(ctx, rw, http.StatusOK,
+		assignableRoles(actorRoles.Roles, siteRoles, dbCustomRoles))
 }
 
 // assignableOrgRoles returns all org wide roles that can be assigned.

coderd/x/chatd/chatd.go

@@ -1244,32 +1244,90 @@ func (p *Server) EditMessage(
 	return result, nil
 }
 
-// ArchiveChat archives a chat and all descendants, then broadcasts a deleted event.
+// ArchiveChat archives a chat family and broadcasts deleted events for each
+// affected chat so watching clients converge without a full refetch. If the
+// target chat is pending or running, it first transitions the chat back to
+// waiting so active processing stops before the archive is broadcast.
 func (p *Server) ArchiveChat(ctx context.Context, chat database.Chat) error {
 	if chat.ID == uuid.Nil {
 		return xerrors.New("chat_id is required")
 	}
 
-	if err := p.db.ArchiveChatByID(ctx, chat.ID); err != nil {
-		return xerrors.Errorf("archive chat: %w", err)
+	statusChat := chat
+	interrupted := false
+	var archivedChats []database.Chat
+	if err := p.db.InTx(func(tx database.Store) error {
+		lockedChat, err := tx.GetChatByIDForUpdate(ctx, chat.ID)
+		if err != nil {
+			return xerrors.Errorf("lock chat for archive: %w", err)
+		}
+		statusChat = lockedChat
+
+		// We do not call setChatWaiting here because it intentionally preserves
+		// pending chats so queued-message promotion can win. Archiving is a
+		// harder stop: both pending and running chats must transition to waiting.
+		if lockedChat.Status == database.ChatStatusPending || lockedChat.Status == database.ChatStatusRunning {
+			statusChat, err = tx.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
+				ID:          chat.ID,
+				Status:      database.ChatStatusWaiting,
+				WorkerID:    uuid.NullUUID{},
+				StartedAt:   sql.NullTime{},
+				HeartbeatAt: sql.NullTime{},
+				LastError:   sql.NullString{},
+			})
+			if err != nil {
+				return xerrors.Errorf("set chat waiting before archive: %w", err)
+			}
+			interrupted = true
+		}
+
+		archivedChats, err = tx.ArchiveChatByID(ctx, chat.ID)
+		if err != nil {
+			return xerrors.Errorf("archive chat: %w", err)
+		}
+		return nil
+	}, nil); err != nil {
+		return err
 	}
 
-	p.publishChatPubsubEvent(chat, coderdpubsub.ChatEventKindDeleted, nil)
+	if interrupted {
+		p.publishStatus(chat.ID, statusChat.Status, statusChat.WorkerID)
+		p.publishChatPubsubEvent(statusChat, coderdpubsub.ChatEventKindStatusChange, nil)
+	}
+
+	p.publishChatPubsubEvents(archivedChats, coderdpubsub.ChatEventKindDeleted)
 	return nil
 }
 
-// UnarchiveChat unarchives a chat and publishes a created event so sidebar
-// clients are notified that the chat has reappeared.
+// UnarchiveChat unarchives a chat family and publishes created events for
+// each affected chat so watching clients see every chat that reappeared.
 func (p *Server) UnarchiveChat(ctx context.Context, chat database.Chat) error {
 	if chat.ID == uuid.Nil {
 		return xerrors.New("chat_id is required")
 	}
 
-	if err := p.db.UnarchiveChatByID(ctx, chat.ID); err != nil {
-		return xerrors.Errorf("unarchive chat: %w", err)
+	return p.applyChatLifecycleTransition(
+		ctx,
+		chat.ID,
+		"unarchive",
+		coderdpubsub.ChatEventKindCreated,
+		p.db.UnarchiveChatByID,
+	)
+}
+
+func (p *Server) applyChatLifecycleTransition(
+	ctx context.Context,
+	chatID uuid.UUID,
+	action string,
+	kind coderdpubsub.ChatEventKind,
+	transition func(context.Context, uuid.UUID) ([]database.Chat, error),
+) error {
+	updatedChats, err := transition(ctx, chatID)
+	if err != nil {
+		return xerrors.Errorf("%s chat: %w", action, err)
 	}
 
-	p.publishChatPubsubEvent(chat, coderdpubsub.ChatEventKindCreated, nil)
+	p.publishChatPubsubEvents(updatedChats, kind)
 	return nil
 }
 
@@ -3099,6 +3157,13 @@ func (p *Server) publishChatStreamNotify(chatID uuid.UUID, notify coderdpubsub.C
 	}
 }
 
+// publishChatPubsubEvents broadcasts a lifecycle event for each affected chat.
+func (p *Server) publishChatPubsubEvents(chats []database.Chat, kind coderdpubsub.ChatEventKind) {
+	for _, chat := range chats {
+		p.publishChatPubsubEvent(chat, kind, nil)
+	}
+}
+
 // publishChatPubsubEvent broadcasts a chat lifecycle event via PostgreSQL
 // pubsub so that all replicas can push updates to watching clients.
 func (p *Server) publishChatPubsubEvent(chat database.Chat, kind coderdpubsub.ChatEventKind, diffStatus *codersdk.ChatDiffStatus) {
@@ -3447,7 +3512,25 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 	chatCtx, cancel := context.WithCancelCause(ctx)
 	defer cancel(nil)
 
-	controlCancel := p.subscribeChatControl(chatCtx, chat.ID, cancel, logger)
+	// Gate the control subscriber behind a channel that is closed
+	// after we publish "running" status. This prevents stale
+	// pubsub notifications (e.g. the "pending" notification from
+	// SendMessage that triggered this processing) from
+	// interrupting us before we start work. Due to async
+	// PostgreSQL NOTIFY delivery, a notification published before
+	// subscribeChatControl registers its queue can still arrive
+	// after registration.
+	controlArmed := make(chan struct{})
+	gatedCancel := func(cause error) {
+		select {
+		case <-controlArmed:
+			cancel(cause)
+		default:
+			logger.Debug(ctx, "ignoring control notification before armed")
+		}
+	}
+
+	controlCancel := p.subscribeChatControl(chatCtx, chat.ID, gatedCancel, logger)
 	defer func() {
 		if controlCancel != nil {
 			controlCancel()
@@ -3508,6 +3591,12 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 		Valid: true,
 	})
 
+	// Arm the control subscriber. Closing the channel is a
+	// happens-before guarantee in the Go memory model — any
+	// notification dispatched after this point will correctly
+	// interrupt processing.
+	close(controlArmed)
+
 	// Determine the final status and last error to set when we're done.
 	status := database.ChatStatusWaiting
 	wasInterrupted := false
@@ -3563,9 +3652,10 @@ func (p *Server) processChat(ctx context.Context, chat database.Chat) {
 			// the worker and let the processor pick it back up.
 			if latestChat.Status == database.ChatStatusPending {
 				status = database.ChatStatusPending
-			} else if status == database.ChatStatusWaiting {
+			} else if status == database.ChatStatusWaiting && !latestChat.Archived {
 				// Queued messages were already admitted through SendMessage,
-				// so auto-promotion only preserves FIFO order here.
+				// so auto-promotion only preserves FIFO order here. Archived
+				// chats skip promotion so archiving behaves like a hard stop.
 				var promoteErr error
 				promotedMessage, remainingQueuedMessages, shouldPublishQueueUpdate, promoteErr = p.tryAutoPromoteQueuedMessage(cleanupCtx, tx, latestChat)
 				if promoteErr != nil {
@@ -4970,9 +5060,25 @@ func (p *Server) persistInstructionFiles(
 			chatprompt.CurrentContentVersion,
 		))
 		_, _ = p.db.InsertChatMessages(ctx, msgParams)
+		// Update the cache column: persist skills if any
+		// exist, or clear to NULL so stale data from a
+		// previous agent doesn't linger.
+		if len(discoveredSkills) > 0 {
+			skillParts := make([]codersdk.ChatMessagePart, 0, len(discoveredSkills))
+			for _, s := range discoveredSkills {
+				skillParts = append(skillParts, codersdk.ChatMessagePart{
+					Type:               codersdk.ChatMessagePartTypeSkill,
+					SkillName:          s.Name,
+					SkillDescription:   s.Description,
+					ContextFileAgentID: uuid.NullUUID{UUID: agent.ID, Valid: true},
+				})
+			}
+			p.updateLastInjectedContext(ctx, chat.ID, skillParts)
+		} else {
+			p.updateLastInjectedContext(ctx, chat.ID, nil)
+		}
 		return "", discoveredSkills, nil
 	}
-
 	// Build context-file parts (one per instruction file) and
 	// skill parts (one per discovered skill).
 	parts := make([]codersdk.ChatMessagePart, 0, len(sections)+len(discoveredSkills))
@@ -5015,6 +5121,15 @@ func (p *Server) persistInstructionFiles(
 	if _, err := p.db.InsertChatMessages(ctx, msgParams); err != nil {
 		return "", nil, xerrors.Errorf("persist instruction files: %w", err)
 	}
+	// Build stripped copies for the cache column so internal
+	// fields (full file content, OS, directory, skill paths)
+	// are never persisted or returned to API clients.
+	stripped := make([]codersdk.ChatMessagePart, len(parts))
+	copy(stripped, parts)
+	for i := range stripped {
+		stripped[i].StripInternal()
+	}
+	p.updateLastInjectedContext(ctx, chat.ID, stripped)
 
 	// Return the formatted instruction text and discovered skills
 	// so the caller can inject them into this turn's prompt (since
@@ -5022,6 +5137,35 @@ func (p *Server) persistInstructionFiles(
 	return formatSystemInstructions(agent.OperatingSystem, directory, sections), discoveredSkills, nil
 }
 
+// updateLastInjectedContext persists the injected context
+// parts (AGENTS.md files and skills) on the chat row so they
+// are directly queryable without scanning messages. This is
+// best-effort — a failure here is logged but does not block
+// the turn.
+func (p *Server) updateLastInjectedContext(ctx context.Context, chatID uuid.UUID, parts []codersdk.ChatMessagePart) {
+	param := pqtype.NullRawMessage{Valid: false}
+	if parts != nil {
+		raw, err := json.Marshal(parts)
+		if err != nil {
+			p.logger.Warn(ctx, "failed to marshal injected context",
+				slog.F("chat_id", chatID),
+				slog.Error(err),
+			)
+			return
+		}
+		param = pqtype.NullRawMessage{RawMessage: raw, Valid: true}
+	}
+	if _, err := p.db.UpdateChatLastInjectedContext(ctx, database.UpdateChatLastInjectedContextParams{
+		ID:                  chatID,
+		LastInjectedContext: param,
+	}); err != nil {
+		p.logger.Warn(ctx, "failed to update injected context",
+			slog.F("chat_id", chatID),
+			slog.Error(err),
+		)
+	}
+}
+
 // resolveUserCompactionThreshold looks up the user's per-model
 // compaction threshold override. Returns the override value and
 // true if one exists and is valid, or 0 and false otherwise.

coderd/x/chatd/chatd_internal_test.go

@@ -484,6 +484,32 @@ func TestPersistInstructionFilesIncludesAgentMetadata(t *testing.T) {
 		agentID,
 	).Return(workspaceAgent, nil).Times(1)
 	db.EXPECT().InsertChatMessages(gomock.Any(), gomock.Any()).Return(nil, nil).AnyTimes()
+	db.EXPECT().UpdateChatLastInjectedContext(gomock.Any(),
+		gomock.Cond(func(x any) bool {
+			arg, ok := x.(database.UpdateChatLastInjectedContextParams)
+			if !ok || arg.ID != chat.ID {
+				return false
+			}
+			if !arg.LastInjectedContext.Valid {
+				return false
+			}
+			var parts []codersdk.ChatMessagePart
+			if err := json.Unmarshal(arg.LastInjectedContext.RawMessage, &parts); err != nil {
+				return false
+			}
+			// Expect at least one context-file part for the
+			// working-directory AGENTS.md, with internal fields
+			// stripped (no content, OS, or directory).
+			for _, p := range parts {
+				if p.Type == codersdk.ChatMessagePartTypeContextFile && p.ContextFilePath != "" {
+					return p.ContextFileContent == "" &&
+						p.ContextFileOS == "" &&
+						p.ContextFileDirectory == ""
+				}
+			}
+			return false
+		}),
+	).Return(database.Chat{}, nil).Times(1)
 
 	conn := agentconnmock.NewMockAgentConn(ctrl)
 	conn.EXPECT().SetExtraHeaders(gomock.Any()).Times(1)
@@ -569,6 +595,247 @@ func TestPersistInstructionFilesSkipsSentinelWhenWorkspaceUnavailable(t *testing
 	require.Empty(t, instruction)
 }
 
+func TestPersistInstructionFilesSentinelWithSkills(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+
+	workspaceID := uuid.New()
+	agentID := uuid.New()
+	chat := database.Chat{
+		ID: uuid.New(),
+		WorkspaceID: uuid.NullUUID{
+			UUID:  workspaceID,
+			Valid: true,
+		},
+		AgentID: uuid.NullUUID{
+			UUID:  agentID,
+			Valid: true,
+		},
+	}
+	workspaceAgent := database.WorkspaceAgent{
+		ID:                agentID,
+		OperatingSystem:   "linux",
+		Directory:         "/home/coder/project",
+		ExpandedDirectory: "/home/coder/project",
+	}
+
+	db.EXPECT().GetWorkspaceAgentByID(
+		gomock.Any(),
+		agentID,
+	).Return(workspaceAgent, nil).Times(1)
+	db.EXPECT().InsertChatMessages(gomock.Any(), gomock.Any()).Return(nil, nil).AnyTimes()
+	db.EXPECT().UpdateChatLastInjectedContext(gomock.Any(),
+		gomock.Cond(func(x any) bool {
+			arg, ok := x.(database.UpdateChatLastInjectedContextParams)
+			if !ok || arg.ID != chat.ID {
+				return false
+			}
+			if !arg.LastInjectedContext.Valid {
+				return false
+			}
+			var parts []codersdk.ChatMessagePart
+			if err := json.Unmarshal(arg.LastInjectedContext.RawMessage, &parts); err != nil {
+				return false
+			}
+			// The sentinel path should persist only skill parts
+			// with ContextFileAgentID set.
+			for _, p := range parts {
+				if p.Type == codersdk.ChatMessagePartTypeSkill &&
+					p.SkillName == "my-skill" &&
+					p.ContextFileAgentID == (uuid.NullUUID{UUID: agentID, Valid: true}) {
+					return true
+				}
+			}
+			return false
+		}),
+	).Return(database.Chat{}, nil).Times(1)
+
+	conn := agentconnmock.NewMockAgentConn(ctrl)
+	conn.EXPECT().SetExtraHeaders(gomock.Any()).Times(1)
+
+	// Home LS (.coder directory): return 404 so no home
+	// instruction file is found.
+	conn.EXPECT().LS(gomock.Any(), "",
+		gomock.Cond(func(x any) bool {
+			req, ok := x.(workspacesdk.LSRequest)
+			return ok && req.Relativity == workspacesdk.LSRelativityHome
+		}),
+	).Return(
+		workspacesdk.LSResponse{},
+		codersdk.NewTestError(404, "POST", "/api/v0/list-directory"),
+	).Times(1)
+
+	// Pwd AGENTS.md: return 404 so no working-directory
+	// instruction file is found either.
+	conn.EXPECT().ReadFile(gomock.Any(),
+		"/home/coder/project/AGENTS.md",
+		int64(0),
+		int64(maxInstructionFileBytes+1),
+	).Return(
+		nil, "",
+		codersdk.NewTestError(404, "GET", "/api/v0/read-file"),
+	).Times(1)
+
+	// Skills LS (.agents/skills directory): return one skill
+	// directory so DiscoverSkills finds it.
+	conn.EXPECT().LS(gomock.Any(), "",
+		gomock.Cond(func(x any) bool {
+			req, ok := x.(workspacesdk.LSRequest)
+			return ok && req.Relativity == workspacesdk.LSRelativityRoot
+		}),
+	).Return(workspacesdk.LSResponse{
+		Contents: []workspacesdk.LSFile{{
+			Name:               "my-skill",
+			AbsolutePathString: "/home/coder/project/.agents/skills/my-skill",
+			IsDir:              true,
+		}},
+	}, nil).Times(1)
+
+	// Skills SKILL.md ReadFile: return valid frontmatter.
+	skillContent := "---\nname: my-skill\ndescription: A test skill\n---\nSkill body"
+	conn.EXPECT().ReadFile(gomock.Any(),
+		"/home/coder/project/.agents/skills/my-skill/SKILL.md",
+		int64(0),
+		int64(64*1024+1),
+	).Return(
+		io.NopCloser(strings.NewReader(skillContent)),
+		"",
+		nil,
+	).Times(1)
+
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	server := &Server{
+		db:     db,
+		logger: logger,
+		agentConnFn: func(context.Context, uuid.UUID) (workspacesdk.AgentConn, func(), error) {
+			return conn, func() {}, nil
+		},
+	}
+
+	chatStateMu := &sync.Mutex{}
+	currentChat := chat
+	workspaceCtx := turnWorkspaceContext{
+		server:           server,
+		chatStateMu:      chatStateMu,
+		currentChat:      &currentChat,
+		loadChatSnapshot: func(context.Context, uuid.UUID) (database.Chat, error) { return database.Chat{}, nil },
+	}
+	t.Cleanup(workspaceCtx.close)
+
+	instruction, skills, err := server.persistInstructionFiles(
+		ctx,
+		chat,
+		uuid.New(),
+		workspaceCtx.getWorkspaceAgent,
+		workspaceCtx.getWorkspaceConn,
+	)
+	require.NoError(t, err)
+	// Sentinel path returns empty instruction string.
+	require.Empty(t, instruction)
+	// Skills are still discovered and returned.
+	require.Len(t, skills, 1)
+	require.Equal(t, "my-skill", skills[0].Name)
+}
+
+func TestPersistInstructionFilesSentinelNoSkillsClearsColumn(t *testing.T) {
+	t.Parallel()
+
+	ctx := context.Background()
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+
+	workspaceID := uuid.New()
+	agentID := uuid.New()
+	chat := database.Chat{
+		ID: uuid.New(),
+		WorkspaceID: uuid.NullUUID{
+			UUID:  workspaceID,
+			Valid: true,
+		},
+		AgentID: uuid.NullUUID{
+			UUID:  agentID,
+			Valid: true,
+		},
+	}
+	workspaceAgent := database.WorkspaceAgent{
+		ID:                agentID,
+		OperatingSystem:   "linux",
+		Directory:         "/home/coder/project",
+		ExpandedDirectory: "/home/coder/project",
+	}
+
+	db.EXPECT().GetWorkspaceAgentByID(
+		gomock.Any(),
+		agentID,
+	).Return(workspaceAgent, nil).Times(1)
+	db.EXPECT().InsertChatMessages(gomock.Any(), gomock.Any()).Return(nil, nil).AnyTimes()
+	db.EXPECT().UpdateChatLastInjectedContext(gomock.Any(),
+		gomock.Cond(func(x any) bool {
+			arg, ok := x.(database.UpdateChatLastInjectedContextParams)
+			if !ok || arg.ID != chat.ID {
+				return false
+			}
+			// No skills discovered, so the column should be
+			// cleared to NULL.
+			return !arg.LastInjectedContext.Valid
+		}),
+	).Return(database.Chat{}, nil).Times(1)
+
+	conn := agentconnmock.NewMockAgentConn(ctrl)
+	conn.EXPECT().SetExtraHeaders(gomock.Any()).Times(1)
+
+	// All LS calls return 404: no home .coder directory and no
+	// .agents/skills directory.
+	conn.EXPECT().LS(gomock.Any(), "", gomock.Any()).Return(
+		workspacesdk.LSResponse{},
+		codersdk.NewTestError(404, "POST", "/api/v0/list-directory"),
+	).AnyTimes()
+
+	// Pwd AGENTS.md: return 404.
+	conn.EXPECT().ReadFile(gomock.Any(),
+		"/home/coder/project/AGENTS.md",
+		int64(0),
+		int64(maxInstructionFileBytes+1),
+	).Return(
+		nil, "",
+		codersdk.NewTestError(404, "GET", "/api/v0/read-file"),
+	).Times(1)
+
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	server := &Server{
+		db:     db,
+		logger: logger,
+		agentConnFn: func(context.Context, uuid.UUID) (workspacesdk.AgentConn, func(), error) {
+			return conn, func() {}, nil
+		},
+	}
+
+	chatStateMu := &sync.Mutex{}
+	currentChat := chat
+	workspaceCtx := turnWorkspaceContext{
+		server:           server,
+		chatStateMu:      chatStateMu,
+		currentChat:      &currentChat,
+		loadChatSnapshot: func(context.Context, uuid.UUID) (database.Chat, error) { return database.Chat{}, nil },
+	}
+	t.Cleanup(workspaceCtx.close)
+
+	instruction, skills, err := server.persistInstructionFiles(
+		ctx,
+		chat,
+		uuid.New(),
+		workspaceCtx.getWorkspaceAgent,
+		workspaceCtx.getWorkspaceConn,
+	)
+	require.NoError(t, err)
+	// Sentinel path: empty instruction, no skills.
+	require.Empty(t, instruction)
+	require.Empty(t, skills)
+}
+
 func TestTurnWorkspaceContext_BindingFirstPath(t *testing.T) {
 	t.Parallel()
 
@@ -1751,3 +2018,95 @@ func chatMessageWithParts(parts []codersdk.ChatMessagePart) database.ChatMessage
 		Content: pqtype.NullRawMessage{RawMessage: raw, Valid: true},
 	}
 }
+
+// TestProcessChat_IgnoresStaleControlNotification verifies that
+// processChat is not interrupted by a "pending" notification
+// published before processing begins. This is the race that caused
+// TestOpenAIReasoningWithWebSearchRoundTripStoreFalse to flake:
+// SendMessage publishes "pending" via PostgreSQL NOTIFY, and due
+// to async delivery the notification can arrive at the control
+// subscriber after it registers but before the processor publishes
+// "running".
+func TestProcessChat_IgnoresStaleControlNotification(t *testing.T) {
+	t.Parallel()
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
+	ctrl := gomock.NewController(t)
+	db := dbmock.NewMockStore(ctrl)
+	ps := dbpubsub.NewInMemory()
+	clock := quartz.NewMock(t)
+
+	chatID := uuid.New()
+	workerID := uuid.New()
+
+	server := &Server{
+		db:                    db,
+		logger:                logger,
+		pubsub:                ps,
+		clock:                 clock,
+		workerID:              workerID,
+		chatHeartbeatInterval: time.Minute,
+		configCache:           newChatConfigCache(ctx, db, clock),
+	}
+
+	// Publish a stale "pending" notification on the control channel
+	// BEFORE processChat subscribes. In production this is the
+	// notification from SendMessage that triggered the processing.
+	staleNotify, err := json.Marshal(coderdpubsub.ChatStreamNotifyMessage{
+		Status: string(database.ChatStatusPending),
+	})
+	require.NoError(t, err)
+	err = ps.Publish(coderdpubsub.ChatStreamNotifyChannel(chatID), staleNotify)
+	require.NoError(t, err)
+
+	// Track which status processChat writes during cleanup.
+	var finalStatus database.ChatStatus
+	cleanupDone := make(chan struct{})
+
+	// The deferred cleanup in processChat runs a transaction.
+	db.EXPECT().InTx(gomock.Any(), gomock.Any()).DoAndReturn(
+		func(fn func(database.Store) error, _ *database.TxOptions) error {
+			return fn(db)
+		},
+	)
+	db.EXPECT().GetChatByIDForUpdate(gomock.Any(), chatID).Return(
+		database.Chat{ID: chatID, Status: database.ChatStatusRunning, WorkerID: uuid.NullUUID{UUID: workerID, Valid: true}}, nil,
+	)
+	db.EXPECT().UpdateChatStatus(gomock.Any(), gomock.Any()).DoAndReturn(
+		func(_ context.Context, params database.UpdateChatStatusParams) (database.Chat, error) {
+			finalStatus = params.Status
+			close(cleanupDone)
+			return database.Chat{ID: chatID, Status: params.Status}, nil
+		},
+	)
+
+	// resolveChatModel fails immediately — that's fine, we only
+	// need processChat to get past initialization without being
+	// interrupted by the stale notification.
+	db.EXPECT().GetChatModelConfigByID(gomock.Any(), gomock.Any()).Return(
+		database.ChatModelConfig{}, xerrors.New("no model configured"),
+	).AnyTimes()
+	db.EXPECT().GetEnabledChatProviders(gomock.Any()).Return(nil, nil).AnyTimes()
+	db.EXPECT().GetEnabledChatModelConfigs(gomock.Any()).Return(nil, nil).AnyTimes()
+	db.EXPECT().GetChatUsageLimitConfig(gomock.Any()).Return(
+		database.ChatUsageLimitConfig{}, sql.ErrNoRows,
+	).AnyTimes()
+	db.EXPECT().GetChatMessagesForPromptByChatID(gomock.Any(), chatID).Return(nil, nil).AnyTimes()
+
+	chat := database.Chat{ID: chatID, LastModelConfigID: uuid.New()}
+	go server.processChat(ctx, chat)
+
+	select {
+	case <-cleanupDone:
+	case <-ctx.Done():
+		t.Fatal("processChat did not complete")
+	}
+
+	// If the stale notification interrupted us, status would be
+	// "waiting" (the ErrInterrupted path). Since the gate blocked
+	// it, processChat reached runChat, which failed on model
+	// resolution → status is "error".
+	require.Equal(t, database.ChatStatusError, finalStatus,
+		"processChat should have reached runChat (error), not been interrupted (waiting)")
+}

coderd/x/chatd/chatd_test.go

@@ -297,6 +297,180 @@ func TestInterruptChatClearsWorkerInDatabase(t *testing.T) {
 	require.False(t, fromDB.WorkerID.Valid)
 }
 
+func TestArchiveChatMovesPendingChatToWaiting(t *testing.T) {
+	t.Parallel()
+
+	db, ps := dbtestutil.NewDB(t)
+	replica := newTestServer(t, db, ps, uuid.New())
+
+	ctx := testutil.Context(t, testutil.WaitLong)
+	user, model := seedChatDependencies(ctx, t, db)
+
+	chat, err := replica.CreateChat(ctx, chatd.CreateOptions{
+		OwnerID:            user.ID,
+		Title:              "archive-pending",
+		ModelConfigID:      model.ID,
+		InitialUserContent: []codersdk.ChatMessagePart{codersdk.ChatMessageText("hello")},
+	})
+	require.NoError(t, err)
+
+	chat, err = db.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
+		ID:          chat.ID,
+		Status:      database.ChatStatusPending,
+		WorkerID:    uuid.NullUUID{},
+		StartedAt:   sql.NullTime{},
+		HeartbeatAt: sql.NullTime{},
+		LastError:   sql.NullString{},
+	})
+	require.NoError(t, err)
+
+	err = replica.ArchiveChat(ctx, chat)
+	require.NoError(t, err)
+
+	fromDB, err := db.GetChatByID(ctx, chat.ID)
+	require.NoError(t, err)
+	require.Equal(t, database.ChatStatusWaiting, fromDB.Status)
+	require.False(t, fromDB.WorkerID.Valid)
+	require.False(t, fromDB.StartedAt.Valid)
+	require.False(t, fromDB.HeartbeatAt.Valid)
+	require.True(t, fromDB.Archived)
+	require.Zero(t, fromDB.PinOrder)
+}
+
+func TestArchiveChatInterruptsActiveProcessing(t *testing.T) {
+	t.Parallel()
+
+	db, ps := dbtestutil.NewDB(t)
+	ctx := testutil.Context(t, testutil.WaitLong)
+
+	streamStarted := make(chan struct{})
+	streamCanceled := make(chan struct{})
+	openAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
+		if !req.Stream {
+			return chattest.OpenAINonStreamingResponse("title")
+		}
+		chunks := make(chan chattest.OpenAIChunk, 1)
+		go func() {
+			defer close(chunks)
+			chunks <- chattest.OpenAITextChunks("partial")[0]
+			select {
+			case <-streamStarted:
+			default:
+				close(streamStarted)
+			}
+			<-req.Context().Done()
+			select {
+			case <-streamCanceled:
+			default:
+				close(streamCanceled)
+			}
+		}()
+		return chattest.OpenAIResponse{StreamingChunks: chunks}
+	})
+
+	server := newActiveTestServer(t, db, ps)
+	user, model := seedChatDependencies(ctx, t, db)
+	setOpenAIProviderBaseURL(ctx, t, db, openAIURL)
+
+	chat, err := server.CreateChat(ctx, chatd.CreateOptions{
+		OwnerID:            user.ID,
+		Title:              "archive-interrupt",
+		ModelConfigID:      model.ID,
+		InitialUserContent: []codersdk.ChatMessagePart{codersdk.ChatMessageText("hello")},
+	})
+	require.NoError(t, err)
+
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		fromDB, dbErr := db.GetChatByID(ctx, chat.ID)
+		if dbErr != nil {
+			return false
+		}
+		return fromDB.Status == database.ChatStatusRunning && fromDB.WorkerID.Valid
+	}, testutil.IntervalFast)
+
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		select {
+		case <-streamStarted:
+			return true
+		default:
+			return false
+		}
+	}, testutil.IntervalFast)
+
+	_, events, cancel, ok := server.Subscribe(ctx, chat.ID, nil, 0)
+	require.True(t, ok)
+	defer cancel()
+
+	queuedResult, err := server.SendMessage(ctx, chatd.SendMessageOptions{
+		ChatID:       chat.ID,
+		Content:      []codersdk.ChatMessagePart{codersdk.ChatMessageText("queued")},
+		BusyBehavior: chatd.SendMessageBusyBehaviorQueue,
+	})
+	require.NoError(t, err)
+	require.True(t, queuedResult.Queued)
+	require.NotNil(t, queuedResult.QueuedMessage)
+
+	err = server.ArchiveChat(ctx, chat)
+	require.NoError(t, err)
+
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		select {
+		case <-streamCanceled:
+			return true
+		default:
+			return false
+		}
+	}, testutil.IntervalFast)
+
+	gotWaitingStatus := false
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		for {
+			select {
+			case ev := <-events:
+				if ev.Type == codersdk.ChatStreamEventTypeStatus &&
+					ev.Status != nil &&
+					ev.Status.Status == codersdk.ChatStatusWaiting {
+					gotWaitingStatus = true
+					return true
+				}
+			default:
+				return gotWaitingStatus
+			}
+		}
+	}, testutil.IntervalFast)
+	require.True(t, gotWaitingStatus, "expected a waiting status event after archive")
+
+	testutil.Eventually(ctx, t, func(ctx context.Context) bool {
+		fromDB, dbErr := db.GetChatByID(ctx, chat.ID)
+		if dbErr != nil {
+			return false
+		}
+		return fromDB.Archived &&
+			fromDB.Status == database.ChatStatusWaiting &&
+			!fromDB.WorkerID.Valid &&
+			!fromDB.StartedAt.Valid &&
+			!fromDB.HeartbeatAt.Valid
+	}, testutil.IntervalFast)
+
+	queuedMessages, err := db.GetChatQueuedMessages(ctx, chat.ID)
+	require.NoError(t, err)
+	require.Len(t, queuedMessages, 1)
+	require.Equal(t, queuedResult.QueuedMessage.ID, queuedMessages[0].ID)
+
+	messages, err := db.GetChatMessagesByChatID(ctx, database.GetChatMessagesByChatIDParams{
+		ChatID:  chat.ID,
+		AfterID: 0,
+	})
+	require.NoError(t, err)
+	userMessages := 0
+	for _, msg := range messages {
+		if msg.Role == database.ChatMessageRoleUser {
+			userMessages++
+		}
+	}
+	require.Equal(t, 1, userMessages, "expected queued message to stay queued after archive")
+}
+
 func TestUpdateChatHeartbeatRequiresOwnership(t *testing.T) {
 	t.Parallel()
 
@@ -473,6 +647,11 @@ func TestSendMessageInterruptBehaviorQueuesAndInterruptsWhenBusy(t *testing.T) {
 	})
 	require.NoError(t, err)
 
+	// CreateChat calls signalWake which triggers processOnce in
+	// the background. Wait for that processing to finish so it
+	// doesn't race with the manual status update below.
+	waitForChatProcessed(ctx, t, db, chat.ID, replica)
+
 	chat, err = db.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
 		ID:          chat.ID,
 		Status:      database.ChatStatusRunning,
@@ -817,6 +996,11 @@ func TestPromoteQueuedAllowsAlreadyQueuedMessageWhenUsageLimitReached(t *testing
 	})
 	require.NoError(t, err)
 
+	// CreateChat calls signalWake which triggers processOnce in
+	// the background. Wait for that processing to finish so it
+	// doesn't race with the manual status update below.
+	waitForChatProcessed(ctx, t, db, chat.ID, replica)
+
 	chat, err = db.UpdateChatStatus(ctx, database.UpdateChatStatusParams{
 		ID:          chat.ID,
 		Status:      database.ChatStatusRunning,
@@ -879,10 +1063,6 @@ func TestPromoteQueuedAllowsAlreadyQueuedMessageWhenUsageLimitReached(t *testing
 	require.NoError(t, err)
 	require.Equal(t, database.ChatMessageRoleUser, result.PromotedMessage.Role)
 
-	chat, err = db.GetChatByID(ctx, chat.ID)
-	require.NoError(t, err)
-	require.Equal(t, database.ChatStatusPending, chat.Status)
-
 	queued, err := db.GetChatQueuedMessages(ctx, chat.ID)
 	require.NoError(t, err)
 	require.Empty(t, queued)
@@ -1709,13 +1889,9 @@ func TestSubscribeNoPubsubNoDuplicateMessageParts(t *testing.T) {
 	// subscribing, so the snapshot captures the final state.
 	// The wake signal may trigger processOnce which will fail
 	// (no LLM configured) and set the chat to error status.
-	// Poll until the chat leaves pending status, then wait for
-	// the goroutine to finish.
-	require.Eventually(t, func() bool {
-		c, err := db.GetChatByID(ctx, chat.ID)
-		return err == nil && c.Status != database.ChatStatusPending
-	}, testutil.WaitShort, testutil.IntervalFast)
-	chatd.WaitUntilIdleForTest(replica)
+	// Poll until the chat reaches a terminal state (not pending
+	// and not running), then wait for the goroutine to finish.
+	waitForChatProcessed(ctx, t, db, chat.ID, replica)
 
 	snapshot, events, cancel, ok := replica.Subscribe(ctx, chat.ID, nil, 0)
 	require.True(t, ok)
@@ -2598,6 +2774,39 @@ func TestHeartbeatNoWorkspaceNoBump(t *testing.T) {
 	require.Equal(t, 0, count, "expected no workspaces to be flushed when chat has no workspace")
 }
 
+// waitForChatProcessed waits for a wake-triggered processOnce to
+// fully complete for the given chat. It polls until the chat leaves
+// both pending and running states (meaning processChat has finished
+// its cleanup and updated the DB), then calls WaitUntilIdleForTest.
+//
+// Waiting for a terminal state (not just "not pending") avoids a
+// WaitGroup Add/Wait race: AcquireChats changes the DB status to
+// running before processOnce calls inflight.Add(1). If we only
+// waited for status != pending, we could call Wait() while Add(1)
+// hasn't happened yet.
+func waitForChatProcessed(
+	ctx context.Context,
+	t *testing.T,
+	db database.Store,
+	chatID uuid.UUID,
+	server *chatd.Server,
+) {
+	t.Helper()
+	require.Eventually(t, func() bool {
+		c, err := db.GetChatByID(ctx, chatID)
+		if err != nil {
+			return false
+		}
+		// Wait until the chat reaches a terminal state — neither
+		// pending (waiting to be acquired) nor running (being
+		// processed). This guarantees that inflight.Add(1) has
+		// already been called by processOnce.
+		return c.Status != database.ChatStatusPending &&
+			c.Status != database.ChatStatusRunning
+	}, testutil.WaitShort, testutil.IntervalFast)
+	chatd.WaitUntilIdleForTest(server)
+}
+
 func newTestServer(
 	t *testing.T,
 	db database.Store,

coderd/x/chatd/integration_test.go

@@ -1,24 +1,14 @@
 package chatd_test
 
 import (
-	"bytes"
 	"context"
-	"encoding/json"
-	"io"
-	"net/http"
-	"net/http/httptest"
 	"os"
-	"strconv"
-	"strings"
-	"sync"
-	"sync/atomic"
 	"testing"
 
 	"github.com/stretchr/testify/require"
 
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/coderd/util/ptr"
-	"github.com/coder/coder/v2/coderd/x/chatd/chattest"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/testutil"
 )
@@ -597,306 +587,3 @@ func partTypeSet(parts []codersdk.ChatMessagePart) map[codersdk.ChatMessagePartT
 	}
 	return set
 }
-
-type openAIStoreMode string
-
-const (
-	openAIStoreModeTrue  openAIStoreMode = "store_true"
-	openAIStoreModeFalse openAIStoreMode = "store_false"
-)
-
-func TestOpenAIReasoningWithWebSearchRoundTrip(t *testing.T) {
-	t.Parallel()
-	runOpenAIReasoningWithWebSearchRoundTripTest(t, openAIStoreModeTrue)
-}
-
-func TestOpenAIReasoningWithWebSearchRoundTripStoreFalse(t *testing.T) {
-	t.Parallel()
-	runOpenAIReasoningWithWebSearchRoundTripTest(t, openAIStoreModeFalse)
-}
-
-func runOpenAIReasoningWithWebSearchRoundTripTest(t *testing.T, storeMode openAIStoreMode) {
-	t.Helper()
-
-	ctx := testutil.Context(t, testutil.WaitLong)
-	store := storeMode == openAIStoreModeTrue
-
-	type capturedOpenAIRequest struct {
-		Stream             bool          `json:"stream,omitempty"`
-		Store              *bool         `json:"store,omitempty"`
-		PreviousResponseID *string       `json:"previous_response_id,omitempty"`
-		Prompt             []interface{} `json:"input,omitempty"`
-	}
-
-	var (
-		streamRequestCount atomic.Int32
-		firstReq           *capturedOpenAIRequest
-		secondReq          *capturedOpenAIRequest
-		mu                 sync.Mutex
-	)
-	upstreamOpenAIURL := chattest.NewOpenAI(t, func(req *chattest.OpenAIRequest) chattest.OpenAIResponse {
-		if !req.Stream {
-			return chattest.OpenAINonStreamingResponse("reasoning + web search title")
-		}
-
-		switch req.Header.Get("X-Request-Ordinal") {
-		case "1":
-			return chattest.OpenAIResponse{
-				ResponseID: "resp_first_test",
-				StreamingChunks: chattest.OpenAIStreamingResponse(
-					chattest.OpenAITextChunks("Here is what I found.")...,
-				).StreamingChunks,
-				Reasoning: &chattest.OpenAIReasoningItem{
-					Summary:          "thinking about the question",
-					EncryptedContent: "encrypted_data_here",
-				},
-				WebSearch: &chattest.OpenAIWebSearchCall{
-					Query: "latest AI news",
-				},
-			}
-		default:
-			return chattest.OpenAIStreamingResponse(
-				chattest.OpenAITextChunks("Follow-up answer.")...,
-			)
-		}
-	})
-	captureServer := httptest.NewServer(http.HandlerFunc(func(rw http.ResponseWriter, r *http.Request) {
-		body, err := io.ReadAll(r.Body)
-		if err != nil {
-			t.Errorf("read OpenAI request body: %v", err)
-			http.Error(rw, err.Error(), http.StatusInternalServerError)
-			return
-		}
-		_ = r.Body.Close()
-
-		if r.URL.Path == "/responses" {
-			var captured capturedOpenAIRequest
-			if err := json.Unmarshal(body, &captured); err != nil {
-				t.Errorf("decode OpenAI request body: %v", err)
-				http.Error(rw, err.Error(), http.StatusBadRequest)
-				return
-			}
-			if captured.Stream {
-				requestCount := streamRequestCount.Add(1)
-				r.Header.Set("X-Request-Ordinal", strconv.Itoa(int(requestCount)))
-
-				mu.Lock()
-				switch requestCount {
-				case 1:
-					firstReq = &captured
-				default:
-					secondReq = &captured
-				}
-				mu.Unlock()
-			}
-		}
-
-		upstreamReq, err := http.NewRequestWithContext(
-			r.Context(),
-			r.Method,
-			upstreamOpenAIURL+r.URL.RequestURI(),
-			bytes.NewReader(body),
-		)
-		if err != nil {
-			t.Errorf("create upstream OpenAI request: %v", err)
-			http.Error(rw, err.Error(), http.StatusInternalServerError)
-			return
-		}
-		upstreamReq.Header = r.Header.Clone()
-
-		resp, err := http.DefaultClient.Do(upstreamReq)
-		if err != nil {
-			t.Errorf("forward OpenAI request: %v", err)
-			http.Error(rw, err.Error(), http.StatusBadGateway)
-			return
-		}
-		defer resp.Body.Close()
-
-		for key, values := range resp.Header {
-			for _, value := range values {
-				rw.Header().Add(key, value)
-			}
-		}
-		rw.WriteHeader(resp.StatusCode)
-		if _, err := io.Copy(rw, resp.Body); err != nil {
-			t.Errorf("copy OpenAI response body: %v", err)
-		}
-	}))
-	t.Cleanup(captureServer.Close)
-	openAIURL := captureServer.URL
-
-	deploymentValues := coderdtest.DeploymentValues(t)
-	deploymentValues.Experiments = []string{string(codersdk.ExperimentAgents)}
-	client := coderdtest.New(t, &coderdtest.Options{
-		DeploymentValues: deploymentValues,
-	})
-	_ = coderdtest.CreateFirstUser(t, client)
-	expClient := codersdk.NewExperimentalClient(client)
-
-	_, err := expClient.CreateChatProvider(ctx, codersdk.CreateChatProviderConfigRequest{
-		Provider: "openai",
-		APIKey:   "test-api-key",
-		BaseURL:  openAIURL,
-	})
-	require.NoError(t, err)
-
-	contextLimit := int64(200000)
-	isDefault := true
-	reasoningEffort := "medium"
-	reasoningSummary := "auto"
-	_, err = expClient.CreateChatModelConfig(ctx, codersdk.CreateChatModelConfigRequest{
-		Provider:     "openai",
-		Model:        "o4-mini",
-		ContextLimit: &contextLimit,
-		IsDefault:    &isDefault,
-		ModelConfig: &codersdk.ChatModelCallConfig{
-			ProviderOptions: &codersdk.ChatModelProviderOptions{
-				OpenAI: &codersdk.ChatModelOpenAIProviderOptions{
-					Store:            ptr.Ref(store),
-					ReasoningEffort:  &reasoningEffort,
-					ReasoningSummary: &reasoningSummary,
-					WebSearchEnabled: ptr.Ref(true),
-				},
-			},
-		},
-	})
-	require.NoError(t, err)
-
-	t.Logf("Creating chat with reasoning + web search query (store=%t)...", store)
-	chat, err := expClient.CreateChat(ctx, codersdk.CreateChatRequest{
-		Content: []codersdk.ChatInputPart{{
-			Type: codersdk.ChatInputPartTypeText,
-			Text: "Search for the latest AI news and summarize it briefly.",
-		}},
-	})
-	require.NoError(t, err)
-
-	events, closer, err := expClient.StreamChat(ctx, chat.ID, nil)
-	require.NoError(t, err)
-	defer closer.Close()
-
-	waitForChatDone(ctx, t, events, "step 1")
-
-	chatData, err := expClient.GetChat(ctx, chat.ID)
-	require.NoError(t, err)
-	chatMsgs, err := expClient.GetChatMessages(ctx, chat.ID, nil)
-	require.NoError(t, err)
-	require.Equal(t, codersdk.ChatStatusWaiting, chatData.Status,
-		"chat should be in waiting status after step 1")
-
-	assistantMsg := findAssistantWithText(t, chatMsgs.Messages)
-	require.NotNil(t, assistantMsg,
-		"expected an assistant message with text content after step 1")
-
-	partTypes := partTypeSet(assistantMsg.Content)
-	require.Contains(t, partTypes, codersdk.ChatMessagePartTypeReasoning,
-		"assistant message should contain reasoning parts")
-	require.Contains(t, partTypes, codersdk.ChatMessagePartTypeToolCall,
-		"assistant message should contain a provider-executed web search tool call")
-	require.Contains(t, partTypes, codersdk.ChatMessagePartTypeToolResult,
-		"assistant message should contain a provider-executed web search tool result")
-	require.Contains(t, partTypes, codersdk.ChatMessagePartTypeText,
-		"assistant message should contain a text part")
-
-	var foundReasoning, foundWebSearchCall, foundText bool
-	for _, part := range assistantMsg.Content {
-		switch part.Type {
-		case codersdk.ChatMessagePartTypeReasoning:
-			// fantasy emits a leading newline when the reasoning summary part is
-			// added, so match the persisted summary text after trimming whitespace.
-			if strings.TrimSpace(part.Text) == "thinking about the question" {
-				foundReasoning = true
-			}
-		case codersdk.ChatMessagePartTypeToolCall:
-			if part.ToolName == "web_search" {
-				require.True(t, part.ProviderExecuted,
-					"web search tool-call should be marked provider-executed")
-				foundWebSearchCall = true
-			}
-		case codersdk.ChatMessagePartTypeText:
-			if part.Text == "Here is what I found." {
-				foundText = true
-			}
-		}
-	}
-	require.True(t, foundReasoning, "expected reasoning summary text to be persisted")
-	require.True(t, foundWebSearchCall, "expected persisted web_search tool call")
-	require.True(t, foundText, "expected streamed assistant text to be persisted")
-
-	t.Log("Sending follow-up message...")
-	_, err = expClient.CreateChatMessage(ctx, chat.ID, codersdk.CreateChatMessageRequest{
-		Content: []codersdk.ChatInputPart{{
-			Type: codersdk.ChatInputPartTypeText,
-			Text: "What is the follow-up takeaway?",
-		}},
-	})
-	if !store && err != nil {
-		require.NotContains(t, err.Error(),
-			"Items are not persisted when store is set to false.",
-			"follow-up should reconstruct store=false responses without stale provider item IDs")
-	}
-	require.NoError(t, err)
-
-	events2, closer2, err := expClient.StreamChat(ctx, chat.ID, nil)
-	require.NoError(t, err)
-	defer closer2.Close()
-
-	waitForChatDone(ctx, t, events2, "step 2")
-
-	chatData2, err := expClient.GetChat(ctx, chat.ID)
-	require.NoError(t, err)
-	chatMsgs2, err := expClient.GetChatMessages(ctx, chat.ID, nil)
-	require.NoError(t, err)
-	require.Equal(t, codersdk.ChatStatusWaiting, chatData2.Status,
-		"chat should be in waiting status after step 2")
-	require.Greater(t, len(chatMsgs2.Messages), len(chatMsgs.Messages),
-		"follow-up should have added more messages")
-	require.NotNil(t, findLastAssistantWithText(t, chatMsgs2.Messages),
-		"expected an assistant message with text after the follow-up")
-	require.Equal(t, int32(2), streamRequestCount.Load(),
-		"expected exactly two streamed OpenAI responses")
-
-	mu.Lock()
-	defer mu.Unlock()
-
-	require.NotNil(t, firstReq, "expected first streaming request to be captured")
-	if store {
-		require.NotNil(t, firstReq.Store, "first request should have store field")
-		require.True(t, *firstReq.Store, "store should be true")
-	} else if firstReq.Store != nil {
-		require.False(t, *firstReq.Store, "store should be false")
-	}
-
-	require.NotNil(t, secondReq, "expected second streaming request to be captured")
-	foundAssistantReplay := false
-	for _, item := range secondReq.Prompt {
-		m, ok := item.(map[string]interface{})
-		if !ok {
-			continue
-		}
-		role, _ := m["role"].(string)
-		if role == "assistant" {
-			foundAssistantReplay = true
-		}
-		if store {
-			require.NotEqual(t, "assistant", role,
-				"store=true chain-mode prompt should not replay assistant messages")
-			require.NotEqual(t, "tool", role,
-				"store=true chain-mode prompt should not replay tool messages")
-		}
-	}
-
-	if store {
-		require.NotNil(t, secondReq.PreviousResponseID,
-			"store=true follow-up should set previous_response_id")
-		require.Equal(t, "resp_first_test", *secondReq.PreviousResponseID,
-			"previous_response_id should match the first response's ID")
-	} else {
-		if secondReq.PreviousResponseID != nil {
-			require.Empty(t, *secondReq.PreviousResponseID,
-				"store=false follow-up should not set previous_response_id")
-		}
-		require.True(t, foundAssistantReplay,
-			"store=false follow-up should replay prior assistant history")
-	}
-}

codersdk/apikey_scopes_gen.go

@@ -38,6 +38,11 @@ const (
 	APIKeyScopeChatDelete                          APIKeyScope = "chat:delete"
 	APIKeyScopeChatRead                            APIKeyScope = "chat:read"
 	APIKeyScopeChatUpdate                          APIKeyScope = "chat:update"
+	APIKeyScopeChatAutomationAll                   APIKeyScope = "chat_automation:*"
+	APIKeyScopeChatAutomationCreate                APIKeyScope = "chat_automation:create"
+	APIKeyScopeChatAutomationDelete                APIKeyScope = "chat_automation:delete"
+	APIKeyScopeChatAutomationRead                  APIKeyScope = "chat_automation:read"
+	APIKeyScopeChatAutomationUpdate                APIKeyScope = "chat_automation:update"
 	APIKeyScopeCoderAll                            APIKeyScope = "coder:all"
 	APIKeyScopeCoderApikeysManageSelf              APIKeyScope = "coder:apikeys.manage_self"
 	APIKeyScopeCoderApplicationConnect             APIKeyScope = "coder:application_connect"

codersdk/chats.go

@@ -68,6 +68,11 @@ type Chat struct {
 	// the owner's read cursor, which updates on stream
 	// connect and disconnect.
 	HasUnread bool `json:"has_unread"`
+	// LastInjectedContext holds the most recently persisted
+	// injected context parts (AGENTS.md files and skills). It
+	// is updated only when context changes — first workspace
+	// attach or agent change.
+	LastInjectedContext []ChatMessagePart `json:"last_injected_context,omitempty"`
 }
 
 // ChatMessage represents a single message in a chat.

codersdk/deployment.go

@@ -3923,15 +3923,17 @@ Write out the current server config as YAML to stdout.`,
 			YAML:        "key_file",
 		},
 		{
-			Name:        "AI Bridge Proxy Domain Allowlist",
-			Description: "Comma-separated list of AI provider domains for which HTTPS traffic will be decrypted and routed through AI Bridge. Requests to other domains will be tunneled directly without decryption. Supported domains: api.anthropic.com, api.openai.com, api.individual.githubcopilot.com.",
-			Flag:        "aibridge-proxy-domain-allowlist",
-			Env:         "CODER_AIBRIDGE_PROXY_DOMAIN_ALLOWLIST",
-			Value:       &c.AI.BridgeProxyConfig.DomainAllowlist,
-			Default:     "api.anthropic.com,api.openai.com,api.individual.githubcopilot.com",
-			Hidden:      true,
-			Group:       &deploymentGroupAIBridgeProxy,
-			YAML:        "domain_allowlist",
+			Name: "AI Bridge Proxy Domain Allowlist",
+			Description: "Comma-separated list of AI provider domains for which HTTPS traffic will be decrypted and routed through AI Bridge. " +
+				"Requests to other domains will be tunneled directly without decryption. " +
+				"Supported domains: api.anthropic.com, api.openai.com, api.individual.githubcopilot.com, api.business.githubcopilot.com, api.enterprise.githubcopilot.com, chatgpt.com.",
+			Flag:    "aibridge-proxy-domain-allowlist",
+			Env:     "CODER_AIBRIDGE_PROXY_DOMAIN_ALLOWLIST",
+			Value:   &c.AI.BridgeProxyConfig.DomainAllowlist,
+			Default: "api.anthropic.com,api.openai.com,api.individual.githubcopilot.com,api.business.githubcopilot.com,api.enterprise.githubcopilot.com,chatgpt.com",
+			Hidden:  true,
+			Group:   &deploymentGroupAIBridgeProxy,
+			YAML:    "domain_allowlist",
 		},
 		{
 			Name:        "AI Bridge Proxy Upstream Proxy",

codersdk/rbacresources_gen.go

@@ -12,6 +12,7 @@ const (
 	ResourceAuditLog                      RBACResource = "audit_log"
 	ResourceBoundaryUsage                 RBACResource = "boundary_usage"
 	ResourceChat                          RBACResource = "chat"
+	ResourceChatAutomation                RBACResource = "chat_automation"
 	ResourceConnectionLog                 RBACResource = "connection_log"
 	ResourceCryptoKey                     RBACResource = "crypto_key"
 	ResourceDebugInfo                     RBACResource = "debug_info"
@@ -84,6 +85,7 @@ var RBACResourceActions = map[RBACResource][]RBACAction{
 	ResourceAuditLog:                      {ActionCreate, ActionRead},
 	ResourceBoundaryUsage:                 {ActionDelete, ActionRead, ActionUpdate},
 	ResourceChat:                          {ActionCreate, ActionDelete, ActionRead, ActionUpdate},
+	ResourceChatAutomation:                {ActionCreate, ActionDelete, ActionRead, ActionUpdate},
 	ResourceConnectionLog:                 {ActionRead, ActionUpdate},
 	ResourceCryptoKey:                     {ActionCreate, ActionDelete, ActionRead, ActionUpdate},
 	ResourceDebugInfo:                     {ActionRead},

codersdk/rbacroles.go

@@ -1,12 +1,13 @@
 package codersdk
 
-// Ideally this roles would be generated from the rbac/roles.go package.
+// Ideally these roles would be generated from the rbac/roles.go package.
 const (
 	RoleOwner         string = "owner"
 	RoleMember        string = "member"
 	RoleTemplateAdmin string = "template-admin"
 	RoleUserAdmin     string = "user-admin"
 	RoleAuditor       string = "auditor"
+	RoleAgentsAccess  string = "agents-access"
 
 	RoleOrganizationAdmin                string = "organization-admin"
 	RoleOrganizationMember               string = "organization-member"

codersdk/workspacesdk/tunneler/tunneler.go

@@ -31,17 +31,35 @@ type WorkspaceStarter interface {
 	StartWorkspace() error
 }
 
+type Client interface {
+	DialAgent(dialCtx context.Context, agentID uuid.UUID, options *workspacesdk.DialAgentOptions) (workspacesdk.AgentConn, error)
+}
+
 const (
+	// stateInit is the initial state of the FSM.
 	stateInit state = iota
+	// exit is the final state of the FSM, and implies that everything is closed or closing.
 	exit
+	// waitToStart means the workspace is in a state where we have to wait before we can create a new start build
 	waitToStart
+	// waitForWorkspaceStarted means the workspace is starting, or we have kicked off a goroutine to start it
 	waitForWorkspaceStarted
+	// waitForAgent means the workspace has started and we are waiting for the agent to connect or be ready
 	waitForAgent
+	// establishTailnet means we have kicked off a goroutine to dial the agent and are waiting for its results
 	establishTailnet
+	// tailnetUp means the tailnet connection came up and we kicked off a goroutine to start the NetworkedApplication.
 	tailnetUp
+	// applicationUp means the NetworkedApplication is up.
 	applicationUp
+	// shutdownApplication means we are in graceful shut down and waiting for the NetworkedApplication. It could be
+	// starting or closing, and we expect to get a networkedApplicationUpdate event when it does.
 	shutdownApplication
+	// shutdownTailnet means that we are in graceful shut down and waiting for the tailnet. This implies the
+	// NetworkedApplication is status is down. E.g. closed or was never started.
 	shutdownTailnet
+	// maxState is not a valid state for the FSM, and must be last in this list. It allows tests to iterate over all
+	// valid states using `range maxState`.
 	maxState // used for testing
 )
 
@@ -49,7 +67,7 @@ type Tunneler struct {
 	config    Config
 	ctx       context.Context
 	cancel    context.CancelFunc
-	client    *workspacesdk.Client
+	client    Client
 	state     state
 	agentConn workspacesdk.AgentConn
 	events    chan tunnelerEvent
@@ -98,22 +116,24 @@ type buildUpdate struct {
 }
 
 type agentUpdate struct {
-	// TODO: commented out to appease linter
-	// transition codersdk.WorkspaceTransition
-	// id         uuid.UUID
+	lifecycle codersdk.WorkspaceAgentLifecycle
+	id        uuid.UUID
 }
 
 type networkedApplicationUpdate struct {
 	// up is true if the application is up. False if it is down.
-	up bool
+	up  bool
+	err error
 }
 
 type tailnetUpdate struct {
 	// up is true if the tailnet is up. False if it is down.
-	up bool
+	up   bool
+	conn workspacesdk.AgentConn
+	err  error
 }
 
-func NewTunneler(client *workspacesdk.Client, config Config) *Tunneler {
+func NewTunneler(client Client, config Config) *Tunneler {
 	t := &Tunneler{
 		config: config,
 		client: client,
@@ -166,13 +186,17 @@ func (t *Tunneler) handleSignal() {
 	switch t.state {
 	case exit, shutdownTailnet, shutdownApplication:
 		return
-	case tailnetUp, applicationUp:
+	case applicationUp:
 		t.wg.Add(1)
 		go t.closeApp()
 		t.state = shutdownApplication
+	case tailnetUp:
+		// waiting for app to start; setting state here will cause us to tear it down when the app start goroutine
+		// event comes in.
+		t.state = shutdownApplication
 	case establishTailnet:
-		t.wg.Add(1)
-		go t.shutdownTailnet()
+		// waiting for tailnet to start; setting state here will cause us to tear it down when the tailnet dial
+		// goroutine event comes in.
 		t.state = shutdownTailnet
 	case stateInit, waitToStart, waitForWorkspaceStarted, waitForAgent:
 		t.cancel() // stops the watch
@@ -212,13 +236,12 @@ func (t *Tunneler) handleBuildUpdate(update *buildUpdate) {
 	if update.transition == codersdk.WorkspaceTransitionStart && canMakeProgress {
 		t.config.DebugLogger.Debug(t.ctx, "workspace is starting", slog.F("job_status", update.jobStatus))
 		switch t.state {
-		case establishTailnet:
-			// new build after we're already connecting
-			t.wg.Add(1)
-			go t.shutdownTailnet()
+		// new build after we have already connected
+		case establishTailnet: // we are starting the tailnet
 			t.state = shutdownTailnet
-		case applicationUp, tailnetUp:
-			// new build after we have already connected
+		case tailnetUp: // we are starting the application
+			t.state = shutdownApplication
+		case applicationUp:
 			t.wg.Add(1)
 			go t.closeApp()
 			t.state = shutdownApplication
@@ -241,14 +264,14 @@ func (t *Tunneler) handleBuildUpdate(update *buildUpdate) {
 	if update.transition == codersdk.WorkspaceTransitionStop {
 		// these cases take effect regardless of whether the transition is complete or not
 		switch t.state {
-		case establishTailnet:
-			// new build after we're already connecting
-			t.wg.Add(1)
-			go t.shutdownTailnet()
+		// all 3 of these mean a new build after we have already started connecting
+		case establishTailnet: // waiting for tailnet to start
 			t.state = shutdownTailnet
 			return
-		case applicationUp, tailnetUp:
-			// new build after we have already connected
+		case tailnetUp: // waiting for application to start
+			t.state = shutdownApplication
+			return
+		case applicationUp:
 			t.wg.Add(1)
 			go t.closeApp()
 			t.state = shutdownApplication
@@ -289,7 +312,39 @@ func (t *Tunneler) handleBuildUpdate(update *buildUpdate) {
 func (*Tunneler) handleProvisionerJobLog(*codersdk.ProvisionerJobLog) {
 }
 
-func (*Tunneler) handleAgentUpdate(*agentUpdate) {
+func (t *Tunneler) handleAgentUpdate(update *agentUpdate) {
+	if t.state != waitForAgent {
+		return
+	}
+	doConnect := func() {
+		t.wg.Add(1)
+		t.state = establishTailnet
+		go t.connectTailnet(update.id)
+	}
+	// consequence of ignoring updates if we are not waiting for the agent is that we MUST receive
+	// the start build succeeded update BEFORE we get the Agent connected / ready update.  We should keep this
+	// in mind when implementing the watch in Coderd.
+	switch update.lifecycle {
+	case codersdk.WorkspaceAgentLifecycleReady:
+		doConnect()
+		return
+	case codersdk.WorkspaceAgentLifecycleStarting,
+		codersdk.WorkspaceAgentLifecycleStartError,
+		codersdk.WorkspaceAgentLifecycleStartTimeout:
+		if t.config.NoWaitForScripts {
+			doConnect()
+			return
+		}
+	case codersdk.WorkspaceAgentLifecycleShuttingDown:
+	case codersdk.WorkspaceAgentLifecycleShutdownError:
+	case codersdk.WorkspaceAgentLifecycleShutdownTimeout:
+	case codersdk.WorkspaceAgentLifecycleOff:
+	case codersdk.WorkspaceAgentLifecycleCreated: // initial state, so it hasn't connected yet
+	default:
+		// unhittable, unless new states are added. We structure this with the switch and all cases covered to ensure
+		// we cover all cases.
+		t.config.DebugLogger.Critical(t.ctx, "unhandled agent update", slog.F("lifecycle", update.lifecycle))
+	}
 }
 
 func (*Tunneler) handleAgentLog(*codersdk.WorkspaceAgentLog) {
@@ -310,7 +365,7 @@ func (t *Tunneler) closeApp() {
 	select {
 	case <-t.ctx.Done():
 		t.config.DebugLogger.Info(t.ctx, "context expired before sending app down")
-	case t.events <- tunnelerEvent{appUpdate: &networkedApplicationUpdate{up: false}}:
+	case t.events <- tunnelerEvent{appUpdate: &networkedApplicationUpdate{up: false, err: err}}:
 	}
 }
 
@@ -325,20 +380,44 @@ func (t *Tunneler) startWorkspace() {
 		select {
 		case <-t.ctx.Done():
 			t.config.DebugLogger.Info(t.ctx, "context expired before sending signal after failed workspace start")
-		case t.events <- tunnelerEvent{shutdownSignal: &shutdownSignal{}}:
+		case t.events <- tunnelerEvent{appUpdate: &networkedApplicationUpdate{up: false}}:
 		}
 	}
 }
 
-func (t *Tunneler) shutdownTailnet() {
+func (t *Tunneler) connectTailnet(id uuid.UUID) {
 	defer t.wg.Done()
-	err := t.agentConn.Close()
+	conn, err := t.client.DialAgent(t.ctx, id, &workspacesdk.DialAgentOptions{
+		Logger: t.config.DebugLogger.Named("dialer"),
+	})
 	if err != nil {
-		t.config.DebugLogger.Error(t.ctx, "failed to close agent connection", slog.Error(err))
+		t.config.DebugLogger.Error(t.ctx, "failed to connect agent", slog.Error(err))
+		if t.config.LogWriter != nil {
+			_, _ = fmt.Fprintf(t.config.LogWriter, "failed to dial workspace agent: %s", err.Error())
+		}
+		select {
+		case <-t.ctx.Done():
+			t.config.DebugLogger.Info(t.ctx, "context expired before sending event after failed agent dial")
+		case t.events <- tunnelerEvent{tailnetUpdate: &tailnetUpdate{up: false, err: err}}:
+		}
 	}
 	select {
 	case <-t.ctx.Done():
-		t.config.DebugLogger.Debug(t.ctx, "context expired before sending event after shutting down tailnet")
-	case t.events <- tunnelerEvent{tailnetUpdate: &tailnetUpdate{up: false}}:
+		t.config.DebugLogger.Info(t.ctx, "context expired before sending tailnet conn")
+	case t.events <- tunnelerEvent{tailnetUpdate: &tailnetUpdate{up: true, conn: conn}}:
 	}
 }
+
+// TODO: Restore this func when we implement tearing down the tailnet
+// func (t *Tunneler) shutdownTailnet() {
+//	defer t.wg.Done()
+//	err := t.agentConn.Close()
+//	if err != nil {
+//		t.config.DebugLogger.Error(t.ctx, "failed to close agent connection", slog.Error(err))
+//	}
+//	select {
+//	case <-t.ctx.Done():
+//		t.config.DebugLogger.Debug(t.ctx, "context expired before sending event after shutting down tailnet")
+//	case t.events <- tunnelerEvent{tailnetUpdate: &tailnetUpdate{up: false, err: err}}:
+//	}
+//}

codersdk/workspacesdk/tunneler/tunneler_internal_test.go

@@ -27,46 +27,9 @@ func TestHandleBuildUpdate_Coverage(t *testing.T) {
 					for _, noWaitForScripts := range []bool{true, false} {
 						t.Run(fmt.Sprintf("%d_%s_%s_%t_%t", s, trans, jobStatus, noAutostart, noWaitForScripts), func(t *testing.T) {
 							t.Parallel()
-							ctrl := gomock.NewController(t)
-							mAgentConn := agentconnmock.NewMockAgentConn(ctrl)
-							logger := testutil.Logger(t)
-
-							testCtx := testutil.Context(t, testutil.WaitShort)
-							ctx, cancel := context.WithCancel(testCtx)
-							uut := &Tunneler{
-								config: Config{
-									WorkspaceID:      workspaceID,
-									App:              fakeApp{},
-									WorkspaceStarter: &fakeWorkspaceStarter{},
-									AgentName:        "test",
-									NoAutostart:      noAutostart,
-									NoWaitForScripts: noWaitForScripts,
-									DebugLogger:      logger.Named("tunneler"),
-								},
-								events:    make(chan tunnelerEvent),
-								ctx:       ctx,
-								cancel:    cancel,
-								state:     s,
-								agentConn: mAgentConn,
-							}
-
-							mAgentConn.EXPECT().Close().Return(nil).AnyTimes()
-
-							uut.handleBuildUpdate(&buildUpdate{transition: trans, jobStatus: jobStatus})
-							done := make(chan struct{})
-							go func() {
-								defer close(done)
-								uut.wg.Wait()
-							}()
-							cancel() // cancel in case the update triggers a go routine that writes another event
-							// ensure we don't leak a go routine
-							_ = testutil.TryReceive(testCtx, t, done)
-
-							// We're not asserting the resulting state, as there are just too many to directly enumerate
-							// due to the combinations. Unhandled cases will hit a critical log in the handler and fail
-							// the test.
-							require.Less(t, uut.state, maxState)
-							require.GreaterOrEqual(t, uut.state, 0)
+							coverUpdate(t, workspaceID, noAutostart, noWaitForScripts, s, func(uut *Tunneler) {
+								uut.handleBuildUpdate(&buildUpdate{transition: trans, jobStatus: jobStatus})
+							})
 						})
 					}
 				}
@@ -75,6 +38,51 @@ func TestHandleBuildUpdate_Coverage(t *testing.T) {
 	}
 }
 
+func coverUpdate(t *testing.T, workspaceID uuid.UUID, noAutostart bool, noWaitForScripts bool, s state, update func(uut *Tunneler)) {
+	ctrl := gomock.NewController(t)
+	mAgentConn := agentconnmock.NewMockAgentConn(ctrl)
+	logger := testutil.Logger(t)
+	fClient := &fakeClient{conn: mAgentConn}
+
+	testCtx := testutil.Context(t, testutil.WaitShort)
+	ctx, cancel := context.WithCancel(testCtx)
+	uut := &Tunneler{
+		client: fClient,
+		config: Config{
+			WorkspaceID:      workspaceID,
+			App:              fakeApp{},
+			WorkspaceStarter: &fakeWorkspaceStarter{},
+			AgentName:        "test",
+			NoAutostart:      noAutostart,
+			NoWaitForScripts: noWaitForScripts,
+			DebugLogger:      logger.Named("tunneler"),
+		},
+		events:    make(chan tunnelerEvent),
+		ctx:       ctx,
+		cancel:    cancel,
+		state:     s,
+		agentConn: mAgentConn,
+	}
+
+	mAgentConn.EXPECT().Close().Return(nil).AnyTimes()
+
+	update(uut)
+	done := make(chan struct{})
+	go func() {
+		defer close(done)
+		uut.wg.Wait()
+	}()
+	cancel() // cancel in case the update triggers a go routine that writes another event
+	// ensure we don't leak a go routine
+	_ = testutil.TryReceive(testCtx, t, done)
+
+	// We're not asserting the resulting state, as there are just too many to directly enumerate
+	// due to the combinations. Unhandled cases will hit a critical log in the handler and fail
+	// the test.
+	require.Less(t, uut.state, maxState)
+	require.GreaterOrEqual(t, uut.state, 0)
+}
+
 func TestBuildUpdatesStoppedWorkspace(t *testing.T) {
 	t.Parallel()
 	workspaceID := uuid.UUID{1}
@@ -234,6 +242,96 @@ func TestBuildUpdatesNoAutostart(t *testing.T) {
 	require.Error(t, ctx.Err())
 }
 
+func TestAgentUpdate_Coverage(t *testing.T) {
+	t.Parallel()
+	workspaceID := uuid.UUID{1}
+	agentID := uuid.UUID{2}
+
+	for s := range maxState {
+		for _, lifecycle := range codersdk.WorkspaceAgentLifecycleOrder {
+			for _, noAutostart := range []bool{true, false} {
+				for _, noWaitForScripts := range []bool{true, false} {
+					t.Run(fmt.Sprintf("%d_%s_%t_%t", s, lifecycle, noAutostart, noWaitForScripts), func(t *testing.T) {
+						t.Parallel()
+						coverUpdate(t, workspaceID, noAutostart, noWaitForScripts, s, func(uut *Tunneler) {
+							uut.handleAgentUpdate(&agentUpdate{lifecycle: lifecycle, id: agentID})
+						})
+					})
+				}
+			}
+		}
+	}
+}
+
+func TestAgentUpdateReady(t *testing.T) {
+	t.Parallel()
+	workspaceID := uuid.UUID{1}
+	agentID := uuid.UUID{2}
+	logger := testutil.Logger(t)
+
+	ctrl := gomock.NewController(t)
+	mAgentConn := agentconnmock.NewMockAgentConn(ctrl)
+	fClient := &fakeClient{conn: mAgentConn}
+
+	testCtx := testutil.Context(t, testutil.WaitShort)
+	ctx, cancel := context.WithCancel(testCtx)
+	uut := &Tunneler{
+		config: Config{
+			WorkspaceID: workspaceID,
+			AgentName:   "test",
+			DebugLogger: logger.Named("tunneler"),
+		},
+		events: make(chan tunnelerEvent),
+		ctx:    ctx,
+		cancel: cancel,
+		state:  waitForAgent,
+		client: fClient,
+	}
+
+	uut.handleAgentUpdate(&agentUpdate{lifecycle: codersdk.WorkspaceAgentLifecycleReady, id: agentID})
+	require.Equal(t, establishTailnet, uut.state)
+	event := testutil.RequireReceive(testCtx, t, uut.events)
+	require.NotNil(t, event.tailnetUpdate)
+	require.True(t, fClient.dialed)
+	require.Equal(t, mAgentConn, event.tailnetUpdate.conn)
+	require.True(t, event.tailnetUpdate.up)
+}
+
+func TestAgentUpdateNoWait(t *testing.T) {
+	t.Parallel()
+	workspaceID := uuid.UUID{1}
+	agentID := uuid.UUID{2}
+	logger := testutil.Logger(t)
+
+	ctrl := gomock.NewController(t)
+	mAgentConn := agentconnmock.NewMockAgentConn(ctrl)
+	fClient := &fakeClient{conn: mAgentConn}
+
+	testCtx := testutil.Context(t, testutil.WaitShort)
+	ctx, cancel := context.WithCancel(testCtx)
+	uut := &Tunneler{
+		config: Config{
+			WorkspaceID:      workspaceID,
+			AgentName:        "test",
+			DebugLogger:      logger.Named("tunneler"),
+			NoWaitForScripts: true,
+		},
+		events: make(chan tunnelerEvent),
+		ctx:    ctx,
+		cancel: cancel,
+		state:  waitForAgent,
+		client: fClient,
+	}
+
+	uut.handleAgentUpdate(&agentUpdate{lifecycle: codersdk.WorkspaceAgentLifecycleStarting, id: agentID})
+	require.Equal(t, establishTailnet, uut.state)
+	event := testutil.RequireReceive(testCtx, t, uut.events)
+	require.NotNil(t, event.tailnetUpdate)
+	require.True(t, fClient.dialed)
+	require.Equal(t, mAgentConn, event.tailnetUpdate.conn)
+	require.True(t, event.tailnetUpdate.up)
+}
+
 func waitForGoroutines(ctx context.Context, t *testing.T, tunneler *Tunneler) {
 	done := make(chan struct{})
 	go func() {
@@ -259,3 +357,13 @@ func (fakeApp) Close() error {
 }
 
 func (fakeApp) Start(workspacesdk.AgentConn) {}
+
+type fakeClient struct {
+	conn   workspacesdk.AgentConn
+	dialed bool
+}
+
+func (f *fakeClient) DialAgent(context.Context, uuid.UUID, *workspacesdk.DialAgentOptions) (workspacesdk.AgentConn, error) {
+	f.dialed = true
+	return f.conn, nil
+}

docs/ai-coder/agents/architecture.md

@@ -106,10 +106,15 @@ Tools are how the agent takes action. Each tool call from the LLM translates to
 a concrete operation — either inside a workspace or within the control plane
 itself.
 
-The agent is restricted to the tool set defined in this section. It has no
-direct access to the Coder API beyond what these tools expose and cannot
-execute arbitrary operations against the control plane. If a capability is
-not represented by a tool, the agent cannot perform it.
+The agent is restricted to the built-in tool set defined in this section,
+plus any additional tools from workspace skills and MCP servers. Skills
+provide structured instructions the agent loads on demand
+(see [Extending Agents](./extending-agents.md)). MCP tools come from
+admin-configured external servers
+(see [MCP Servers](./platform-controls/mcp-servers.md)) and from workspace
+`.mcp.json` files. The agent has no direct access to the Coder API beyond
+what these tools expose and cannot execute arbitrary operations against the
+control plane.
 
 ### Workspace connection lifecycle
 
@@ -144,24 +149,26 @@ workspace connection. Platform and orchestration tools are only available to
 root chats — sub-agents spawned by `spawn_agent` do not have access to them
 and cannot create workspaces or spawn further sub-agents.
 
-| Tool               | What it does                                                                           |
-|--------------------|----------------------------------------------------------------------------------------|
-| `list_templates`   | Browses available workspace templates, sorted by popularity.                           |
-| `read_template`    | Gets template details and configurable parameters.                                     |
-| `create_workspace` | Creates a workspace from a template and waits for it to be ready.                      |
-| `start_workspace`  | Starts the chat's workspace if it is currently stopped. Idempotent if already running. |
+| Tool               | What it does                                                                            |
+|--------------------|-----------------------------------------------------------------------------------------|
+| `list_templates`   | Browses available workspace templates, sorted by popularity.                            |
+| `read_template`    | Gets template details and configurable parameters.                                      |
+| `create_workspace` | Creates a workspace from a template and waits for it to be ready.                       |
+| `start_workspace`  | Starts the chat's workspace if it is currently stopped. Idempotent if already running.  |
+| `propose_plan`     | Presents a Markdown plan file from the workspace for user review before implementation. |
 
 ### Orchestration tools
 
 These tools manage sub-agents — child chats that work on independent tasks in
 parallel.
 
-| Tool            | What it does                                                 |
-|-----------------|--------------------------------------------------------------|
-| `spawn_agent`   | Delegates a task to a sub-agent with its own context window. |
-| `wait_agent`    | Waits for a sub-agent to finish and collects its result.     |
-| `message_agent` | Sends a follow-up message to a running sub-agent.            |
-| `close_agent`   | Stops a running sub-agent.                                   |
+| Tool                       | What it does                                                                                                                                                                      |
+|----------------------------|-----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `spawn_agent`              | Delegates a task to a sub-agent with its own context window.                                                                                                                      |
+| `wait_agent`               | Waits for a sub-agent to finish and collects its result.                                                                                                                          |
+| `message_agent`            | Sends a follow-up message to a running sub-agent.                                                                                                                                 |
+| `close_agent`              | Stops a running sub-agent.                                                                                                                                                        |
+| `spawn_computer_use_agent` | Spawns a sub-agent with desktop interaction capabilities (screenshot, mouse, keyboard). Requires an Anthropic provider and the desktop feature to be enabled by an administrator. |
 
 ### Provider tools
 

docs/ai-coder/agents/early-access.md

@@ -65,6 +65,9 @@ Once the server restarts with the experiment enabled:
 1. Navigate to the **Agents** page in the Coder dashboard.
 1. Open **Admin** settings and configure at least one LLM provider and model.
    See [Models](./models.md) for detailed setup instructions.
+1. Grant the **Coder Agents User** role to users who need to create chats.
+   Go to **Admin** > **Users**, click the roles icon next to each user,
+   and enable **Coder Agents User**.
 1. Developers can then start a new chat from the Agents page.
 
 ## Licensing and availability

docs/ai-coder/agents/extending-agents.md

@@ -0,0 +1,130 @@
+# Extending Agents
+
+Workspace templates can extend the agent with custom skills and MCP tools.
+These mechanisms let platform teams provide repository-specific instructions,
+domain expertise, and external tool integrations without modifying the agent
+itself.
+
+## Skills
+
+Skills are structured, reusable instruction sets that the agent loads on
+demand. They live in the workspace filesystem and are discovered
+automatically when a chat attaches to a workspace.
+
+### How skills work
+
+Place skill directories under `.agents/skills/` relative to the workspace
+working directory. Each directory contains a required `SKILL.md` file and
+any supporting files the skill needs.
+
+On the first turn of a workspace-attached chat, the agent scans
+`.agents/skills/` and builds an `<available-skills>` block in its system
+prompt listing each skill's name and description. Only frontmatter is read
+during discovery — the full skill content is loaded lazily when the agent
+calls a tool.
+
+Two tools are registered when skills are present:
+
+| Tool              | Parameters                       | Description                                              |
+|-------------------|----------------------------------|----------------------------------------------------------|
+| `read_skill`      | `name` (string)                  | Returns the SKILL.md body and a list of supporting files |
+| `read_skill_file` | `name` (string), `path` (string) | Returns the content of a supporting file                 |
+
+### Directory structure
+
+```text
+.agents/skills/
+├── deep-review/
+│   ├── SKILL.md
+│   └── roles/
+│       ├── security-reviewer.md
+│       └── concurrency-reviewer.md
+├── pull-requests/
+│   └── SKILL.md
+└── refine-plan/
+    └── SKILL.md
+```
+
+### SKILL.md format
+
+Each `SKILL.md` starts with YAML frontmatter containing a `name` and an
+optional `description`, followed by the full instructions in markdown:
+
+```markdown
+---
+name: deep-review
+description: "Multi-reviewer code review with domain-specific reviewers"
+---
+
+# Deep Review
+
+Instructions for the skill go here...
+```
+
+### Naming and size constraints
+
+- Names must be kebab-case (`^[a-z0-9]+(-[a-z0-9]+)*$`) and match the
+  directory name exactly.
+- `SKILL.md` has a maximum size of 64 KB.
+- Supporting files have a maximum size of 512 KB. Files exceeding the limit
+  are silently truncated.
+
+### Path safety
+
+`read_skill_file` rejects absolute paths, paths containing `..`, and
+references to hidden files. All paths are resolved relative to the skill
+directory.
+
+## Workspace MCP tools
+
+Workspace templates can expose custom
+[MCP](https://modelcontextprotocol.io/introduction) tools by placing a
+`.mcp.json` file in the workspace working directory. The agent discovers
+these tools automatically when it connects to a workspace and registers
+them alongside its built-in tools.
+
+### Configuration
+
+Define MCP servers in `.mcp.json` at the workspace root. Each entry under
+`mcpServers` describes a server. The transport type is inferred from
+whether `command` or `url` is present, or you can set it explicitly with
+`type`:
+
+```json
+{
+  "mcpServers": {
+    "github": {
+      "command": "github-mcp-server",
+      "args": ["--token", "..."]
+    },
+    "my-api": {
+      "type": "http",
+      "url": "http://localhost:8080/mcp",
+      "headers": { "Authorization": "Bearer ..." }
+    }
+  }
+}
+```
+
+**Stdio transport** — set `command`, and optionally `args` and `env`. The
+agent spawns the process in the workspace.
+
+**HTTP transport** — set `url`, and optionally `headers`. The agent connects
+to the HTTP endpoint from the workspace.
+
+### How discovery works
+
+The agent reads `.mcp.json` via the workspace agent connection on each chat
+turn. Discovery uses a 5-second timeout. Servers that fail to
+respond are skipped — partial success is acceptable. Empty results are not
+cached because the MCP servers may still be starting.
+
+### Tool naming
+
+Tool names are prefixed with the server name as `serverName__toolName` to
+avoid collisions between servers and with built-in tools.
+
+### Timeouts
+
+- **Discovery**: 5-second timeout.
+- **Tool calls**: 60 seconds per invocation.

docs/ai-coder/agents/getting-started.md

@@ -24,6 +24,9 @@ Before you begin, confirm the following:
   for the agent to select when provisioning workspaces.
 - **Admin access** to the Coder deployment for enabling the experiment and
   configuring providers.
+- **Coder Agents User role** assigned to each user who needs to create or use chats.
+  Owners can assign this from **Admin** > **Users**. See
+  [Grant Coder Agents User](#step-3-grant-coder-agents-user) below.
 
 ## Step 1: Enable the experiment
 
@@ -69,7 +72,23 @@ Detailed instructions for each provider and model option are in the
 > Start with a single frontier model to validate your setup before adding
 > additional providers.
 
-## Step 3: Start your first chat
+## Step 3: Grant Coder Agents User
+
+The **Coder Agents User** role controls which users can create and use chats.
+Members do not have Coder Agents User by default.
+
+1. Go to **Admin** > **Users** in the Coder dashboard.
+1. Click the roles icon next to the user you want to grant access to.
+1. Enable the **Coder Agents User** role and save.
+
+Repeat for each user who needs access. Owners always have full access
+and do not need the role.
+
+> [!NOTE]
+> Users who created chats before this role was introduced are
+> automatically granted the role during upgrade.
+
+## Step 4: Start your first chat
 
 1. Go to the **Agents** page in the Coder dashboard.
 1. Select a model from the dropdown (your default will be pre-selected).

docs/ai-coder/agents/index.md

@@ -238,10 +238,14 @@ tasks:
 | `read_template`    | Get template details and configurable parameters        |
 | `create_workspace` | Create a workspace from a template                      |
 | `start_workspace`  | Start a stopped workspace for the current chat          |
+| `propose_plan`     | Present a Markdown plan file for user review            |
 | `read_file`        | Read file contents from the workspace                   |
 | `write_file`       | Write a file to the workspace                           |
 | `edit_files`       | Perform search-and-replace edits across files           |
 | `execute`          | Run shell commands in the workspace                     |
+| `process_output`   | Retrieve output from a background process               |
+| `process_list`     | List all tracked processes in the workspace             |
+| `process_signal`   | Send a signal (terminate/kill) to a tracked process     |
 | `spawn_agent`      | Delegate a task to a sub-agent running in parallel      |
 | `wait_agent`       | Wait for a sub-agent to complete and collect its result |
 | `message_agent`    | Send a follow-up message to a running sub-agent         |
@@ -253,7 +257,7 @@ web terminals and IDE access. No additional ports or services are required in
 the workspace.
 
 Platform tools (`list_templates`, `read_template`, `create_workspace`,
-`start_workspace`) and orchestration tools (`spawn_agent`)
+`start_workspace`, `propose_plan`) and orchestration tools (`spawn_agent`)
 are only available to root chats. Sub-agents do
 not have access to these tools and cannot create workspaces or spawn further
 sub-agents.

docs/ai-coder/agents/models.md

@@ -132,11 +132,11 @@ fields appear dynamically in the admin UI when you select a provider.
 
 #### OpenAI
 
-| Option                | Description                                                           |
-|-----------------------|-----------------------------------------------------------------------|
-| Reasoning Effort      | How much effort the model spends reasoning (`low`, `medium`, `high`). |
-| Max Completion Tokens | Cap on completion tokens for reasoning models.                        |
-| Parallel Tool Calls   | Whether the model can call multiple tools at once.                    |
+| Option                | Description                                                                                       |
+|-----------------------|---------------------------------------------------------------------------------------------------|
+| Reasoning Effort      | How much effort the model spends reasoning (`none`, `minimal`, `low`, `medium`, `high`, `xhigh`). |
+| Max Completion Tokens | Cap on completion tokens for reasoning models.                                                    |
+| Parallel Tool Calls   | Whether the model can call multiple tools at once.                                                |
 
 #### Google
 
@@ -144,24 +144,20 @@ fields appear dynamically in the admin UI when you select a provider.
 |------------------|-----------------------------------------------------|
 | Thinking Budget  | Maximum tokens for the model's internal reasoning.  |
 | Include Thoughts | Whether to include thinking traces in the response. |
-| Safety Settings  | Content safety thresholds by category.              |
 
 #### OpenRouter
 
-| Option            | Description                                       |
-|-------------------|---------------------------------------------------|
-| Reasoning Enabled | Enable extended reasoning mode.                   |
-| Reasoning Effort  | Reasoning effort level (`low`, `medium`, `high`). |
-| Provider Order    | Preferred provider routing order.                 |
-| Allow Fallbacks   | Whether to fall back to alternative providers.    |
+| Option            | Description                                                                   |
+|-------------------|-------------------------------------------------------------------------------|
+| Reasoning Enabled | Enable extended reasoning mode.                                               |
+| Reasoning Effort  | Reasoning effort level (`none`, `minimal`, `low`, `medium`, `high`, `xhigh`). |
 
 #### Vercel AI Gateway
 
-| Option            | Description                                   |
-|-------------------|-----------------------------------------------|
-| Reasoning Enabled | Enable extended reasoning mode.               |
-| Reasoning Effort  | Reasoning effort level.                       |
-| Provider Options  | Routing preferences for underlying providers. |
+| Option            | Description                     |
+|-------------------|---------------------------------|
+| Reasoning Enabled | Enable extended reasoning mode. |
+| Reasoning Effort  | Reasoning effort level.         |
 
 > [!NOTE]
 > Azure OpenAI uses the same options as OpenAI. AWS Bedrock uses the same

docs/ai-coder/agents/platform-controls/index.md

@@ -74,24 +74,31 @@ discoverable descriptions, restricting template visibility, configuring network
 boundaries, scoping credentials, and designing template parameters for agent
 use.
 
+### MCP servers
+
+Administrators can register external MCP (Model Context Protocol) servers that
+provide additional tools for agent chat sessions. This includes configuring
+authentication, controlling which tools are exposed via allow/deny lists, and
+setting availability policies that determine whether a server is mandatory,
+opt-out, or opt-in for each chat.
+
+See [MCP Servers](./mcp-servers.md) for configuration details.
+
+### Usage limits and analytics
+
+Administrators can set spend limits to cap LLM usage per user within a rolling
+time period, with per-user and per-group overrides. The cost tracking dashboard
+provides visibility into per-user spending, token consumption, and per-model
+breakdowns.
+
+See [Usage & Analytics](./usage-insights.md) for details.
+
 ## Where we are headed
 
-Coder Agents is in its early stages. The controls above — providers, models,
-and system prompt — are what is available today. We are actively building
-toward a broader set of platform controls based on what we are hearing from
-customers deploying agents in regulated and enterprise environments.
-
-The areas we are investing in include:
-
-### Usage controls and analytics
-
-We plan to give platform teams visibility into how agents are being used across
-the organization: token consumption per user, cost per PR, merge rates by model,
-and average time from prompt to merged pull request.
-
-The goal is to let platform teams make data-driven decisions — like switching
-the default model when analytics show one model produces higher merge rates —
-rather than relying on anecdotal feedback from individual developers.
+The controls above cover providers, models, system prompts, templates, MCP
+servers, and usage limits. We are continuing to invest in platform controls
+based on what we hear from customers deploying agents in regulated and
+enterprise environments.
 
 ### Infrastructure-level enforcement
 
@@ -107,13 +114,6 @@ Examples of what this looks like:
   providers. You can create templates that only permit access to your git
   provider and nothing else.
 
-### Tool customization
-
-The agent ships with a standard set of tools (file read/write, shell execution,
-sub-agents). We intend to let platform teams customize the available tool set —
-adding organization-specific tools or restricting default ones — without
-modifying agent source code.
-
 ## Why we take this approach
 
 The common pattern in the industry today is that each developer installs and

docs/ai-coder/agents/platform-controls/mcp-servers.md

@@ -0,0 +1,125 @@
+# MCP Servers
+
+Administrators can register external MCP servers that provide additional tools
+for agent chat sessions. Configured servers are injected into or offered to
+users during chat depending on the availability policy.
+
+This is an admin-only feature accessible at **Agents** > **Settings** >
+**MCP Servers**.
+
+## Add an MCP server
+
+1. Navigate to **Agents** > **Settings** > **MCP Servers**.
+1. Click **Add**.
+1. Fill in the configuration fields described below.
+1. Click **Save**.
+
+### Identity
+
+| Field          | Required | Description                                                   |
+|----------------|----------|---------------------------------------------------------------|
+| `display_name` | Yes      | Human-readable name shown to users in chat.                   |
+| `slug`         | Yes      | URL-safe unique identifier, auto-generated from display name. |
+| `description`  | No       | Brief summary of what the server provides.                    |
+| `icon_url`     | No       | Emoji or image URL displayed alongside the server name.       |
+
+### Connection
+
+| Field       | Required | Description                                     |
+|-------------|----------|-------------------------------------------------|
+| `url`       | Yes      | The MCP server endpoint URL.                    |
+| `transport` | Yes      | Transport protocol. `streamable_http` or `sse`. |
+
+### Availability
+
+| Field          | Required | Description                                                                                                                   |
+|----------------|----------|-------------------------------------------------------------------------------------------------------------------------------|
+| `enabled`      | No       | Master toggle. Disabled servers are hidden from non-admin users.                                                              |
+| `availability` | Yes      | Controls how the server appears in chat sessions. See [Availability policies](#availability-policies).                        |
+| `model_intent` | No       | When enabled, requires the model to describe each tool call's purpose in natural language, shown as a status label in the UI. |
+
+#### Availability policies
+
+| Policy        | Behavior                                               |
+|---------------|--------------------------------------------------------|
+| `force_on`    | Always injected into every chat. Users cannot opt out. |
+| `default_on`  | Pre-selected in new chats. Users can opt out.          |
+| `default_off` | Available in the server list but users must opt in.    |
+
+## Authentication
+
+Each MCP server uses one of four authentication modes. When you change the
+auth type, fields from the previous type are automatically cleared.
+
+Secrets are never returned in API responses — boolean flags indicate whether
+a value is set.
+
+### None
+
+No credentials are sent. Use this for servers that do not require
+authentication.
+
+### OAuth2
+
+Per-user authorization. The administrator configures the OAuth2 provider, and
+each user independently completes the authorization flow.
+
+**Manual configuration** — provide all three fields together:
+
+| Field              | Description                 |
+|--------------------|-----------------------------|
+| `oauth2_client_id` | OAuth2 client ID.           |
+| `oauth2_auth_url`  | Authorization endpoint URL. |
+| `oauth2_token_url` | Token endpoint URL.         |
+
+Optional fields:
+
+| Field                  | Description                     |
+|------------------------|---------------------------------|
+| `oauth2_client_secret` | OAuth2 client secret.           |
+| `oauth2_scopes`        | Space-separated list of scopes. |
+
+**Auto-discovery** — leave `oauth2_client_id`, `oauth2_auth_url`, and
+`oauth2_token_url` empty. The server attempts discovery in this order:
+
+1. RFC 9728 — Protected Resource Metadata
+1. RFC 8414 — Authorization Server Metadata
+1. RFC 7591 — Dynamic Client Registration
+
+Users connect through a popup that redirects through the OAuth2 provider.
+Tokens are stored per-user and refreshed automatically. Users can disconnect
+via the UI or API to remove stored tokens.
+
+### API key
+
+A static key sent as a header on every request.
+
+| Field            | Required | Description                          |
+|------------------|----------|--------------------------------------|
+| `api_key_header` | Yes      | Header name (e.g., `Authorization`). |
+| `api_key_value`  | Yes      | Secret value sent in the header.     |
+
+### Custom headers
+
+Arbitrary key-value header pairs sent on every request. At least one header
+is required when this mode is selected.
+
+## Tool governance
+
+Control which tools from a server are available in chat:
+
+| Field             | Description                                                                           |
+|-------------------|---------------------------------------------------------------------------------------|
+| `tool_allow_list` | If non-empty, only the listed tool names are exposed. An empty list allows all tools. |
+| `tool_deny_list`  | Listed tool names are always blocked, even if they appear in the allow list.          |
+
+## Permissions
+
+| Action                        | Required role             |
+|-------------------------------|---------------------------|
+| Create, update, or delete     | Admin (deployment config) |
+| View enabled servers          | Any authenticated user    |
+| OAuth2 connect and disconnect | Any authenticated user    |
+
+Non-admin users only see enabled servers. Sensitive fields such as API keys
+and client secrets are redacted in API responses.

docs/ai-coder/agents/platform-controls/usage-insights.md

@@ -0,0 +1,85 @@
+# Usage and Analytics
+
+Coder provides two admin-only views for monitoring and controlling agent
+spend: usage limits and cost tracking.
+
+## Usage limits
+
+Navigate to **Agents** > **Settings** > **Limits**.
+
+Usage limits cap how much each user can spend on LLM usage within a rolling
+time period. When enabled, the system checks the user's current spend before
+processing each chat message.
+
+### Configuration
+
+- **Enable/disable toggle** — master on/off for the entire limit system.
+- **Period** — `day`, `week`, or `month`. Periods are UTC-aligned: midnight
+  UTC for daily, Monday start for weekly, first of the month for monthly.
+- **Default limit** — deployment-wide default in dollars. Applies to all
+  users who do not have a more specific override. Leave unset for no limit.
+- **Per-user overrides** — set a custom dollar limit for an individual user.
+  Takes highest priority.
+- **Per-group overrides** — set a limit for a group. When a user belongs to
+  multiple groups, the lowest group limit applies.
+
+### Priority hierarchy
+
+The system resolves a user's effective limit in this order:
+
+1. Individual user override (highest priority)
+1. Minimum group limit across all of the user's groups
+1. Global default limit
+1. No limit (if limits are disabled or no value is configured)
+
+### Enforcement
+
+- Checked before each chat message is processed.
+- When current spend meets or exceeds the limit, the chat returns a
+  **409 Conflict** response and the message is blocked.
+- Fail-open: if the limit query itself fails, the message is allowed
+  through.
+- Brief overage is possible when concurrent messages are in flight, because
+  cost is determined only after the LLM returns.
+
+### User-facing status
+
+Users can view their own spend status, including whether a limit is active,
+their effective limit, current spend, and when the current period resets.
+
+> [!NOTE]
+> The admin configuration page shows the count of models without pricing
+> data. Models missing pricing cannot be tracked accurately against limits.
+
+## Cost tracking
+
+Navigate to **Agents** > **Settings** > **Usage**.
+
+This view shows deployment-wide LLM chat costs with per-user drill-down.
+
+### Top-level view
+
+A per-user rollup table with the following columns:
+
+| Column             | Description                         |
+|--------------------|-------------------------------------|
+| Total cost         | Aggregate dollar spend for the user |
+| Messages           | Number of chat messages sent        |
+| Chats              | Number of distinct chat sessions    |
+| Input tokens       | Total input tokens consumed         |
+| Output tokens      | Total output tokens consumed        |
+| Cache read tokens  | Tokens served from cache            |
+| Cache write tokens | Tokens written to cache             |
+
+The table supports date range filtering (default: last 30 days), search by
+name or username, and pagination.
+
+### Per-user detail view
+
+Select a user to see:
+
+- **Summary cards** — total cost, token breakdowns, and message counts.
+- **Usage limit progress** — if a limit is active, a color-coded progress
+  bar shows current spend relative to the limit.
+- **Per-model breakdown** — table of costs and token usage by model.
+- **Per-chat breakdown** — table of costs and token usage by chat session.

docs/manifest.json

@@ -324,8 +324,7 @@
 					"title": "Workspace Sharing",
 					"description": "Sharing workspaces",
 					"path": "./user-guides/shared-workspaces.md",
-					"icon_path": "./images/icons/generic.svg",
-					"state": ["beta"]
+					"icon_path": "./images/icons/generic.svg"
 				},
 				{
 					"title": "Workspace Scheduling",
@@ -1238,9 +1237,27 @@
 									"description": "Best practices for creating templates that are discoverable and useful to Coder Agents",
 									"path": "./ai-coder/agents/platform-controls/template-optimization.md",
 									"state": ["early access"]
+								},
+								{
+									"title": "MCP Servers",
+									"description": "Configure external MCP servers that provide additional tools for agent chat sessions",
+									"path": "./ai-coder/agents/platform-controls/mcp-servers.md",
+									"state": ["early access"]
+								},
+								{
+									"title": "Usage \u0026 Analytics",
+									"description": "Spend limits and cost tracking for Coder Agents",
+									"path": "./ai-coder/agents/platform-controls/usage-insights.md",
+									"state": ["early access"]
 								}
 							]
 						},
+						{
+							"title": "Extending Agents",
+							"description": "Add custom skills and MCP tools to agent workspaces",
+							"path": "./ai-coder/agents/extending-agents.md",
+							"state": ["early access"]
+						},
 						{
 							"title": "Chats API",
 							"description": "Programmatic access to Coder Agents via the experimental Chats API",

docs/reference/api/members.md

@@ -193,10 +193,10 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-----------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        |
-| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|-----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).
 
@@ -326,10 +326,10 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-----------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        |
-| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|-----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).
 
@@ -459,10 +459,10 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-----------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        |
-| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|-----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).
 
@@ -554,10 +554,10 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-----------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        |
-| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|-----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).
 
@@ -960,9 +960,9 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-----------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                        |
-| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Property        | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|-----------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `action`        | `application_connect`, `assign`, `create`, `create_agent`, `delete`, `delete_agent`, `read`, `read_personal`, `share`, `ssh`, `start`, `stop`, `unassign`, `update`, `update_agent`, `update_personal`, `use`, `view_insights`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
+| `resource_type` | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).

docs/reference/api/schemas.md

@@ -1286,9 +1286,9 @@
 
 #### Enumerated Values
 
-| Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                           |
-|----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `aibridge_interception:*`, `aibridge_interception:create`, `aibridge_interception:read`, `aibridge_interception:update`, `all`, `api_key:*`, `api_key:create`, `api_key:delete`, `api_key:read`, `api_key:update`, `application_connect`, `assign_org_role:*`, `assign_org_role:assign`, `assign_org_role:create`, `assign_org_role:delete`, `assign_org_role:read`, `assign_org_role:unassign`, `assign_org_role:update`, `assign_role:*`, `assign_role:assign`, `assign_role:read`, `assign_role:unassign`, `audit_log:*`, `audit_log:create`, `audit_log:read`, `boundary_usage:*`, `boundary_usage:delete`, `boundary_usage:read`, `boundary_usage:update`, `chat:*`, `chat:create`, `chat:delete`, `chat:read`, `chat:update`, `coder:all`, `coder:apikeys.manage_self`, `coder:application_connect`, `coder:templates.author`, `coder:templates.build`, `coder:workspaces.access`, `coder:workspaces.create`, `coder:workspaces.delete`, `coder:workspaces.operate`, `connection_log:*`, `connection_log:read`, `connection_log:update`, `crypto_key:*`, `crypto_key:create`, `crypto_key:delete`, `crypto_key:read`, `crypto_key:update`, `debug_info:*`, `debug_info:read`, `deployment_config:*`, `deployment_config:read`, `deployment_config:update`, `deployment_stats:*`, `deployment_stats:read`, `file:*`, `file:create`, `file:read`, `group:*`, `group:create`, `group:delete`, `group:read`, `group:update`, `group_member:*`, `group_member:read`, `idpsync_settings:*`, `idpsync_settings:read`, `idpsync_settings:update`, `inbox_notification:*`, `inbox_notification:create`, `inbox_notification:read`, `inbox_notification:update`, `license:*`, `license:create`, `license:delete`, `license:read`, `notification_message:*`, `notification_message:create`, `notification_message:delete`, `notification_message:read`, `notification_message:update`, `notification_preference:*`, `notification_preference:read`, `notification_preference:update`, `notification_template:*`, `notification_template:read`, `notification_template:update`, `oauth2_app:*`, `oauth2_app:create`, `oauth2_app:delete`, `oauth2_app:read`, `oauth2_app:update`, `oauth2_app_code_token:*`, `oauth2_app_code_token:create`, `oauth2_app_code_token:delete`, `oauth2_app_code_token:read`, `oauth2_app_secret:*`, `oauth2_app_secret:create`, `oauth2_app_secret:delete`, `oauth2_app_secret:read`, `oauth2_app_secret:update`, `organization:*`, `organization:create`, `organization:delete`, `organization:read`, `organization:update`, `organization_member:*`, `organization_member:create`, `organization_member:delete`, `organization_member:read`, `organization_member:update`, `prebuilt_workspace:*`, `prebuilt_workspace:delete`, `prebuilt_workspace:update`, `provisioner_daemon:*`, `provisioner_daemon:create`, `provisioner_daemon:delete`, `provisioner_daemon:read`, `provisioner_daemon:update`, `provisioner_jobs:*`, `provisioner_jobs:create`, `provisioner_jobs:read`, `provisioner_jobs:update`, `replicas:*`, `replicas:read`, `system:*`, `system:create`, `system:delete`, `system:read`, `system:update`, `tailnet_coordinator:*`, `tailnet_coordinator:create`, `tailnet_coordinator:delete`, `tailnet_coordinator:read`, `tailnet_coordinator:update`, `task:*`, `task:create`, `task:delete`, `task:read`, `task:update`, `template:*`, `template:create`, `template:delete`, `template:read`, `template:update`, `template:use`, `template:view_insights`, `usage_event:*`, `usage_event:create`, `usage_event:read`, `usage_event:update`, `user:*`, `user:create`, `user:delete`, `user:read`, `user:read_personal`, `user:update`, `user:update_personal`, `user_secret:*`, `user_secret:create`, `user_secret:delete`, `user_secret:read`, `user_secret:update`, `webpush_subscription:*`, `webpush_subscription:create`, `webpush_subscription:delete`, `webpush_subscription:read`, `workspace:*`, `workspace:application_connect`, `workspace:create`, `workspace:create_agent`, `workspace:delete`, `workspace:delete_agent`, `workspace:read`, `workspace:share`, `workspace:ssh`, `workspace:start`, `workspace:stop`, `workspace:update`, `workspace:update_agent`, `workspace_agent_devcontainers:*`, `workspace_agent_devcontainers:create`, `workspace_agent_resource_monitor:*`, `workspace_agent_resource_monitor:create`, `workspace_agent_resource_monitor:read`, `workspace_agent_resource_monitor:update`, `workspace_dormant:*`, `workspace_dormant:application_connect`, `workspace_dormant:create`, `workspace_dormant:create_agent`, `workspace_dormant:delete`, `workspace_dormant:delete_agent`, `workspace_dormant:read`, `workspace_dormant:share`, `workspace_dormant:ssh`, `workspace_dormant:start`, `workspace_dormant:stop`, `workspace_dormant:update`, `workspace_dormant:update_agent`, `workspace_proxy:*`, `workspace_proxy:create`, `workspace_proxy:delete`, `workspace_proxy:read`, `workspace_proxy:update` |
+| Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                      |
+|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `aibridge_interception:*`, `aibridge_interception:create`, `aibridge_interception:read`, `aibridge_interception:update`, `all`, `api_key:*`, `api_key:create`, `api_key:delete`, `api_key:read`, `api_key:update`, `application_connect`, `assign_org_role:*`, `assign_org_role:assign`, `assign_org_role:create`, `assign_org_role:delete`, `assign_org_role:read`, `assign_org_role:unassign`, `assign_org_role:update`, `assign_role:*`, `assign_role:assign`, `assign_role:read`, `assign_role:unassign`, `audit_log:*`, `audit_log:create`, `audit_log:read`, `boundary_usage:*`, `boundary_usage:delete`, `boundary_usage:read`, `boundary_usage:update`, `chat:*`, `chat:create`, `chat:delete`, `chat:read`, `chat:update`, `chat_automation:*`, `chat_automation:create`, `chat_automation:delete`, `chat_automation:read`, `chat_automation:update`, `coder:all`, `coder:apikeys.manage_self`, `coder:application_connect`, `coder:templates.author`, `coder:templates.build`, `coder:workspaces.access`, `coder:workspaces.create`, `coder:workspaces.delete`, `coder:workspaces.operate`, `connection_log:*`, `connection_log:read`, `connection_log:update`, `crypto_key:*`, `crypto_key:create`, `crypto_key:delete`, `crypto_key:read`, `crypto_key:update`, `debug_info:*`, `debug_info:read`, `deployment_config:*`, `deployment_config:read`, `deployment_config:update`, `deployment_stats:*`, `deployment_stats:read`, `file:*`, `file:create`, `file:read`, `group:*`, `group:create`, `group:delete`, `group:read`, `group:update`, `group_member:*`, `group_member:read`, `idpsync_settings:*`, `idpsync_settings:read`, `idpsync_settings:update`, `inbox_notification:*`, `inbox_notification:create`, `inbox_notification:read`, `inbox_notification:update`, `license:*`, `license:create`, `license:delete`, `license:read`, `notification_message:*`, `notification_message:create`, `notification_message:delete`, `notification_message:read`, `notification_message:update`, `notification_preference:*`, `notification_preference:read`, `notification_preference:update`, `notification_template:*`, `notification_template:read`, `notification_template:update`, `oauth2_app:*`, `oauth2_app:create`, `oauth2_app:delete`, `oauth2_app:read`, `oauth2_app:update`, `oauth2_app_code_token:*`, `oauth2_app_code_token:create`, `oauth2_app_code_token:delete`, `oauth2_app_code_token:read`, `oauth2_app_secret:*`, `oauth2_app_secret:create`, `oauth2_app_secret:delete`, `oauth2_app_secret:read`, `oauth2_app_secret:update`, `organization:*`, `organization:create`, `organization:delete`, `organization:read`, `organization:update`, `organization_member:*`, `organization_member:create`, `organization_member:delete`, `organization_member:read`, `organization_member:update`, `prebuilt_workspace:*`, `prebuilt_workspace:delete`, `prebuilt_workspace:update`, `provisioner_daemon:*`, `provisioner_daemon:create`, `provisioner_daemon:delete`, `provisioner_daemon:read`, `provisioner_daemon:update`, `provisioner_jobs:*`, `provisioner_jobs:create`, `provisioner_jobs:read`, `provisioner_jobs:update`, `replicas:*`, `replicas:read`, `system:*`, `system:create`, `system:delete`, `system:read`, `system:update`, `tailnet_coordinator:*`, `tailnet_coordinator:create`, `tailnet_coordinator:delete`, `tailnet_coordinator:read`, `tailnet_coordinator:update`, `task:*`, `task:create`, `task:delete`, `task:read`, `task:update`, `template:*`, `template:create`, `template:delete`, `template:read`, `template:update`, `template:use`, `template:view_insights`, `usage_event:*`, `usage_event:create`, `usage_event:read`, `usage_event:update`, `user:*`, `user:create`, `user:delete`, `user:read`, `user:read_personal`, `user:update`, `user:update_personal`, `user_secret:*`, `user_secret:create`, `user_secret:delete`, `user_secret:read`, `user_secret:update`, `webpush_subscription:*`, `webpush_subscription:create`, `webpush_subscription:delete`, `webpush_subscription:read`, `workspace:*`, `workspace:application_connect`, `workspace:create`, `workspace:create_agent`, `workspace:delete`, `workspace:delete_agent`, `workspace:read`, `workspace:share`, `workspace:ssh`, `workspace:start`, `workspace:stop`, `workspace:update`, `workspace:update_agent`, `workspace_agent_devcontainers:*`, `workspace_agent_devcontainers:create`, `workspace_agent_resource_monitor:*`, `workspace_agent_resource_monitor:create`, `workspace_agent_resource_monitor:read`, `workspace_agent_resource_monitor:update`, `workspace_dormant:*`, `workspace_dormant:application_connect`, `workspace_dormant:create`, `workspace_dormant:create_agent`, `workspace_dormant:delete`, `workspace_dormant:delete_agent`, `workspace_dormant:read`, `workspace_dormant:share`, `workspace_dormant:ssh`, `workspace_dormant:start`, `workspace_dormant:stop`, `workspace_dormant:update`, `workspace_dormant:update_agent`, `workspace_proxy:*`, `workspace_proxy:create`, `workspace_proxy:delete`, `workspace_proxy:read`, `workspace_proxy:update` |
 
 ## codersdk.AddLicenseRequest
 
@@ -8080,9 +8080,9 @@ Only certain features set these fields: - FeatureManagedAgentLimit|
 
 #### Enumerated Values
 
-| Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
 
 ## codersdk.RateLimitConfig
 

docs/reference/api/users.md

@@ -849,11 +849,11 @@ Status Code **200**
 
 #### Enumerated Values
 
-| Property     | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                              |
-|--------------|-------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
-| `type`       | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
-| `login_type` | `github`, `oidc`, `password`, `token`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
-| `scope`      | `all`, `application_connect`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                          |
+| Property     | Value(s)                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                 |
+|--------------|--------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------|
+| `type`       | `*`, `aibridge_interception`, `api_key`, `assign_org_role`, `assign_role`, `audit_log`, `boundary_usage`, `chat`, `chat_automation`, `connection_log`, `crypto_key`, `debug_info`, `deployment_config`, `deployment_stats`, `file`, `group`, `group_member`, `idpsync_settings`, `inbox_notification`, `license`, `notification_message`, `notification_preference`, `notification_template`, `oauth2_app`, `oauth2_app_code_token`, `oauth2_app_secret`, `organization`, `organization_member`, `prebuilt_workspace`, `provisioner_daemon`, `provisioner_jobs`, `replicas`, `system`, `tailnet_coordinator`, `task`, `template`, `usage_event`, `user`, `user_secret`, `webpush_subscription`, `workspace`, `workspace_agent_devcontainers`, `workspace_agent_resource_monitor`, `workspace_dormant`, `workspace_proxy` |
+| `login_type` | `github`, `oidc`, `password`, `token`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                    |
+| `scope`      | `all`, `application_connect`                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                             |
 
 To perform this operation, you must be authenticated. [Learn more](authentication.md).
 

dogfood/coder/Dockerfile

@@ -11,8 +11,8 @@ RUN cargo install jj-cli typos-cli watchexec-cli
 FROM ubuntu:jammy@sha256:ce4a593b4e323dcc3dd728e397e0a866a1bf516a1b7c31d6aa06991baec4f2e0 AS go
 
 # Install Go manually, so that we can control the version
-ARG GO_VERSION=1.25.7
-ARG GO_CHECKSUM="12e6d6a191091ae27dc31f6efc630e3a3b8ba409baf3573d955b196fdf086005"
+ARG GO_VERSION=1.25.8
+ARG GO_CHECKSUM="ceb5e041bbc3893846bd1614d76cb4681c91dadee579426cf21a63f2d7e03be6"
 
 # Boring Go is needed to build FIPS-compliant binaries.
 RUN apt-get update && \

enterprise/aibridgeproxyd/aibridgeproxyd.go

@@ -776,6 +776,12 @@ func defaultAIBridgeProvider(host string) string {
 		return aibridge.ProviderOpenAI
 	case HostCopilot:
 		return aibridge.ProviderCopilot
+	case agplaibridge.HostCopilotBusiness:
+		return agplaibridge.ProviderCopilotBusiness
+	case agplaibridge.HostCopilotEnterprise:
+		return agplaibridge.ProviderCopilotEnterprise
+	case agplaibridge.HostChatGPT:
+		return agplaibridge.ProviderChatGPT
 	default:
 		return ""
 	}

enterprise/cli/aibridged.go

@@ -10,6 +10,7 @@ import (
 
 	"github.com/coder/aibridge"
 	"github.com/coder/aibridge/config"
+	agplaibridge "github.com/coder/coder/v2/coderd/aibridge"
 	"github.com/coder/coder/v2/coderd/tracing"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/enterprise/aibridged"
@@ -37,20 +38,39 @@ func newAIBridgeDaemon(coderAPI *coderd.API) (*aibridged.Server, error) {
 	// Setup supported providers with circuit breaker config.
 	providers := []aibridge.Provider{
 		aibridge.NewOpenAIProvider(aibridge.OpenAIConfig{
+			Name:             aibridge.ProviderOpenAI,
 			BaseURL:          cfg.OpenAI.BaseURL.String(),
 			Key:              cfg.OpenAI.Key.String(),
 			CircuitBreaker:   cbConfig,
 			SendActorHeaders: cfg.SendActorHeaders.Value(),
 		}),
 		aibridge.NewAnthropicProvider(aibridge.AnthropicConfig{
+			Name:             aibridge.ProviderAnthropic,
 			BaseURL:          cfg.Anthropic.BaseURL.String(),
 			Key:              cfg.Anthropic.Key.String(),
 			CircuitBreaker:   cbConfig,
 			SendActorHeaders: cfg.SendActorHeaders.Value(),
 		}, getBedrockConfig(cfg.Bedrock)),
 		aibridge.NewCopilotProvider(aibridge.CopilotConfig{
+			Name:           aibridge.ProviderCopilot,
 			CircuitBreaker: cbConfig,
 		}),
+		aibridge.NewCopilotProvider(aibridge.CopilotConfig{
+			Name:           agplaibridge.ProviderCopilotBusiness,
+			BaseURL:        "https://" + agplaibridge.HostCopilotBusiness,
+			CircuitBreaker: cbConfig,
+		}),
+		aibridge.NewCopilotProvider(aibridge.CopilotConfig{
+			Name:           agplaibridge.ProviderCopilotEnterprise,
+			BaseURL:        "https://" + agplaibridge.HostCopilotEnterprise,
+			CircuitBreaker: cbConfig,
+		}),
+		aibridge.NewOpenAIProvider(aibridge.OpenAIConfig{
+			Name:             agplaibridge.ProviderChatGPT,
+			BaseURL:          agplaibridge.BaseURLChatGPT,
+			CircuitBreaker:   cbConfig,
+			SendActorHeaders: cfg.SendActorHeaders.Value(),
+		}),
 	}
 
 	reg := prometheus.WrapRegistererWithPrefix("coder_aibridged_", coderAPI.PrometheusRegistry)

enterprise/coderd/aibridge_test.go

@@ -440,7 +440,7 @@ func TestAIBridgeListInterceptions(t *testing.T) {
 			},
 			{
 				name:   "Client/Unknown",
-				filter: codersdk.AIBridgeListInterceptionsFilter{Client: "Unknown"},
+				filter: codersdk.AIBridgeListInterceptionsFilter{Client: string(aiblib.ClientUnknown)},
 				want:   []codersdk.AIBridgeInterception{i1SDK},
 			},
 			{
@@ -1213,6 +1213,302 @@ func TestAIBridgeListSessions(t *testing.T) {
 		require.Contains(t, sdkErr.Message, "Invalid pagination limit value.")
 		require.Empty(t, res.Sessions)
 	})
+
+	t.Run("StartedBeforeFilter", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// Session started recently.
+		recentEndedAt := now.Add(time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			StartedAt:   now,
+		}, &recentEndedAt)
+
+		// Session started 2 hours ago.
+		oldEndedAt := now.Add(-2*time.Hour + time.Minute)
+		old := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			StartedAt:   now.Add(-2 * time.Hour),
+		}, &oldEndedAt)
+
+		// Only the old session should be returned when started_before
+		// is set to 1 hour ago.
+		//nolint:gocritic // Owner role is irrelevant; testing filter.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{
+			StartedBefore: now.Add(-time.Hour),
+		})
+		require.NoError(t, err)
+		require.EqualValues(t, 1, res.Count)
+		require.Len(t, res.Sessions, 1)
+		require.Equal(t, old.ID.String(), res.Sessions[0].ID)
+	})
+
+	t.Run("NullClientCoalescesToUnknown", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// Session with explicit client.
+		withClientEndedAt := now.Add(time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			StartedAt:   now,
+			Client:      sql.NullString{String: "claude-code", Valid: true},
+		}, &withClientEndedAt)
+
+		// Session with NULL client (should COALESCE to ClientUnknown).
+		nullClientEndedAt := now.Add(-time.Hour + time.Minute)
+		nullClient := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			StartedAt:   now.Add(-time.Hour),
+			// Client field deliberately omitted (NULL).
+		}, &nullClientEndedAt)
+
+		// Filtering by ClientUnknown should return only the NULL-client
+		// session.
+		//nolint:gocritic // Owner role is irrelevant; testing COALESCE.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{
+			Client: string(aiblib.ClientUnknown),
+		})
+		require.NoError(t, err)
+		require.EqualValues(t, 1, res.Count)
+		require.Len(t, res.Sessions, 1)
+		require.Equal(t, nullClient.ID.String(), res.Sessions[0].ID)
+	})
+
+	t.Run("MetadataFromFirstInterception", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// First interception (chronologically) carries the expected
+		// metadata for the session.
+		i1EndedAt := now.Add(time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       now,
+			Metadata:        json.RawMessage(`{"editor":"vscode"}`),
+			Client:          sql.NullString{String: "claude-code", Valid: true},
+			ClientSessionID: sql.NullString{String: "meta-session", Valid: true},
+		}, &i1EndedAt)
+
+		// Second interception has different metadata.
+		i2EndedAt := now.Add(2 * time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       now.Add(time.Minute),
+			Metadata:        json.RawMessage(`{"editor":"jetbrains"}`),
+			Client:          sql.NullString{String: "claude-code", Valid: true},
+			ClientSessionID: sql.NullString{String: "meta-session", Valid: true},
+		}, &i2EndedAt)
+
+		//nolint:gocritic // Owner role is irrelevant; testing metadata.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{})
+		require.NoError(t, err)
+		require.Len(t, res.Sessions, 1)
+		// Metadata should come from the first interception.
+		require.Equal(t, "vscode", res.Sessions[0].Metadata["editor"])
+	})
+
+	t.Run("SessionTimestamps", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// Two interceptions in the same session with different
+		// started_at and ended_at values. The session should report
+		// MIN(started_at) and MAX(ended_at).
+		i1StartedAt := now
+		i1EndedAt := now.Add(time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       i1StartedAt,
+			ClientSessionID: sql.NullString{String: "ts-session", Valid: true},
+		}, &i1EndedAt)
+
+		i2StartedAt := now.Add(2 * time.Minute)
+		i2EndedAt := now.Add(5 * time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       i2StartedAt,
+			ClientSessionID: sql.NullString{String: "ts-session", Valid: true},
+		}, &i2EndedAt)
+
+		//nolint:gocritic // Owner role is irrelevant; testing timestamps.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{})
+		require.NoError(t, err)
+		require.Len(t, res.Sessions, 1)
+		s := res.Sessions[0]
+		require.WithinDuration(t, i1StartedAt, s.StartedAt, time.Millisecond,
+			"session started_at should be MIN of interception started_at values")
+		require.NotNil(t, s.EndedAt)
+		require.WithinDuration(t, i2EndedAt, *s.EndedAt, time.Millisecond,
+			"session ended_at should be MAX of interception ended_at values")
+	})
+
+	t.Run("LastPromptAcrossInterceptions", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// Two interceptions in the same session.
+		i1EndedAt := now.Add(time.Minute)
+		i1 := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       now,
+			ClientSessionID: sql.NullString{String: "prompt-session", Valid: true},
+		}, &i1EndedAt)
+		i2EndedAt := now.Add(3 * time.Minute)
+		i2 := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID:     firstUser.UserID,
+			StartedAt:       now.Add(2 * time.Minute),
+			ClientSessionID: sql.NullString{String: "prompt-session", Valid: true},
+		}, &i2EndedAt)
+
+		// Add prompts to both interceptions. The most recent prompt
+		// overall belongs to the second interception.
+		dbgen.AIBridgeUserPrompt(t, db, database.InsertAIBridgeUserPromptParams{
+			InterceptionID: i1.ID,
+			Prompt:         "early prompt from i1",
+			CreatedAt:      now,
+		})
+		dbgen.AIBridgeUserPrompt(t, db, database.InsertAIBridgeUserPromptParams{
+			InterceptionID: i2.ID,
+			Prompt:         "latest prompt from i2",
+			CreatedAt:      now.Add(2 * time.Minute),
+		})
+
+		//nolint:gocritic // Owner role is irrelevant; testing lateral join.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{})
+		require.NoError(t, err)
+		require.Len(t, res.Sessions, 1)
+		require.NotNil(t, res.Sessions[0].LastPrompt)
+		require.Equal(t, "latest prompt from i2", *res.Sessions[0].LastPrompt,
+			"last_prompt should be the most recent prompt across all interceptions in the session")
+	})
+
+	t.Run("CombinedFilters", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		_, user2 := coderdtest.CreateAnotherUser(t, client, firstUser.OrganizationID)
+
+		now := dbtime.Now()
+
+		// Session A: user1, anthropic, claude-4, started now.
+		aEndedAt := now.Add(time.Minute)
+		a := dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			Provider:    "anthropic",
+			Model:       "claude-4",
+			StartedAt:   now,
+		}, &aEndedAt)
+
+		// Session B: user1, anthropic, gpt-4, started 2h ago.
+		bEndedAt := now.Add(-2*time.Hour + time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: firstUser.UserID,
+			Provider:    "anthropic",
+			Model:       "gpt-4",
+			StartedAt:   now.Add(-2 * time.Hour),
+		}, &bEndedAt)
+
+		// Session C: user2, anthropic, claude-4, started 1h ago.
+		cEndedAt := now.Add(-time.Hour + time.Minute)
+		dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+			InitiatorID: user2.ID,
+			Provider:    "anthropic",
+			Model:       "claude-4",
+			StartedAt:   now.Add(-time.Hour),
+		}, &cEndedAt)
+
+		// Combining provider + model + started_after should return
+		// only session A (user1, anthropic, claude-4, recent).
+		//nolint:gocritic // Owner role is irrelevant; testing combined filters.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{
+			Provider:     "anthropic",
+			Model:        "claude-4",
+			StartedAfter: now.Add(-30 * time.Minute),
+		})
+		require.NoError(t, err)
+		require.EqualValues(t, 1, res.Count)
+		require.Len(t, res.Sessions, 1)
+		require.Equal(t, a.ID.String(), res.Sessions[0].ID)
+	})
+
+	t.Run("CursorPaginationWithTiedStartedAt", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+
+		// Create 3 standalone sessions all starting at the same time.
+		// The tie-breaker is session_id DESC.
+		for range 3 {
+			endedAt := now.Add(time.Minute)
+			dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+				InitiatorID: firstUser.UserID,
+				StartedAt:   now,
+			}, &endedAt)
+		}
+
+		// Fetch all to learn the sort order (started_at DESC,
+		// session_id DESC).
+		//nolint:gocritic // Owner role is irrelevant; testing cursor.
+		all, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{})
+		require.NoError(t, err)
+		require.Len(t, all.Sessions, 3)
+
+		// Use the first result as cursor. The remaining 2 should be
+		// returned.
+		afterID := all.Sessions[0].ID
+		page, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{
+			Pagination:     codersdk.Pagination{Limit: 10},
+			AfterSessionID: afterID,
+		})
+		require.NoError(t, err)
+		require.Len(t, page.Sessions, 2)
+		require.Equal(t, all.Sessions[1].ID, page.Sessions[0].ID)
+		require.Equal(t, all.Sessions[2].ID, page.Sessions[1].ID)
+	})
+
+	t.Run("DefaultLimit", func(t *testing.T) {
+		t.Parallel()
+		client, db, firstUser := coderdenttest.NewWithDatabase(t, aibridgeOpts(t))
+		ctx := testutil.Context(t, testutil.WaitLong)
+
+		now := dbtime.Now()
+		// Create 3 sessions. Without an explicit limit the default of
+		// 100 should apply and return all 3.
+		for i := range 3 {
+			endedAt := now.Add(-time.Duration(i)*time.Hour + time.Minute)
+			dbgen.AIBridgeInterception(t, db, database.InsertAIBridgeInterceptionParams{
+				InitiatorID: firstUser.UserID,
+				StartedAt:   now.Add(-time.Duration(i) * time.Hour),
+			}, &endedAt)
+		}
+
+		// No Pagination.Limit set.
+		//nolint:gocritic // Owner role is irrelevant; testing default limit.
+		res, err := client.AIBridgeListSessions(ctx, codersdk.AIBridgeListSessionsFilter{})
+		require.NoError(t, err)
+		require.Len(t, res.Sessions, 3)
+		require.EqualValues(t, 3, res.Count)
+	})
 }
 
 func TestAIBridgeListClients(t *testing.T) {

enterprise/coderd/exp_chats_test.go

@@ -100,7 +100,6 @@ func TestChatStreamRelay(t *testing.T) {
 			ModelConfigID: &model.ID,
 		})
 		require.NoError(t, err)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 
 		var runningChat database.Chat
 		require.Eventually(t, func() bool {
@@ -289,7 +288,6 @@ func TestChatStreamRelay(t *testing.T) {
 			ModelConfigID: &model.ID,
 		})
 		require.NoError(t, err)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 
 		var runningChat database.Chat
 		require.Eventually(t, func() bool {
@@ -459,7 +457,6 @@ func TestChatStreamRelay(t *testing.T) {
 			ModelConfigID: &model.ID,
 		})
 		require.NoError(t, err)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 
 		var runningChat database.Chat
 		require.Eventually(t, func() bool {
@@ -631,7 +628,6 @@ func TestChatStreamRelay(t *testing.T) {
 			ModelConfigID: &model.ID,
 		})
 		require.NoError(t, err)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 
 		var runningChat database.Chat
 		require.Eventually(t, func() bool {
@@ -779,7 +775,6 @@ func TestChatStreamRelay(t *testing.T) {
 			ModelConfigID: &model.ID,
 		})
 		require.NoError(t, err)
-		require.Equal(t, codersdk.ChatStatusPending, chat.Status)
 
 		var runningChat database.Chat
 		require.Eventually(t, func() bool {

enterprise/coderd/roles_test.go

@@ -452,7 +452,13 @@ func TestCustomOrganizationRole(t *testing.T) {
 func TestListRoles(t *testing.T) {
 	t.Parallel()
 
+	dv := coderdtest.DeploymentValues(t)
+	dv.Experiments = []string{string(codersdk.ExperimentAgents)}
+
 	client, owner := coderdenttest.New(t, &coderdenttest.Options{
+		Options: &coderdtest.Options{
+			DeploymentValues: dv,
+		},
 		LicenseOptions: &coderdenttest.LicenseOptions{
 			Features: license.Features{
 				codersdk.FeatureExternalProvisionerDaemons: 1,
@@ -487,6 +493,7 @@ func TestListRoles(t *testing.T) {
 				{Name: codersdk.RoleAuditor}:       false,
 				{Name: codersdk.RoleTemplateAdmin}: false,
 				{Name: codersdk.RoleUserAdmin}:     false,
+				{Name: codersdk.RoleAgentsAccess}:  false,
 			}),
 		},
 		{
@@ -520,6 +527,7 @@ func TestListRoles(t *testing.T) {
 				{Name: codersdk.RoleAuditor}:       false,
 				{Name: codersdk.RoleTemplateAdmin}: false,
 				{Name: codersdk.RoleUserAdmin}:     false,
+				{Name: codersdk.RoleAgentsAccess}:  false,
 			}),
 		},
 		{
@@ -553,6 +561,7 @@ func TestListRoles(t *testing.T) {
 				{Name: codersdk.RoleAuditor}:       true,
 				{Name: codersdk.RoleTemplateAdmin}: true,
 				{Name: codersdk.RoleUserAdmin}:     true,
+				{Name: codersdk.RoleAgentsAccess}:  true,
 			}),
 		},
 		{

enterprise/dbcrypt/cliutil.go

@@ -5,10 +5,12 @@ import (
 	"database/sql"
 	"strings"
 
+	"github.com/google/uuid"
 	"golang.org/x/xerrors"
 
 	"cdr.dev/slog/v3"
 	"github.com/coder/coder/v2/coderd/database"
+	"github.com/coder/coder/v2/coderd/database/dbtime"
 )
 
 // Rotate rotates the database encryption keys by re-encrypting all user tokens
@@ -109,6 +111,30 @@ func Rotate(ctx context.Context, log slog.Logger, sqlDB *sql.DB, ciphers []Ciphe
 		log.Debug(ctx, "encrypted chat provider key", slog.F("provider", provider.Provider), slog.F("current", idx+1), slog.F("cipher", ciphers[0].HexDigest()))
 	}
 
+	// Re-encrypt chat automation webhook secrets.
+	triggerIDs, err := fetchEncryptedTriggerIDs(ctx, sqlDB)
+	if err != nil {
+		return err
+	}
+	log.Info(ctx, "encrypting chat automation webhook secrets", slog.F("trigger_count", len(triggerIDs)))
+	for _, triggerID := range triggerIDs {
+		trigger, err := cryptDB.GetChatAutomationTriggerByID(ctx, triggerID)
+		if err != nil {
+			return xerrors.Errorf("get chat automation trigger %s: %w", triggerID, err)
+		}
+		if trigger.WebhookSecretKeyID.String == ciphers[0].HexDigest() {
+			continue // Already encrypted with the primary key.
+		}
+		if _, err := cryptDB.UpdateChatAutomationTriggerWebhookSecret(ctx, database.UpdateChatAutomationTriggerWebhookSecretParams{
+			WebhookSecret:      trigger.WebhookSecret, // decrypted by cryptDB
+			WebhookSecretKeyID: sql.NullString{},      // dbcrypt will set the new primary key
+			UpdatedAt:          dbtime.Now(),
+			ID:                 triggerID,
+		}); err != nil {
+			return xerrors.Errorf("re-encrypt chat automation trigger %s: %w", triggerID, err)
+		}
+	}
+
 	// Revoke old keys
 	for _, c := range ciphers[1:] {
 		if err := db.RevokeDBCryptKey(ctx, c.HexDigest()); err != nil {
@@ -221,6 +247,27 @@ func Decrypt(ctx context.Context, log slog.Logger, sqlDB *sql.DB, ciphers []Ciph
 		log.Debug(ctx, "decrypted chat provider key", slog.F("provider", provider.Provider), slog.F("current", idx+1), slog.F("cipher", ciphers[0].HexDigest()))
 	}
 
+	// Decrypt chat automation webhook secrets.
+	triggerIDs, err := fetchEncryptedTriggerIDs(ctx, sqlDB)
+	if err != nil {
+		return err
+	}
+	log.Info(ctx, "decrypting chat automation webhook secrets", slog.F("trigger_count", len(triggerIDs)))
+	for _, triggerID := range triggerIDs {
+		trigger, err := cryptDB.GetChatAutomationTriggerByID(ctx, triggerID)
+		if err != nil {
+			return xerrors.Errorf("get chat automation trigger %s: %w", triggerID, err)
+		}
+		if _, err := cryptDB.UpdateChatAutomationTriggerWebhookSecret(ctx, database.UpdateChatAutomationTriggerWebhookSecretParams{
+			WebhookSecret:      trigger.WebhookSecret, // decrypted by cryptDB
+			WebhookSecretKeyID: sql.NullString{},      // store in plaintext
+			UpdatedAt:          dbtime.Now(),
+			ID:                 triggerID,
+		}); err != nil {
+			return xerrors.Errorf("decrypt chat automation trigger %s: %w", triggerID, err)
+		}
+	}
+
 	// Revoke _all_ keys
 	for _, c := range ciphers {
 		if err := db.RevokeDBCryptKey(ctx, c.HexDigest()); err != nil {
@@ -245,9 +292,33 @@ UPDATE chat_providers
 	SET api_key = '',
 		api_key_key_id = NULL
 	WHERE api_key_key_id IS NOT NULL;
+DELETE FROM chat_automation_triggers WHERE webhook_secret_key_id IS NOT NULL;
 COMMIT;
 `
 
+// fetchEncryptedTriggerIDs returns the IDs of all chat automation
+// triggers that have an encrypted webhook secret. It uses a raw
+// SQL query because there is no "get all triggers" SQLC query.
+func fetchEncryptedTriggerIDs(ctx context.Context, sqlDB *sql.DB) ([]uuid.UUID, error) {
+	rows, err := sqlDB.QueryContext(ctx, `SELECT id FROM chat_automation_triggers WHERE webhook_secret_key_id IS NOT NULL`)
+	if err != nil {
+		return nil, xerrors.Errorf("get encrypted chat automation triggers: %w", err)
+	}
+	defer rows.Close()
+	var ids []uuid.UUID
+	for rows.Next() {
+		var id uuid.UUID
+		if err := rows.Scan(&id); err != nil {
+			return nil, xerrors.Errorf("scan chat automation trigger id: %w", err)
+		}
+		ids = append(ids, id)
+	}
+	if err := rows.Err(); err != nil {
+		return nil, xerrors.Errorf("iterate chat automation trigger ids: %w", err)
+	}
+	return ids, nil
+}
+
 // Delete deletes all user tokens and revokes all ciphers.
 // This is a destructive operation and should only be used
 // as a last resort, for example, if the database encryption key has been
@@ -256,9 +327,9 @@ func Delete(ctx context.Context, log slog.Logger, sqlDB *sql.DB) error {
 	store := database.New(sqlDB)
 	_, err := sqlDB.ExecContext(ctx, sqlDeleteEncryptedUserTokens)
 	if err != nil {
-		return xerrors.Errorf("delete encrypted tokens and chat provider keys: %w", err)
+		return xerrors.Errorf("delete encrypted tokens, chat provider keys, and chat automation webhook secrets: %w", err)
 	}
-	log.Info(ctx, "deleted encrypted user tokens and chat provider API keys")
+	log.Info(ctx, "deleted encrypted user tokens, chat provider API keys, and chat automation webhook secrets")
 
 	log.Info(ctx, "revoking all active keys")
 	keys, err := store.GetDBCryptKeys(ctx)

enterprise/dbcrypt/dbcrypt.go

@@ -385,6 +385,73 @@ func (db *dbCrypt) GetCryptoKeysByFeature(ctx context.Context, feature database.
 	return keys, nil
 }
 
+func (db *dbCrypt) GetChatAutomationTriggerByID(ctx context.Context, id uuid.UUID) (database.ChatAutomationTrigger, error) {
+	trigger, err := db.Store.GetChatAutomationTriggerByID(ctx, id)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := db.decryptField(&trigger.WebhookSecret.String, trigger.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return trigger, nil
+}
+
+func (db *dbCrypt) GetChatAutomationTriggersByAutomationID(ctx context.Context, automationID uuid.UUID) ([]database.ChatAutomationTrigger, error) {
+	triggers, err := db.Store.GetChatAutomationTriggersByAutomationID(ctx, automationID)
+	if err != nil {
+		return nil, err
+	}
+	for i := range triggers {
+		if err := db.decryptField(&triggers[i].WebhookSecret.String, triggers[i].WebhookSecretKeyID); err != nil {
+			return nil, err
+		}
+	}
+	return triggers, nil
+}
+
+func (db *dbCrypt) InsertChatAutomationTrigger(ctx context.Context, params database.InsertChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	if !params.WebhookSecret.Valid || strings.TrimSpace(params.WebhookSecret.String) == "" {
+		params.WebhookSecretKeyID = sql.NullString{}
+	} else if err := db.encryptField(&params.WebhookSecret.String, &params.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	trigger, err := db.Store.InsertChatAutomationTrigger(ctx, params)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := db.decryptField(&trigger.WebhookSecret.String, trigger.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return trigger, nil
+}
+
+func (db *dbCrypt) UpdateChatAutomationTrigger(ctx context.Context, params database.UpdateChatAutomationTriggerParams) (database.ChatAutomationTrigger, error) {
+	trigger, err := db.Store.UpdateChatAutomationTrigger(ctx, params)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := db.decryptField(&trigger.WebhookSecret.String, trigger.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return trigger, nil
+}
+
+func (db *dbCrypt) UpdateChatAutomationTriggerWebhookSecret(ctx context.Context, params database.UpdateChatAutomationTriggerWebhookSecretParams) (database.ChatAutomationTrigger, error) {
+	if !params.WebhookSecret.Valid || strings.TrimSpace(params.WebhookSecret.String) == "" {
+		params.WebhookSecretKeyID = sql.NullString{}
+	} else if err := db.encryptField(&params.WebhookSecret.String, &params.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	trigger, err := db.Store.UpdateChatAutomationTriggerWebhookSecret(ctx, params)
+	if err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	if err := db.decryptField(&trigger.WebhookSecret.String, trigger.WebhookSecretKeyID); err != nil {
+		return database.ChatAutomationTrigger{}, err
+	}
+	return trigger, nil
+}
+
 func (db *dbCrypt) GetChatProviderByID(ctx context.Context, id uuid.UUID) (database.ChatProvider, error) {
 	provider, err := db.Store.GetChatProviderByID(ctx, id)
 	if err != nil {

enterprise/dbcrypt/dbcrypt_internal_test.go

@@ -1177,3 +1177,196 @@ func TestMCPServerUserTokens(t *testing.T) {
 		requireEncryptedEquals(t, ciphers[0], rawTok.RefreshToken, refreshToken)
 	})
 }
+
+func TestChatAutomationTriggers(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+
+	const (
+		//nolint:gosec // test credential
+		webhookSecret = "whsec-test-secret-value"
+	)
+
+	// insertTrigger creates a user, organization, chat automation, and
+	// a webhook trigger with a secret through the encrypted store.
+	insertTrigger := func(t *testing.T, crypt *dbCrypt, ciphers []Cipher) database.ChatAutomationTrigger {
+		t.Helper()
+		user := dbgen.User(t, crypt, database.User{})
+		org := dbgen.Organization(t, crypt, database.Organization{})
+		now := dbtime.Now()
+		automation, err := crypt.InsertChatAutomation(ctx, database.InsertChatAutomationParams{
+			ID:                    uuid.New(),
+			OwnerID:               user.ID,
+			OrganizationID:        org.ID,
+			Name:                  "test-automation-" + uuid.New().String()[:8],
+			Description:           "test automation",
+			Instructions:          "do stuff",
+			MCPServerIDs:          []uuid.UUID{},
+			AllowedTools:          []string{},
+			Status:                database.ChatAutomationStatusActive,
+			MaxChatCreatesPerHour: 10,
+			MaxMessagesPerHour:    60,
+			CreatedAt:             now,
+			UpdatedAt:             now,
+		})
+		require.NoError(t, err)
+
+		trigger, err := crypt.InsertChatAutomationTrigger(ctx, database.InsertChatAutomationTriggerParams{
+			ID:            uuid.New(),
+			AutomationID:  automation.ID,
+			Type:          database.ChatAutomationTriggerTypeWebhook,
+			WebhookSecret: sql.NullString{String: webhookSecret, Valid: true},
+			CreatedAt:     now,
+			UpdatedAt:     now,
+		})
+		require.NoError(t, err)
+		require.Equal(t, webhookSecret, trigger.WebhookSecret.String)
+		require.Equal(t, ciphers[0].HexDigest(), trigger.WebhookSecretKeyID.String)
+		return trigger
+	}
+
+	// requireTriggerRawEncrypted reads the trigger from the raw
+	// (unwrapped) store and asserts the secret field is encrypted.
+	requireTriggerRawEncrypted := func(
+		t *testing.T,
+		rawDB database.Store,
+		triggerID uuid.UUID,
+		ciphers []Cipher,
+		wantSecret string,
+	) {
+		t.Helper()
+		raw, err := rawDB.GetChatAutomationTriggerByID(ctx, triggerID)
+		require.NoError(t, err)
+		requireEncryptedEquals(t, ciphers[0], raw.WebhookSecret.String, wantSecret)
+	}
+
+	t.Run("InsertChatAutomationTrigger", func(t *testing.T) {
+		t.Parallel()
+		db, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+		requireTriggerRawEncrypted(t, db, trigger.ID, ciphers, webhookSecret)
+	})
+
+	t.Run("GetChatAutomationTriggerByID", func(t *testing.T) {
+		t.Parallel()
+		db, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		got, err := crypt.GetChatAutomationTriggerByID(ctx, trigger.ID)
+		require.NoError(t, err)
+		require.Equal(t, webhookSecret, got.WebhookSecret.String)
+		require.Equal(t, ciphers[0].HexDigest(), got.WebhookSecretKeyID.String)
+		requireTriggerRawEncrypted(t, db, trigger.ID, ciphers, webhookSecret)
+	})
+
+	t.Run("GetChatAutomationTriggersByAutomationID", func(t *testing.T) {
+		t.Parallel()
+		db, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		triggers, err := crypt.GetChatAutomationTriggersByAutomationID(ctx, trigger.AutomationID)
+		require.NoError(t, err)
+		require.Len(t, triggers, 1)
+		require.Equal(t, webhookSecret, triggers[0].WebhookSecret.String)
+		require.Equal(t, ciphers[0].HexDigest(), triggers[0].WebhookSecretKeyID.String)
+		requireTriggerRawEncrypted(t, db, trigger.ID, ciphers, webhookSecret)
+	})
+
+	t.Run("UpdateChatAutomationTrigger", func(t *testing.T) {
+		t.Parallel()
+		db, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		// UpdateChatAutomationTrigger does not change the webhook
+		// secret itself; it updates cron_schedule/filter/label_paths.
+		// The returned trigger should still have the decrypted secret.
+		updated, err := crypt.UpdateChatAutomationTrigger(ctx, database.UpdateChatAutomationTriggerParams{
+			ID:        trigger.ID,
+			UpdatedAt: dbtime.Now(),
+		})
+		require.NoError(t, err)
+		require.Equal(t, webhookSecret, updated.WebhookSecret.String)
+		require.Equal(t, ciphers[0].HexDigest(), updated.WebhookSecretKeyID.String)
+		requireTriggerRawEncrypted(t, db, trigger.ID, ciphers, webhookSecret)
+	})
+
+	t.Run("UpdateChatAutomationTriggerWebhookSecret", func(t *testing.T) {
+		t.Parallel()
+		db, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		const newSecret = "whsec-rotated-secret" //nolint:gosec // test credential
+		updated, err := crypt.UpdateChatAutomationTriggerWebhookSecret(ctx, database.UpdateChatAutomationTriggerWebhookSecretParams{
+			ID:            trigger.ID,
+			WebhookSecret: sql.NullString{String: newSecret, Valid: true},
+			UpdatedAt:     dbtime.Now(),
+		})
+		require.NoError(t, err)
+		require.Equal(t, newSecret, updated.WebhookSecret.String)
+		require.Equal(t, ciphers[0].HexDigest(), updated.WebhookSecretKeyID.String)
+		requireTriggerRawEncrypted(t, db, trigger.ID, ciphers, newSecret)
+	})
+
+	t.Run("CronTriggerThroughDecryptLoop", func(t *testing.T) {
+		t.Parallel()
+		_, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		// Insert a cron trigger under the same automation. Cron
+		// triggers have no webhook secret, so the secret fields
+		// should remain NULL through the encrypt/decrypt loop.
+		now := dbtime.Now()
+		cronTrigger, err := crypt.InsertChatAutomationTrigger(ctx, database.InsertChatAutomationTriggerParams{
+			ID:            uuid.New(),
+			AutomationID:  trigger.AutomationID,
+			Type:          database.ChatAutomationTriggerTypeCron,
+			CronSchedule:  sql.NullString{String: "0 * * * *", Valid: true},
+			WebhookSecret: sql.NullString{Valid: false},
+			CreatedAt:     now,
+			UpdatedAt:     now,
+		})
+		require.NoError(t, err)
+		require.False(t, cronTrigger.WebhookSecret.Valid)
+		require.False(t, cronTrigger.WebhookSecretKeyID.Valid)
+
+		// Fetch both triggers by automation ID and verify each
+		// comes back with the expected secret state.
+		triggers, err := crypt.GetChatAutomationTriggersByAutomationID(ctx, trigger.AutomationID)
+		require.NoError(t, err)
+		require.Len(t, triggers, 2)
+
+		for _, tr := range triggers {
+			switch tr.Type {
+			case database.ChatAutomationTriggerTypeWebhook:
+				require.Equal(t, webhookSecret, tr.WebhookSecret.String)
+				require.Equal(t, ciphers[0].HexDigest(), tr.WebhookSecretKeyID.String)
+			case database.ChatAutomationTriggerTypeCron:
+				require.False(t, tr.WebhookSecret.Valid, "cron trigger should have NULL secret")
+				require.False(t, tr.WebhookSecretKeyID.Valid, "cron trigger should have NULL key_id")
+				require.Equal(t, "0 * * * *", tr.CronSchedule.String)
+			default:
+				t.Fatalf("unexpected trigger type: %s", tr.Type)
+			}
+		}
+	})
+
+	t.Run("ClearWebhookSecretToNULL", func(t *testing.T) {
+		t.Parallel()
+		_, crypt, ciphers := setup(t)
+		trigger := insertTrigger(t, crypt, ciphers)
+
+		// The DB schema enforces that webhook-type triggers must
+		// always have a non-NULL webhook_secret via the
+		// chat_automation_triggers_webhook_fields constraint.
+		// Attempting to clear it to NULL should fail. This verifies
+		// the dbcrypt layer correctly clears the key_id and passes
+		// the NULL through to the DB, which then rejects it.
+		_, err := crypt.UpdateChatAutomationTriggerWebhookSecret(ctx, database.UpdateChatAutomationTriggerWebhookSecretParams{
+			ID:            trigger.ID,
+			WebhookSecret: sql.NullString{Valid: false},
+			UpdatedAt:     dbtime.Now(),
+		})
+		require.Error(t, err)
+		require.Contains(t, err.Error(), "chat_automation_triggers_webhook_fields")
+	})
+}

go.mod

@@ -1,6 +1,6 @@
 module github.com/coder/coder/v2
 
-go 1.25.7
+go 1.25.8
 
 // Required until a v3 of chroma is created to lazily initialize all XML files.
 // None of our dependencies seem to use the registries anyways, so this
@@ -483,7 +483,7 @@ require (
 	github.com/anthropics/anthropic-sdk-go v1.19.0
 	github.com/brianvoe/gofakeit/v7 v7.14.0
 	github.com/coder/agentapi-sdk-go v0.0.0-20250505131810-560d1d88d225
-	github.com/coder/aibridge v1.0.8-0.20260324203533-dd8c239e5566
+	github.com/coder/aibridge v1.1.1-0.20260331154949-a011104f377d
 	github.com/coder/aisdk-go v0.0.9
 	github.com/coder/boundary v0.8.4-0.20260304164748-566aeea939ab
 	github.com/coder/preview v1.0.8
@@ -491,7 +491,7 @@ require (
 	github.com/dgraph-io/ristretto/v2 v2.4.0
 	github.com/elazarl/goproxy v1.8.0
 	github.com/fsnotify/fsnotify v1.9.0
-	github.com/go-git/go-git/v5 v5.17.0
+	github.com/go-git/go-git/v5 v5.17.1
 	github.com/mark3labs/mcp-go v0.38.0
 	github.com/shopspring/decimal v1.4.0
 	gonum.org/v1/gonum v0.17.0

go.sum

@@ -314,8 +314,8 @@ github.com/cncf/xds/go v0.0.0-20260202195803-dba9d589def2 h1:aBangftG7EVZoUb69Os
 github.com/cncf/xds/go v0.0.0-20260202195803-dba9d589def2/go.mod h1:qwXFYgsP6T7XnJtbKlf1HP8AjxZZyzxMmc+Lq5GjlU4=
 github.com/coder/agentapi-sdk-go v0.0.0-20250505131810-560d1d88d225 h1:tRIViZ5JRmzdOEo5wUWngaGEFBG8OaE1o2GIHN5ujJ8=
 github.com/coder/agentapi-sdk-go v0.0.0-20250505131810-560d1d88d225/go.mod h1:rNLVpYgEVeu1Zk29K64z6Od8RBP9DwqCu9OfCzh8MR4=
-github.com/coder/aibridge v1.0.8-0.20260324203533-dd8c239e5566 h1:DK+a7Q9bPpTyq7ePaz81Ihauyp1ilXNhF8MI+7rmZpA=
-github.com/coder/aibridge v1.0.8-0.20260324203533-dd8c239e5566/go.mod h1:u6WvGLMQQbk3ByeOw+LBdVgDNc/v/ujAtUc6MfvzQb4=
+github.com/coder/aibridge v1.1.1-0.20260331154949-a011104f377d h1:yoDGndlvKP6fiKzivG7kYLYs7jDEt2phgGVagDmuAHY=
+github.com/coder/aibridge v1.1.1-0.20260331154949-a011104f377d/go.mod h1:u6WvGLMQQbk3ByeOw+LBdVgDNc/v/ujAtUc6MfvzQb4=
 github.com/coder/aisdk-go v0.0.9 h1:Vzo/k2qwVGLTR10ESDeP2Ecek1SdPfZlEjtTfMveiVo=
 github.com/coder/aisdk-go v0.0.9/go.mod h1:KF6/Vkono0FJJOtWtveh5j7yfNrSctVTpwgweYWSp5M=
 github.com/coder/boundary v0.8.4-0.20260304164748-566aeea939ab h1:HrlxyTmMQpOHfSKzRU1vf5TxrmV6vL5OiWq+Dvn5qh0=
@@ -516,8 +516,8 @@ github.com/go-git/gcfg v1.5.1-0.20230307220236-3a3c6141e376 h1:+zs/tPmkDkHx3U66D
 github.com/go-git/gcfg v1.5.1-0.20230307220236-3a3c6141e376/go.mod h1:an3vInlBmSxCcxctByoQdvwPiA7DTK7jaaFDBTtu0ic=
 github.com/go-git/go-billy/v5 v5.8.0 h1:I8hjc3LbBlXTtVuFNJuwYuMiHvQJDq1AT6u4DwDzZG0=
 github.com/go-git/go-billy/v5 v5.8.0/go.mod h1:RpvI/rw4Vr5QA+Z60c6d6LXH0rYJo0uD5SqfmrrheCY=
-github.com/go-git/go-git/v5 v5.17.0 h1:AbyI4xf+7DsjINHMu35quAh4wJygKBKBuXVjV/pxesM=
-github.com/go-git/go-git/v5 v5.17.0/go.mod h1:f82C4YiLx+Lhi8eHxltLeGC5uBTXSFa6PC5WW9o4SjI=
+github.com/go-git/go-git/v5 v5.17.1 h1:WnljyxIzSj9BRRUlnmAU35ohDsjRK0EKmL0evDqi5Jk=
+github.com/go-git/go-git/v5 v5.17.1/go.mod h1:pW/VmeqkanRFqR6AljLcs7EA7FbZaN5MQqO7oZADXpo=
 github.com/go-ini/ini v1.67.0 h1:z6ZrTEZqSWOTyH2FlglNbNgARyHG8oLW9gMELqKr06A=
 github.com/go-ini/ini v1.67.0/go.mod h1:ByCAeIL28uOIIG0E3PJtZPDL8WnHpFKFOtgjp+3Ies8=
 github.com/go-jose/go-jose/v4 v4.1.3 h1:CVLmWDhDVRa6Mi/IgCgaopNosCaHz7zrMeF9MlZRkrs=

site/permissions.json

@@ -118,5 +118,9 @@
 	"viewOAuth2AppSecrets": {
 		"object": { "resource_type": "oauth2_app_secret" },
 		"action": "read"
+	},
+	"createChat": {
+		"object": { "resource_type": "chat", "owner_id": "me" },
+		"action": "create"
 	}
 }

site/scripts/check-compiler.mjs

@@ -1,18 +1,56 @@
+/**
+ * React Compiler diagnostic checker.
+ *
+ * Runs babel-plugin-react-compiler over every .ts/.tsx file in the
+ * target directories and reports functions that failed to compile or
+ * were skipped. Exits with code 1 when any diagnostics are present
+ * or a target directory is missing.
+ *
+ * Usage:  node scripts/check-compiler.mjs
+ */
 import { readFileSync, readdirSync } from "node:fs";
 import { join, relative } from "node:path";
+import { fileURLToPath } from "node:url";
 import { transformSync } from "@babel/core";
 
+// Resolve the site/ directory (ESM equivalent of __dirname + "..").
 const siteDir = new URL("..", import.meta.url).pathname;
 
+// Only AgentsPage is currently opted in to React Compiler. Add new
+// directories here as more pages are migrated.
 const targetDirs = [
 	"src/pages/AgentsPage",
 ];
 
 const skipPatterns = [".test.", ".stories.", ".jest."];
 
+// Maximum length for truncated error messages in the report.
+const MAX_ERROR_LENGTH = 120;
+
+// ---------------------------------------------------------------------------
+// File collection
+// ---------------------------------------------------------------------------
+
+/**
+ * Recursively collect .ts/.tsx files under `dir`, skipping test and
+ * story files. Returns paths relative to `siteDir`. Sets
+ * `hadCollectionErrors` and returns an empty array on ENOENT so the
+ * caller and recursive calls both stay safe.
+ */
 function collectFiles(dir) {
+	let entries;
+	try {
+		entries = readdirSync(dir, { withFileTypes: true });
+	} catch (e) {
+		if (e.code === "ENOENT") {
+			console.error(`Target directory not found: ${relative(siteDir, dir)}`);
+			hadCollectionErrors = true;
+			return [];
+		}
+		throw e;
+	}
 	const results = [];
-	for (const entry of readdirSync(dir, { withFileTypes: true })) {
+	for (const entry of entries) {
 		const full = join(dir, entry.name);
 		if (entry.isDirectory()) {
 			results.push(...collectFiles(full));
@@ -26,17 +64,63 @@ function collectFiles(dir) {
 	return results;
 }
 
-const files = targetDirs.flatMap((d) => collectFiles(join(siteDir, d)));
+// ---------------------------------------------------------------------------
+// Compilation & diagnostics
+//
+// We use transformSync deliberately. The React Compiler plugin is
+// CPU-bound (parse-only takes ~2s vs ~19s with the compiler over all
+// of site/src), so transformAsync + Promise.all gives no speedup —
+// Node still runs all transforms on a single thread. Benchmarked
+// sync, async-sequential, and async-parallel: all land within noise
+// of each other. The sync API keeps the code simple.
+// ---------------------------------------------------------------------------
 
-let totalCompiled = 0;
-const failures = [];
+/**
+ * Shorten a compiler diagnostic message to its first sentence, stripping
+ * the leading "Error: " prefix and any trailing URL references so the
+ * one-line report stays readable.
+ *
+ * Example:
+ *   "Error: Ref values are not allowed. Use ref types instead (https://…)."
+ *   → "Ref values are not allowed"
+ */
+export function shortenMessage(msg) {
+	const str = typeof msg === "string" ? msg : String(msg);
+	return str
+		.replace(/^Error: /, "")
+		.split(/\.\s/)[0]
+		.split("(http")[0]
+		.replace(/\.\s*$/, "")
+		.trim();
+}
 
-for (const file of files) {
-	const code = readFileSync(join(siteDir, file), "utf-8");
+/**
+ * Remove diagnostics that share the same line + message. The compiler
+ * can emit duplicate events for the same function when it retries
+ * compilation, so we deduplicate before reporting.
+ */
+export function deduplicateDiagnostics(diagnostics) {
+	const seen = new Set();
+	return diagnostics.filter((d) => {
+		const key = `${d.line}:${d.short}`;
+		if (seen.has(key)) return false;
+		seen.add(key);
+		return true;
+	});
+}
+
+/**
+ * Run the React Compiler over a single file and return the number of
+ * successfully compiled functions plus any diagnostics. Transform
+ * errors are caught and returned as a diagnostic with line 0 rather
+ * than thrown, so the caller always gets a result.
+ */
+function compileFile(file) {
 	const isTSX = file.endsWith(".tsx");
 	const diagnostics = [];
 
 	try {
+		const code = readFileSync(join(siteDir, file), "utf-8");
 		const result = transformSync(code, {
 			plugins: [
 				["@babel/plugin-syntax-typescript", { isTSX }],
@@ -44,53 +128,105 @@ for (const file of files) {
 					logger: {
 						logEvent(_filename, event) {
 							if (event.kind === "CompileError" || event.kind === "CompileSkip") {
-								const msg = event.detail || event.reason || "";
-								const short = typeof msg === "string"
-									? msg.replace(/^Error: /, "").split(".")[0].split("(http")[0].trim()
-									: String(msg);
-								diagnostics.push({ line: event.fnLoc?.start?.line, short });
+								const msg = event.detail || event.reason || "(unknown)";
+								diagnostics.push({
+									line: event.fnLoc?.start?.line ?? 0,
+									short: shortenMessage(msg),
+								});
 							}
 						},
 					},
 				}],
 			],
 			filename: file,
+			// Skip config-file resolution. No babel.config.js exists in the
+			// repo, so the search is wasted I/O on every file.
+			configFile: false,
+			babelrc: false,
 		});
 
-		const slots = result.code.match(/const \$ = _c\(\d+\)/g) || [];
-		totalCompiled += slots.length;
+		// The compiler inserts `const $ = _c(N)` at the top of every
+		// function it successfully compiles, where N is the number of
+		// memoization slots. Counting these tells us how many functions
+		// were compiled in this file.
+		const compiledCount = result?.code?.match(/const \$ = _c\(\d+\)/g)?.length ?? 0;
 
-		if (diagnostics.length) {
-			const seen = new Set();
-			const unique = diagnostics.filter((d) => {
-				const key = `${d.line}:${d.short}`;
-				if (seen.has(key)) return false;
-				seen.add(key);
-				return true;
-			});
-			failures.push({ file, compiled: slots.length, diagnostics: unique });
-		}
+		return {
+			compiled: compiledCount,
+			diagnostics: deduplicateDiagnostics(diagnostics),
+		};
 	} catch (e) {
-		failures.push({
-			file, compiled: 0,
-			diagnostics: [{ line: 0, short: `Transform error: ${String(e.message).substring(0, 120)}` }],
-		});
+		return {
+			compiled: 0,
+			diagnostics: [{
+				line: 0,
+				// Truncate to keep the one-line report readable.
+				short: `Transform error: ${(e instanceof Error ? e.message : String(e)).substring(0, MAX_ERROR_LENGTH)}`,
+			}],
+		};
 	}
 }
 
-console.log(`\nTotal: ${totalCompiled} functions compiled across ${files.length} files`);
-console.log(`Files with diagnostics: ${failures.length}\n`);
+// ---------------------------------------------------------------------------
+// Report
+// ---------------------------------------------------------------------------
 
-for (const f of failures) {
-	const short = f.file.replace("src/pages/AgentsPage/", "");
-	console.log(`✗ ${short} (${f.compiled} compiled)`);
-	for (const d of f.diagnostics) {
-		console.log(`    line ${d.line}: ${d.short}`);
+/**
+ * Derive a short display path by stripping the first matching target
+ * dir prefix so the output stays compact.
+ */
+export function shortPath(file, dirs = targetDirs) {
+	for (const dir of dirs) {
+		const prefix = `${dir}/`;
+		if (file.startsWith(prefix)) {
+			return file.slice(prefix.length);
+		}
+	}
+	return file;
+}
+
+/** Print a summary of compilation results and per-file diagnostics. */
+function printReport(failures, totalCompiled, fileCount, hadErrors) {
+	console.log(`\nTotal: ${totalCompiled} functions compiled across ${fileCount} files`);
+	console.log(`Files with diagnostics: ${failures.length}\n`);
+
+	for (const f of failures) {
+		console.log(`✗ ${shortPath(f.file)} (${f.compiled} compiled)`);
+		for (const d of f.diagnostics) {
+			console.log(`    line ${d.line}: ${d.short}`);
+		}
+	}
+
+	if (failures.length === 0 && !hadErrors) {
+		console.log("✓ All files compile cleanly.");
 	}
 }
 
-if (failures.length === 0) {
-	console.log("✓ All files compile cleanly.");
-} else {
+// ---------------------------------------------------------------------------
+// Main
+// ---------------------------------------------------------------------------
+
+// Only run the main block when executed directly, not when imported
+// by tests for the exported pure functions.
+if (process.argv[1] === fileURLToPath(import.meta.url)) {
+	let hadCollectionErrors = false;
+
+	const files = targetDirs.flatMap((d) => collectFiles(join(siteDir, d)));
+
+let totalCompiled = 0;
+const failures = [];
+
+for (const file of files) {
+	const { compiled, diagnostics } = compileFile(file);
+	totalCompiled += compiled;
+	if (diagnostics.length > 0) {
+		failures.push({ file, compiled, diagnostics });
+	}
+}
+
+printReport(failures, totalCompiled, files.length, hadCollectionErrors);
+
+if (failures.length > 0 || hadCollectionErrors) {
 	process.exitCode = 1;
 }
+}

site/scripts/check-compiler.test.mjs

@@ -0,0 +1,95 @@
+import { describe, expect, it } from "vitest";
+import {
+	deduplicateDiagnostics,
+	shortPath,
+	shortenMessage,
+} from "./check-compiler.mjs";
+
+describe("shortenMessage", () => {
+	it("strips Error: prefix and takes first sentence", () => {
+		expect(
+			shortenMessage(
+				"Error: Ref values are not allowed. Use ref types instead.",
+			),
+		).toBe("Ref values are not allowed");
+	});
+
+	it("strips trailing URL references", () => {
+		expect(
+			shortenMessage("Mutating a value returned from a hook(https://react.dev/reference)"),
+		).toBe("Mutating a value returned from a hook");
+	});
+
+	it("preserves dotted property paths", () => {
+		expect(
+			shortenMessage("Cannot destructure props.foo because it is null"),
+		).toBe("Cannot destructure props.foo because it is null");
+	});
+
+	it("coerces non-string values", () => {
+		expect(shortenMessage(42)).toBe("42");
+		expect(shortenMessage({ toString: () => "Error: obj. detail" })).toBe("obj");
+	});
+
+	it("normalizes trailing periods", () => {
+		expect(shortenMessage("Single sentence.")).toBe("Single sentence");
+	});
+
+	it("preserves empty string and (unknown) sentinel", () => {
+		expect(shortenMessage("")).toBe("");
+		expect(shortenMessage("(unknown)")).toBe("(unknown)");
+	});
+});
+
+describe("deduplicateDiagnostics", () => {
+	it("removes duplicates with same line and message", () => {
+		const input = [
+			{ line: 1, short: "error A" },
+			{ line: 1, short: "error A" },
+			{ line: 2, short: "error B" },
+		];
+		expect(deduplicateDiagnostics(input)).toEqual([
+			{ line: 1, short: "error A" },
+			{ line: 2, short: "error B" },
+		]);
+	});
+
+	it("keeps diagnostics with same message on different lines", () => {
+		const input = [
+			{ line: 1, short: "error A" },
+			{ line: 2, short: "error A" },
+		];
+		expect(deduplicateDiagnostics(input)).toEqual(input);
+	});
+
+	it("keeps diagnostics with same line but different messages", () => {
+		const input = [
+			{ line: 1, short: "error A" },
+			{ line: 1, short: "error B" },
+		];
+		expect(deduplicateDiagnostics(input)).toEqual(input);
+	});
+
+	it("returns empty array for empty input", () => {
+		expect(deduplicateDiagnostics([])).toEqual([]);
+	});
+});
+
+describe("shortPath", () => {
+	const dirs = ["src/pages/AgentsPage", "src/pages/Other"];
+
+	it("strips matching target dir prefix", () => {
+		expect(shortPath("src/pages/AgentsPage/components/Chat.tsx", dirs))
+			.toBe("components/Chat.tsx");
+	});
+
+	it("strips first matching prefix when multiple match", () => {
+		expect(shortPath("src/pages/Other/index.tsx", dirs))
+			.toBe("index.tsx");
+	});
+
+	it("returns file unchanged when no prefix matches", () => {
+		expect(shortPath("src/utils/helper.ts", dirs))
+			.toBe("src/utils/helper.ts");
+	});
+});

site/site.go

@@ -571,9 +571,16 @@ func init() {
 func (h *Handler) renderPermissions(ctx context.Context, actor rbac.Subject) string {
 	response := make(codersdk.AuthorizationResponse)
 	for k, v := range permissionChecks {
+		// Resolve the "me" sentinel so permission checks
+		// run against the actual actor, matching the
+		// API-side handling in coderd/authorize.go.
+		ownerID := v.Object.OwnerID
+		if ownerID == codersdk.Me {
+			ownerID = actor.ID
+		}
 		obj := rbac.Object{
 			ID:          v.Object.ResourceID,
-			Owner:       v.Object.OwnerID,
+			Owner:       ownerID,
 			OrgID:       v.Object.OrganizationID,
 			AnyOrgOwner: v.Object.AnyOrgOwner,
 			Type:        string(v.Object.ResourceType),

site/site_test.go

@@ -21,6 +21,7 @@ import (
 	"github.com/go-chi/chi/v5"
 	"github.com/go-chi/chi/v5/middleware"
 	"github.com/google/uuid"
+	"github.com/prometheus/client_golang/prometheus"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
 	"golang.org/x/exp/maps"
@@ -31,6 +32,7 @@ import (
 	"github.com/coder/coder/v2/coderd/database/dbtestutil"
 	"github.com/coder/coder/v2/coderd/database/dbtime"
 	"github.com/coder/coder/v2/coderd/httpmw"
+	"github.com/coder/coder/v2/coderd/rbac"
 	"github.com/coder/coder/v2/coderd/telemetry"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/site"
@@ -79,6 +81,74 @@ func TestInjection(t *testing.T) {
 	require.Equal(t, db2sdk.User(user, []uuid.UUID{}), got)
 }
 
+func TestRenderPermissionsResolvesMe(t *testing.T) {
+	t.Parallel()
+
+	// GIVEN: a site handler wired to a real RBAC authorizer and a
+	// template that renders only the SSR permissions JSON.
+	siteFS := fstest.MapFS{
+		"index.html": &fstest.MapFile{
+			Data: []byte("{{ .Permissions }}"),
+		},
+	}
+	db, _ := dbtestutil.NewDB(t)
+	authorizer := rbac.NewStrictCachingAuthorizer(prometheus.NewRegistry())
+
+	handler, err := site.New(&site.Options{
+		Telemetry:  telemetry.NewNoop(),
+		Database:   db,
+		SiteFS:     siteFS,
+		Authorizer: authorizer,
+	})
+	require.NoError(t, err)
+
+	// GIVEN: a user with the agents-access role.
+	userWithRole := dbgen.User(t, db, database.User{
+		RBACRoles: []string{"agents-access"},
+	})
+	_, tokenWithRole := dbgen.APIKey(t, db, database.APIKey{
+		UserID:    userWithRole.ID,
+		ExpiresAt: time.Now().Add(time.Hour),
+	})
+
+	// WHEN: the user loads the page.
+	r := httptest.NewRequest("GET", "/", nil)
+	r.Header.Set(codersdk.SessionTokenHeader, tokenWithRole)
+	rw := httptest.NewRecorder()
+	handler.ServeHTTP(rw, r)
+	require.Equal(t, http.StatusOK, rw.Code)
+
+	// THEN: the SSR-rendered permissions include createChat = true
+	// because the "me" sentinel in permissions.json was resolved to
+	// the actor's ID, and the agents-access role grants user-scoped
+	// chat create permission.
+	var permsWithRole codersdk.AuthorizationResponse
+	err = json.Unmarshal([]byte(html.UnescapeString(rw.Body.String())), &permsWithRole)
+	require.NoError(t, err)
+	assert.True(t, permsWithRole["createChat"], "user with agents-access role should have createChat = true")
+
+	// GIVEN: a user without the agents-access role.
+	userWithoutRole := dbgen.User(t, db, database.User{})
+	_, tokenWithoutRole := dbgen.APIKey(t, db, database.APIKey{
+		UserID:    userWithoutRole.ID,
+		ExpiresAt: time.Now().Add(time.Hour),
+	})
+
+	// WHEN: the user loads the page.
+	r = httptest.NewRequest("GET", "/", nil)
+	r.Header.Set(codersdk.SessionTokenHeader, tokenWithoutRole)
+	rw = httptest.NewRecorder()
+	handler.ServeHTTP(rw, r)
+	require.Equal(t, http.StatusOK, rw.Code)
+
+	// THEN: createChat = false because the member role does not
+	// grant chat permissions.
+	var permsWithoutRole codersdk.AuthorizationResponse
+	err = json.Unmarshal([]byte(html.UnescapeString(rw.Body.String())), &permsWithoutRole)
+	require.NoError(t, err)
+	assert.False(t, permsWithoutRole["createChat"], "user without agents-access role should have createChat = false")
+}
+
 func TestInjectionFailureProducesCleanHTML(t *testing.T) {
 	t.Parallel()
 

site/src/api/errors.ts

@@ -1,11 +1,5 @@
 import { type AxiosError, type AxiosResponse, isAxiosError } from "axios";
 
-const Language = {
-	errorsByCode: {
-		defaultErrorCode: "Invalid value",
-	},
-};
-
 export interface FieldError {
 	field: string;
 	detail: string;
@@ -64,8 +58,7 @@ export const mapApiErrorToFieldErrors = (
 
 	if (apiErrorResponse.validations) {
 		for (const error of apiErrorResponse.validations) {
-			result[error.field] =
-				error.detail || Language.errorsByCode.defaultErrorCode;
+			result[error.field] = error.detail || "Invalid value";
 		}
 	}
 

site/src/api/rbacresourcesGenerated.ts

@@ -47,6 +47,12 @@ export const RBACResourceActions: Partial<
 		read: "read chat messages and metadata",
 		update: "update chat title or settings",
 	},
+	chat_automation: {
+		create: "create a chat automation",
+		delete: "delete a chat automation",
+		read: "read chat automation configuration",
+		update: "update a chat automation",
+	},
 	connection_log: {
 		read: "read connection logs",
 		update: "upsert connection log entries",

site/src/api/typesGenerated.ts

@@ -320,6 +320,11 @@ export type APIKeyScope =
 	| "boundary_usage:read"
 	| "boundary_usage:update"
 	| "chat:*"
+	| "chat_automation:*"
+	| "chat_automation:create"
+	| "chat_automation:delete"
+	| "chat_automation:read"
+	| "chat_automation:update"
 	| "chat:create"
 	| "chat:delete"
 	| "chat:read"
@@ -529,6 +534,11 @@ export const APIKeyScopes: APIKeyScope[] = [
 	"boundary_usage:read",
 	"boundary_usage:update",
 	"chat:*",
+	"chat_automation:*",
+	"chat_automation:create",
+	"chat_automation:delete",
+	"chat_automation:read",
+	"chat_automation:update",
 	"chat:create",
 	"chat:delete",
 	"chat:read",
@@ -1200,6 +1210,13 @@ export interface Chat {
 	 * connect and disconnect.
 	 */
 	readonly has_unread: boolean;
+	/**
+	 * LastInjectedContext holds the most recently persisted
+	 * injected context parts (AGENTS.md files and skills). It
+	 * is updated only when context changes — first workspace
+	 * attach or agent change.
+	 */
+	readonly last_injected_context?: readonly ChatMessagePart[];
 }
 
 // From codersdk/chats.go
@@ -5578,6 +5595,7 @@ export type RBACResource =
 	| "audit_log"
 	| "boundary_usage"
 	| "chat"
+	| "chat_automation"
 	| "connection_log"
 	| "crypto_key"
 	| "debug_info"
@@ -5624,6 +5642,7 @@ export const RBACResources: RBACResource[] = [
 	"audit_log",
 	"boundary_usage",
 	"chat",
+	"chat_automation",
 	"connection_log",
 	"crypto_key",
 	"debug_info",
@@ -5918,56 +5937,62 @@ export interface Role {
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
+ */
+export const RoleAgentsAccess = "agents-access";
+
+// From codersdk/rbacroles.go
+/**
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleAuditor = "auditor";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleMember = "member";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationAdmin = "organization-admin";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationAuditor = "organization-auditor";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationMember = "organization-member";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationTemplateAdmin = "organization-template-admin";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationUserAdmin = "organization-user-admin";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOrganizationWorkspaceCreationBan =
 	"organization-workspace-creation-ban";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleOwner = "owner";
 
@@ -5986,13 +6011,13 @@ export interface RoleSyncSettings {
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleTemplateAdmin = "template-admin";
 
 // From codersdk/rbacroles.go
 /**
- * Ideally this roles would be generated from the rbac/roles.go package.
+ * Ideally these roles would be generated from the rbac/roles.go package.
  */
 export const RoleUserAdmin = "user-admin";
 

site/src/components/ActiveUserChart/ActiveUserChart.tsx

@@ -7,12 +7,12 @@ import {
 	ChartTooltipContent,
 } from "#/components/Chart/Chart";
 import {
-	HelpTooltip,
-	HelpTooltipContent,
-	HelpTooltipIconTrigger,
-	HelpTooltipText,
-	HelpTooltipTitle,
-} from "#/components/HelpTooltip/HelpTooltip";
+	HelpPopover,
+	HelpPopoverContent,
+	HelpPopoverIconTrigger,
+	HelpPopoverText,
+	HelpPopoverTitle,
+} from "#/components/HelpPopover/HelpPopover";
 import { formatDate } from "#/utils/time";
 
 const chartConfig = {
@@ -120,18 +120,18 @@ export const ActiveUsersTitle: FC<ActiveUsersTitleProps> = ({ interval }) => {
 	return (
 		<div className="flex items-center gap-2">
 			{interval === "day" ? "Daily" : "Weekly"} Active Users
-			<HelpTooltip>
-				<HelpTooltipIconTrigger size="small" />
-				<HelpTooltipContent>
-					<HelpTooltipTitle>How do we calculate active users?</HelpTooltipTitle>
-					<HelpTooltipText>
+			<HelpPopover>
+				<HelpPopoverIconTrigger size="small" />
+				<HelpPopoverContent>
+					<HelpPopoverTitle>How do we calculate active users?</HelpPopoverTitle>
+					<HelpPopoverText>
 						When a connection is initiated to a user&apos;s workspace they are
 						considered an active user. e.g. apps, web terminal, SSH. This is for
 						measuring user activity and has no connection to license
 						consumption.
-					</HelpTooltipText>
-				</HelpTooltipContent>
-			</HelpTooltip>
+					</HelpPopoverText>
+				</HelpPopoverContent>
+			</HelpPopover>
 		</div>
 	);
 };

site/src/components/Avatar/AvatarCard.tsx

@@ -37,7 +37,7 @@ export const AvatarCard: FC<AvatarCardProps> = ({
 			 *
 			 * @see {@link https://css-tricks.com/flexbox-truncated-text/}
 			 */}
-			<div css={{ marginRight: "auto", minWidth: 0 }}>
+			<div className="mr-auto min-w-0">
 				<h3
 					// Lets users hover over truncated text to see whole thing
 					title={header}

site/src/components/Badges/Badges.tsx

@@ -75,12 +75,7 @@ export const DeprecatedBadge: React.FC = () => {
 
 export const Badges: React.FC<React.PropsWithChildren> = ({ children }) => {
 	return (
-		<Stack
-			css={{ margin: "0 0 16px" }}
-			direction="row"
-			alignItems="center"
-			spacing={1}
-		>
+		<Stack className="mb-4" direction="row" alignItems="center" spacing={1}>
 			{children}
 		</Stack>
 	);

site/src/components/Calendar/Calendar.stories.tsx

@@ -6,6 +6,9 @@ import { Calendar } from "./Calendar";
 const meta: Meta<typeof Calendar> = {
 	title: "components/Calendar",
 	component: Calendar,
+	args: {
+		today: new Date("2025-03-15"),
+	},
 	decorators: [
 		(Story) => (
 			<div className="rounded-lg border border-solid border-border-default w-fit">
@@ -21,6 +24,7 @@ type Story = StoryObj<typeof Calendar>;
 export const Single: Story = {
 	args: {
 		mode: "single",
+		defaultMonth: new Date("2025-03-15"),
 		selected: new Date("2025-03-15"),
 	},
 };
@@ -34,6 +38,8 @@ export const Range: Story = {
 		return (
 			<Calendar
 				mode="range"
+				today={new Date("2025-03-15")}
+				defaultMonth={new Date("2025-03-10")}
 				selected={range}
 				onSelect={(r) => r && setRange(r)}
 				numberOfMonths={2}
@@ -45,6 +51,7 @@ export const Range: Story = {
 export const TwoMonths: Story = {
 	args: {
 		mode: "single",
+		defaultMonth: new Date("2025-03-15"),
 		numberOfMonths: 2,
 		selected: new Date("2025-03-15"),
 	},
@@ -53,6 +60,7 @@ export const TwoMonths: Story = {
 export const DisabledFutureDates: Story = {
 	args: {
 		mode: "single",
+		defaultMonth: new Date("2025-03-15"),
 		selected: new Date("2025-03-15"),
 		disabled: { after: new Date("2025-03-20") },
 	},

site/src/components/CustomLogo/CustomLogo.tsx

@@ -1,19 +1,18 @@
-import type { Interpolation, Theme } from "@emotion/react";
 import type { FC } from "react";
 import { CoderIcon } from "#/components/Icons/CoderIcon";
 import { getApplicationName, getLogoURL } from "#/utils/appearance";
+import { cn } from "#/utils/cn";
 
 /**
  * Enterprise customers can set a custom logo for their Coder application. Use
  * the custom logo wherever the Coder logo is used, if a custom one is provided.
  */
-export const CustomLogo: FC<{ css?: Interpolation<Theme> }> = (props) => {
+export const CustomLogo: FC<{ className?: string }> = ({ className }) => {
 	const applicationName = getApplicationName();
 	const logoURL = getLogoURL();
 
 	return logoURL ? (
 		<img
-			{...props}
 			alt={applicationName}
 			src={logoURL}
 			// This prevent browser to display the ugly error icon if the
@@ -24,10 +23,9 @@ export const CustomLogo: FC<{ css?: Interpolation<Theme> }> = (props) => {
 			onLoad={(e) => {
 				e.currentTarget.style.display = "inline";
 			}}
-			css={{ maxWidth: 200 }}
-			className="application-logo"
+			className={cn("max-w-[200px] application-logo", className)}
 		/>
 	) : (
-		<CoderIcon {...props} className="w-12 h-12" />
+		<CoderIcon className={cn("w-12 h-12", className)} />
 	);
 };

site/src/components/Dialogs/DeleteDialog/DeleteDialog.tsx

@@ -78,7 +78,7 @@ export const DeleteDialog: FC<DeleteDialogProps> = ({
 						<TextField
 							fullWidth
 							autoFocus
-							css={{ marginTop: 24 }}
+							className="mt-6"
 							name="confirmation"
 							autoComplete="off"
 							id={`${hookId}-confirm`}

site/src/components/DurationField/DurationField.tsx

@@ -77,12 +77,7 @@ export const DurationField: FC<DurationFieldProps> = (props) => {
 
 	return (
 		<div>
-			<div
-				css={{
-					display: "flex",
-					gap: 8,
-				}}
-			>
+			<div className="flex gap-2">
 				<TextField
 					{...textFieldProps}
 					fullWidth