exp: implement boundary logging telemetry

Add telemetry tracking for boundary feature usage:

- Add boundary_active_users and boundary_active_workspaces database tables
- Create BoundaryTelemetryCollector to collect usage in memory and flush to DB
- Record user/workspace/template IDs when boundary logs are received
- Include boundary active users/workspaces in telemetry snapshots
- Add cleanup of old boundary telemetry data (>24h) via dbpurge

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

@@ -4,7 +4,7 @@ description: |
 inputs:
   version:
     description: "The Go version to use."
-    default: "1.24.10"
+    default: "1.24.11"
   use-preinstalled-go:
     description: "Whether to use preinstalled Go."
     default: "false"

.golangci.yaml

@@ -211,14 +211,6 @@ issues:
     - path: scripts/rules.go
       linters:
         - ALL
-    # Boundary code is imported from github.com/coder/boundary and has different
-    # lint standards. Suppress lint issues in this imported code.
-    - path: enterprise/cli/boundary/
-      linters:
-        - revive
-        - gocritic
-        - gosec
-        - errorlint
 
   fix: true
   max-issues-per-linter: 0

Makefile

@@ -69,6 +69,9 @@ MOST_GO_SRC_FILES := $(shell \
 # All the shell files in the repo, excluding ignored files.
 SHELL_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.sh')
 
+MIGRATION_FILES := $(shell find ./coderd/database/migrations/ -maxdepth 1 $(FIND_EXCLUSIONS) -type f -name '*.sql')
+FIXTURE_FILES := $(shell find ./coderd/database/migrations/testdata/fixtures/ $(FIND_EXCLUSIONS) -type f -name '*.sql')
+
 # Ensure we don't use the user's git configs which might cause side-effects
 GIT_FLAGS = GIT_CONFIG_GLOBAL=/dev/null GIT_CONFIG_SYSTEM=/dev/null
 
@@ -561,7 +564,7 @@ endif
 
 # Note: we don't run zizmor in the lint target because it takes a while. CI
 #       runs it explicitly.
-lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/actions/actionlint lint/check-scopes
+lint: lint/shellcheck lint/go lint/ts lint/examples lint/helm lint/site-icons lint/markdown lint/actions/actionlint lint/check-scopes lint/migrations
 .PHONY: lint
 
 lint/site-icons:
@@ -619,6 +622,12 @@ lint/check-scopes: coderd/database/dump.sql
 	go run ./scripts/check-scopes
 .PHONY: lint/check-scopes
 
+# Verify migrations do not hardcode the public schema.
+lint/migrations:
+	./scripts/check_pg_schema.sh "Migrations" $(MIGRATION_FILES)
+	./scripts/check_pg_schema.sh "Fixtures" $(FIXTURE_FILES)
+.PHONY: lint/migrations
+
 # All files generated by the database should be added here, and this can be used
 # as a target for jobs that need to run after the database is generated.
 DB_GEN_FILES := \

agent/agent.go

@@ -40,6 +40,7 @@ import (
 	"github.com/coder/clistat"
 	"github.com/coder/coder/v2/agent/agentcontainers"
 	"github.com/coder/coder/v2/agent/agentexec"
+	"github.com/coder/coder/v2/agent/agentfiles"
 	"github.com/coder/coder/v2/agent/agentscripts"
 	"github.com/coder/coder/v2/agent/agentsocket"
 	"github.com/coder/coder/v2/agent/agentssh"
@@ -295,6 +296,8 @@ type agent struct {
 	containerAPIOptions []agentcontainers.Option
 	containerAPI        *agentcontainers.API
 
+	filesAPI *agentfiles.API
+
 	socketServerEnabled bool
 	socketPath          string
 	socketServer        *agentsocket.Server
@@ -365,6 +368,8 @@ func (a *agent) init() {
 
 	a.containerAPI = agentcontainers.NewAPI(a.logger.Named("containers"), containerAPIOpts...)
 
+	a.filesAPI = agentfiles.NewAPI(a.logger.Named("files"), a.filesystem)
+
 	a.reconnectingPTYServer = reconnectingpty.NewServer(
 		a.logger.Named("reconnecting-pty"),
 		a.sshServer,

agent/agentfiles/api.go

@@ -0,0 +1,36 @@
+package agentfiles
+
+import (
+	"net/http"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/spf13/afero"
+
+	"cdr.dev/slog/v3"
+)
+
+// API exposes file-related operations performed through the agent.
+type API struct {
+	logger     slog.Logger
+	filesystem afero.Fs
+}
+
+func NewAPI(logger slog.Logger, filesystem afero.Fs) *API {
+	api := &API{
+		logger:     logger,
+		filesystem: filesystem,
+	}
+	return api
+}
+
+// Routes returns the HTTP handler for file-related routes.
+func (api *API) Routes() http.Handler {
+	r := chi.NewRouter()
+
+	r.Post("/list-directory", api.HandleLS)
+	r.Get("/read-file", api.HandleReadFile)
+	r.Post("/write-file", api.HandleWriteFile)
+	r.Post("/edit-files", api.HandleEditFiles)
+
+	return r
+}

agent/agentfiles/files.go

@@ -1,4 +1,4 @@
-package agent
+package agentfiles
 
 import (
 	"context"
@@ -25,7 +25,7 @@ import (
 
 type HTTPResponseCode = int
 
-func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 
 	query := r.URL.Query()
@@ -42,7 +42,7 @@ func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	status, err := a.streamFile(ctx, rw, path, offset, limit)
+	status, err := api.streamFile(ctx, rw, path, offset, limit)
 	if err != nil {
 		httpapi.Write(ctx, rw, status, codersdk.Response{
 			Message: err.Error(),
@@ -51,12 +51,12 @@ func (a *agent) HandleReadFile(rw http.ResponseWriter, r *http.Request) {
 	}
 }
 
-func (a *agent) streamFile(ctx context.Context, rw http.ResponseWriter, path string, offset, limit int64) (HTTPResponseCode, error) {
+func (api *API) streamFile(ctx context.Context, rw http.ResponseWriter, path string, offset, limit int64) (HTTPResponseCode, error) {
 	if !filepath.IsAbs(path) {
 		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
 	}
 
-	f, err := a.filesystem.Open(path)
+	f, err := api.filesystem.Open(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -97,13 +97,13 @@ func (a *agent) streamFile(ctx context.Context, rw http.ResponseWriter, path str
 	reader := io.NewSectionReader(f, offset, bytesToRead)
 	_, err = io.Copy(rw, reader)
 	if err != nil && !errors.Is(err, io.EOF) && ctx.Err() == nil {
-		a.logger.Error(ctx, "workspace agent read file", slog.Error(err))
+		api.logger.Error(ctx, "workspace agent read file", slog.Error(err))
 	}
 
 	return 0, nil
 }
 
-func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 
 	query := r.URL.Query()
@@ -118,7 +118,7 @@ func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	status, err := a.writeFile(ctx, r, path)
+	status, err := api.writeFile(ctx, r, path)
 	if err != nil {
 		httpapi.Write(ctx, rw, status, codersdk.Response{
 			Message: err.Error(),
@@ -131,13 +131,13 @@ func (a *agent) HandleWriteFile(rw http.ResponseWriter, r *http.Request) {
 	})
 }
 
-func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HTTPResponseCode, error) {
+func (api *API) writeFile(ctx context.Context, r *http.Request, path string) (HTTPResponseCode, error) {
 	if !filepath.IsAbs(path) {
 		return http.StatusBadRequest, xerrors.Errorf("file path must be absolute: %q", path)
 	}
 
 	dir := filepath.Dir(path)
-	err := a.filesystem.MkdirAll(dir, 0o755)
+	err := api.filesystem.MkdirAll(dir, 0o755)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -149,7 +149,7 @@ func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HT
 		return status, err
 	}
 
-	f, err := a.filesystem.Create(path)
+	f, err := api.filesystem.Create(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -164,13 +164,13 @@ func (a *agent) writeFile(ctx context.Context, r *http.Request, path string) (HT
 
 	_, err = io.Copy(f, r.Body)
 	if err != nil && !errors.Is(err, io.EOF) && ctx.Err() == nil {
-		a.logger.Error(ctx, "workspace agent write file", slog.Error(err))
+		api.logger.Error(ctx, "workspace agent write file", slog.Error(err))
 	}
 
 	return 0, nil
 }
 
-func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 
 	var req workspacesdk.FileEditRequest
@@ -188,7 +188,7 @@ func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	var combinedErr error
 	status := http.StatusOK
 	for _, edit := range req.Files {
-		s, err := a.editFile(r.Context(), edit.Path, edit.Edits)
+		s, err := api.editFile(r.Context(), edit.Path, edit.Edits)
 		// Keep the highest response status, so 500 will be preferred over 400, etc.
 		if s > status {
 			status = s
@@ -210,7 +210,7 @@ func (a *agent) HandleEditFiles(rw http.ResponseWriter, r *http.Request) {
 	})
 }
 
-func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.FileEdit) (int, error) {
+func (api *API) editFile(ctx context.Context, path string, edits []workspacesdk.FileEdit) (int, error) {
 	if path == "" {
 		return http.StatusBadRequest, xerrors.New("\"path\" is required")
 	}
@@ -223,7 +223,7 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 		return http.StatusBadRequest, xerrors.New("must specify at least one edit")
 	}
 
-	f, err := a.filesystem.Open(path)
+	f, err := api.filesystem.Open(path)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {
@@ -252,7 +252,7 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 
 	// Create an adjacent file to ensure it will be on the same device and can be
 	// moved atomically.
-	tmpfile, err := afero.TempFile(a.filesystem, filepath.Dir(path), filepath.Base(path))
+	tmpfile, err := afero.TempFile(api.filesystem, filepath.Dir(path), filepath.Base(path))
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}
@@ -260,13 +260,13 @@ func (a *agent) editFile(ctx context.Context, path string, edits []workspacesdk.
 
 	_, err = io.Copy(tmpfile, replace.Chain(f, transforms...))
 	if err != nil {
-		if rerr := a.filesystem.Remove(tmpfile.Name()); rerr != nil {
-			a.logger.Warn(ctx, "unable to clean up temp file", slog.Error(rerr))
+		if rerr := api.filesystem.Remove(tmpfile.Name()); rerr != nil {
+			api.logger.Warn(ctx, "unable to clean up temp file", slog.Error(rerr))
 		}
 		return http.StatusInternalServerError, xerrors.Errorf("edit %s: %w", path, err)
 	}
 
-	err = a.filesystem.Rename(tmpfile.Name(), path)
+	err = api.filesystem.Rename(tmpfile.Name(), path)
 	if err != nil {
 		return http.StatusInternalServerError, err
 	}

agent/agentfiles/files_test.go

@@ -1,11 +1,13 @@
-package agent_test
+package agentfiles_test
 
 import (
 	"bytes"
 	"context"
+	"encoding/json"
 	"fmt"
 	"io"
 	"net/http"
+	"net/http/httptest"
 	"os"
 	"path/filepath"
 	"runtime"
@@ -16,10 +18,10 @@ import (
 	"github.com/stretchr/testify/require"
 	"golang.org/x/xerrors"
 
-	"github.com/coder/coder/v2/agent"
-	"github.com/coder/coder/v2/agent/agenttest"
-	"github.com/coder/coder/v2/coderd/coderdtest"
-	"github.com/coder/coder/v2/codersdk/agentsdk"
+	"cdr.dev/slog/v3"
+	"cdr.dev/slog/v3/sloggers/slogtest"
+	"github.com/coder/coder/v2/agent/agentfiles"
+	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/workspacesdk"
 	"github.com/coder/coder/v2/testutil"
 )
@@ -106,15 +108,15 @@ func TestReadFile(t *testing.T) {
 
 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath {
-				return os.ErrPermission
-			}
-			return nil
-		})
+
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath {
+			return os.ErrPermission
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)
 
 	dirPath := filepath.Join(tmpdir, "a-directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -260,19 +262,22 @@ func TestReadFile(t *testing.T) {
 			ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
 			defer cancel()
 
-			reader, mimeType, err := conn.ReadFile(ctx, tt.path, tt.offset, tt.limit)
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodGet, fmt.Sprintf("/read-file?path=%s&offset=%d&limit=%d", tt.path, tt.offset, tt.limit), nil)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				require.Contains(t, cerr.Error(), tt.error)
-				require.Equal(t, tt.errCode, cerr.StatusCode())
-			} else {
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
 				require.NoError(t, err)
-				defer reader.Close()
-				bytes, err := io.ReadAll(reader)
+				require.ErrorContains(t, got, tt.error)
+				require.Equal(t, tt.errCode, w.Code)
+			} else {
+				bytes, err := io.ReadAll(w.Body)
 				require.NoError(t, err)
 				require.Equal(t, tt.bytes, bytes)
-				require.Equal(t, tt.mimeType, mimeType)
+				require.Equal(t, tt.mimeType, w.Header().Get("Content-Type"))
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 		})
 	}
@@ -284,15 +289,14 @@ func TestWriteFile(t *testing.T) {
 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms-file")
 	noPermsDirPath := filepath.Join(tmpdir, "no-perms-dir")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath || file == noPermsDirPath {
-				return os.ErrPermission
-			}
-			return nil
-		})
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath || file == noPermsDirPath {
+			return os.ErrPermission
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)
 
 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -371,17 +375,21 @@ func TestWriteFile(t *testing.T) {
 			defer cancel()
 
 			reader := bytes.NewReader(tt.bytes)
-			err := conn.WriteFile(ctx, tt.path, reader)
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodPost, fmt.Sprintf("/write-file?path=%s", tt.path), reader)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				require.Contains(t, cerr.Error(), tt.error)
-				require.Equal(t, tt.errCode, cerr.StatusCode())
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
+				require.NoError(t, err)
+				require.ErrorContains(t, got, tt.error)
+				require.Equal(t, tt.errCode, w.Code)
 			} else {
+				bytes, err := afero.ReadFile(fs, tt.path)
 				require.NoError(t, err)
-				b, err := afero.ReadFile(fs, tt.path)
-				require.NoError(t, err)
-				require.Equal(t, tt.bytes, b)
+				require.Equal(t, tt.bytes, bytes)
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 		})
 	}
@@ -393,21 +401,20 @@ func TestEditFiles(t *testing.T) {
 	tmpdir := os.TempDir()
 	noPermsFilePath := filepath.Join(tmpdir, "no-perms-file")
 	failRenameFilePath := filepath.Join(tmpdir, "fail-rename")
-	//nolint:dogsled
-	conn, _, _, fs, _ := setupAgent(t, agentsdk.Manifest{}, 0, func(_ *agenttest.Client, opts *agent.Options) {
-		opts.Filesystem = newTestFs(opts.Filesystem, func(call, file string) error {
-			if file == noPermsFilePath {
-				return &os.PathError{
-					Op:   call,
-					Path: file,
-					Err:  os.ErrPermission,
-				}
-			} else if file == failRenameFilePath && call == "rename" {
-				return xerrors.New("rename failed")
+	logger := slogtest.Make(t, &slogtest.Options{IgnoreErrors: true}).Leveled(slog.LevelDebug)
+	fs := newTestFs(afero.NewMemMapFs(), func(call, file string) error {
+		if file == noPermsFilePath {
+			return &os.PathError{
+				Op:   call,
+				Path: file,
+				Err:  os.ErrPermission,
 			}
-			return nil
-		})
+		} else if file == failRenameFilePath && call == "rename" {
+			return xerrors.New("rename failed")
+		}
+		return nil
 	})
+	api := agentfiles.NewAPI(logger, fs)
 
 	dirPath := filepath.Join(tmpdir, "directory")
 	err := fs.MkdirAll(dirPath, 0o755)
@@ -701,16 +708,26 @@ func TestEditFiles(t *testing.T) {
 				require.NoError(t, err)
 			}
 
-			err := conn.EditFiles(ctx, workspacesdk.FileEditRequest{Files: tt.edits})
+			buf := bytes.NewBuffer(nil)
+			enc := json.NewEncoder(buf)
+			enc.SetEscapeHTML(false)
+			err := enc.Encode(workspacesdk.FileEditRequest{Files: tt.edits})
+			require.NoError(t, err)
+
+			w := httptest.NewRecorder()
+			r := httptest.NewRequestWithContext(ctx, http.MethodPost, "/edit-files", buf)
+			api.Routes().ServeHTTP(w, r)
+
 			if tt.errCode != 0 {
-				require.Error(t, err)
-				cerr := coderdtest.SDKError(t, err)
-				for _, error := range tt.errors {
-					require.Contains(t, cerr.Error(), error)
-				}
-				require.Equal(t, tt.errCode, cerr.StatusCode())
-			} else {
+				got := &codersdk.Error{}
+				err := json.NewDecoder(w.Body).Decode(got)
 				require.NoError(t, err)
+				for _, error := range tt.errors {
+					require.ErrorContains(t, got, error)
+				}
+				require.Equal(t, tt.errCode, w.Code)
+			} else {
+				require.Equal(t, http.StatusOK, w.Code)
 			}
 			for path, expect := range tt.expected {
 				b, err := afero.ReadFile(fs, path)

agent/agentfiles/ls.go

@@ -1,4 +1,4 @@
-package agent
+package agentfiles
 
 import (
 	"errors"
@@ -21,7 +21,7 @@ import (
 
 var WindowsDriveRegex = regexp.MustCompile(`^[a-zA-Z]:\\$`)
 
-func (a *agent) HandleLS(rw http.ResponseWriter, r *http.Request) {
+func (api *API) HandleLS(rw http.ResponseWriter, r *http.Request) {
 	ctx := r.Context()
 
 	// An absolute path may be optionally provided, otherwise a path split into an
@@ -43,7 +43,7 @@ func (a *agent) HandleLS(rw http.ResponseWriter, r *http.Request) {
 		return
 	}
 
-	resp, err := listFiles(a.filesystem, path, req)
+	resp, err := listFiles(api.filesystem, path, req)
 	if err != nil {
 		status := http.StatusInternalServerError
 		switch {

agent/agentfiles/ls_internal_test.go

@@ -1,4 +1,4 @@
-package agent
+package agentfiles
 
 import (
 	"os"

agent/api.go

@@ -27,6 +27,8 @@ func (a *agent) apiHandler() http.Handler {
 		})
 	})
 
+	r.Mount("/api/v0", a.filesAPI.Routes())
+
 	if a.devcontainers {
 		r.Mount("/api/v0/containers", a.containerAPI.Routes())
 	} else if manifest := a.manifest.Load(); manifest != nil && manifest.ParentID != uuid.Nil {
@@ -49,10 +51,6 @@ func (a *agent) apiHandler() http.Handler {
 
 	r.Get("/api/v0/listening-ports", a.listeningPortsHandler.handler)
 	r.Get("/api/v0/netcheck", a.HandleNetcheck)
-	r.Post("/api/v0/list-directory", a.HandleLS)
-	r.Get("/api/v0/read-file", a.HandleReadFile)
-	r.Post("/api/v0/write-file", a.HandleWriteFile)
-	r.Post("/api/v0/edit-files", a.HandleEditFiles)
 	r.Get("/debug/logs", a.HandleHTTPDebugLogs)
 	r.Get("/debug/magicsock", a.HandleHTTPDebugMagicsock)
 	r.Get("/debug/magicsock/debug-logging/{state}", a.HandleHTTPMagicsockDebugLoggingState)

cli/cliui/parameter.go

@@ -10,12 +10,8 @@ import (
 	"github.com/coder/serpent"
 )
 
-func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.TemplateVersionParameter, defaultOverrides map[string]string) (string, error) {
-	label := templateVersionParameter.Name
-	if templateVersionParameter.DisplayName != "" {
-		label = templateVersionParameter.DisplayName
-	}
-
+func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.TemplateVersionParameter, name, defaultValue string) (string, error) {
+	label := name
 	if templateVersionParameter.Ephemeral {
 		label += pretty.Sprint(DefaultStyles.Warn, " (build option)")
 	}
@@ -26,11 +22,6 @@ func RichParameter(inv *serpent.Invocation, templateVersionParameter codersdk.Te
 		_, _ = fmt.Fprintln(inv.Stdout, "  "+strings.TrimSpace(strings.Join(strings.Split(templateVersionParameter.DescriptionPlaintext, "\n"), "\n  "))+"\n")
 	}
 
-	defaultValue := templateVersionParameter.DefaultValue
-	if v, ok := defaultOverrides[templateVersionParameter.Name]; ok {
-		defaultValue = v
-	}
-
 	var err error
 	var value string
 	switch {

cli/cliui/prompt.go

@@ -32,12 +32,12 @@ type PromptOptions struct {
 const skipPromptFlag = "yes"
 
 // SkipPromptOption adds a "--yes/-y" flag to the cmd that can be used to skip
-// prompts.
+// confirmation prompts.
 func SkipPromptOption() serpent.Option {
 	return serpent.Option{
 		Flag:          skipPromptFlag,
 		FlagShorthand: "y",
-		Description:   "Bypass prompts.",
+		Description:   "Bypass confirmation prompts.",
 		// Discard
 		Value: serpent.BoolOf(new(bool)),
 	}

cli/create.go

@@ -42,9 +42,10 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 		stopAfter       time.Duration
 		workspaceName   string
 
-		parameterFlags     workspaceParameterFlags
-		autoUpdates        string
-		copyParametersFrom string
+		parameterFlags       workspaceParameterFlags
+		autoUpdates          string
+		copyParametersFrom   string
+		useParameterDefaults bool
 		// Organization context is only required if more than 1 template
 		// shares the same name across multiple organizations.
 		orgContext = NewOrganizationContext()
@@ -308,7 +309,7 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 				displayAppliedPreset(inv, preset, presetParameters)
 			} else {
 				// Inform the user that no preset was applied
-				_, _ = fmt.Fprintf(inv.Stdout, "%s", cliui.Bold("No preset applied."))
+				_, _ = fmt.Fprintf(inv.Stdout, "%s\n", cliui.Bold("No preset applied."))
 			}
 
 			if opts.BeforeCreate != nil {
@@ -329,6 +330,8 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 				RichParameterDefaults: cliBuildParameterDefaults,
 
 				SourceWorkspaceParameters: sourceWorkspaceParameters,
+
+				UseParameterDefaults: useParameterDefaults,
 			})
 			if err != nil {
 				return xerrors.Errorf("prepare build: %w", err)
@@ -435,6 +438,12 @@ func (r *RootCmd) Create(opts CreateOptions) *serpent.Command {
 			Description: "Specify the source workspace name to copy parameters from.",
 			Value:       serpent.StringOf(&copyParametersFrom),
 		},
+		serpent.Option{
+			Flag:        "use-parameter-defaults",
+			Env:         "CODER_WORKSPACE_USE_PARAMETER_DEFAULTS",
+			Description: "Automatically accept parameter defaults when no value is provided.",
+			Value:       serpent.BoolOf(&useParameterDefaults),
+		},
 		cliui.SkipPromptOption(),
 	)
 	cmd.Options = append(cmd.Options, parameterFlags.cliParameters()...)
@@ -459,6 +468,8 @@ type prepWorkspaceBuildArgs struct {
 	RichParameters        []codersdk.WorkspaceBuildParameter
 	RichParameterFile     string
 	RichParameterDefaults []codersdk.WorkspaceBuildParameter
+
+	UseParameterDefaults bool
 }
 
 // resolvePreset returns the preset matching the given presetName (if specified),
@@ -561,7 +572,8 @@ func prepWorkspaceBuild(inv *serpent.Invocation, client *codersdk.Client, args p
 		WithPromptRichParameters(args.PromptRichParameters).
 		WithRichParameters(args.RichParameters).
 		WithRichParametersFile(parameterFile).
-		WithRichParametersDefaults(args.RichParameterDefaults)
+		WithRichParametersDefaults(args.RichParameterDefaults).
+		WithUseParameterDefaults(args.UseParameterDefaults)
 	buildParameters, err := resolver.Resolve(inv, args.Action, templateVersionParameters)
 	if err != nil {
 		return nil, err

cli/create_test.go

@@ -318,353 +318,437 @@ func prepareEchoResponses(parameters []*proto.RichParameter, presets ...*proto.P
 	}
 }
 
+type param struct {
+	name    string
+	ptype   string
+	value   string
+	mutable bool
+}
+
 func TestCreateWithRichParameters(t *testing.T) {
 	t.Parallel()
 
-	const (
-		firstParameterName        = "first_parameter"
-		firstParameterDescription = "This is first parameter"
-		firstParameterValue       = "1"
-
-		secondParameterName        = "second_parameter"
-		secondParameterDisplayName = "Second Parameter"
-		secondParameterDescription = "This is second parameter"
-		secondParameterValue       = "2"
-
-		immutableParameterName        = "third_parameter"
-		immutableParameterDescription = "This is not mutable parameter"
-		immutableParameterValue       = "4"
-	)
-
-	echoResponses := func() *echo.Responses {
-		return prepareEchoResponses([]*proto.RichParameter{
-			{Name: firstParameterName, Description: firstParameterDescription, Mutable: true},
-			{Name: secondParameterName, DisplayName: secondParameterDisplayName, Description: secondParameterDescription, Mutable: true},
-			{Name: immutableParameterName, Description: immutableParameterDescription, Mutable: false},
-		})
+	// Default parameters and their expected values.
+	params := []param{
+		{
+			name:    "number_param",
+			ptype:   "number",
+			value:   "777",
+			mutable: true,
+		},
+		{
+			name:    "string_param",
+			ptype:   "string",
+			value:   "qux",
+			mutable: true,
+		},
+		{
+			name: "bool_param",
+			// TODO: Setting the type breaks booleans.  It claims the default is false
+			// but when you then accept this default it errors saying that the value
+			// must be true or false.  For now, use a string.
+			ptype:   "string",
+			value:   "false",
+			mutable: true,
+		},
+		{
+			name:    "immutable_string_param",
+			ptype:   "string",
+			value:   "i am eternal",
+			mutable: false,
+		},
 	}
 
-	t.Run("InputParameters", func(t *testing.T) {
-		t.Parallel()
+	type testContext struct {
+		client        *codersdk.Client
+		member        *codersdk.Client
+		owner         codersdk.CreateFirstUserResponse
+		template      codersdk.Template
+		workspaceName string
+	}
 
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+	tests := []struct {
+		name string
+		// setup runs before the command is started and return arguments that will
+		// be appended to the create command.
+		setup func() []string
+		// handlePty optionally runs after the command is started.  It should handle
+		// all expected prompts from the pty.
+		handlePty func(pty *ptytest.PTY)
+		// postRun runs after the command has finished but before the workspace is
+		// verified.  It must return the workspace name to check (used for the copy
+		// workspace tests).
+		postRun func(t *testing.T, args testContext) string
+		// errors contains expected errors.  The workspace will not be verified if
+		// errors are expected.
+		errors []string
+		// inputParameters overrides the default parameters.
+		inputParameters []param
+		// expectedParameters defaults to inputParameters.
+		expectedParameters []param
+		// withDefaults sets DefaultValue to each parameter's value.
+		withDefaults bool
+	}{
+		{
+			name: "ValuesFromPrompt",
+			handlePty: func(pty *ptytest.PTY) {
+				// Enter the value for each parameter as prompted.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.WriteLine(param.value)
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromDefaultFlags",
+			setup: func() []string {
+				// Provide the defaults on the command line.
+				args := []string{}
+				for _, param := range params {
+					args = append(args, "--parameter-default", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Simply accept the defaults.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.ExpectMatch(`Enter a value (default: "` + param.value + `")`)
+					pty.WriteLine("")
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromFile",
+			setup: func() []string {
+				// Create a file with the values.
+				tempDir := t.TempDir()
+				removeTmpDirUntilSuccessAfterTest(t, tempDir)
+				parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
+				for _, param := range params {
+					_, err := parameterFile.WriteString(fmt.Sprintf("%s: %s\n", param.name, param.value))
+					require.NoError(t, err)
+				}
 
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
+				return []string{"--rich-parameter-file", parameterFile.Name()}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "ValuesFromFlags",
+			setup: func() []string {
+				// Provide the values on the command line.
+				var args []string
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			name: "MisspelledParameter",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{}
+				for i, param := range params {
+					if i == 0 {
+						// Slightly misspell the first parameter with an extra character.
+						args = append(args, "--parameter", fmt.Sprintf("n%s=%s", param.name, param.value))
+					} else {
+						args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+					}
+				}
+				return args
+			},
+			errors: []string{
+				"parameter \"n" + params[0].name + "\" is not present in the template",
+				"Did you mean: " + params[0].name,
+			},
+		},
+		{
+			name: "ValuesFromWorkspace",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{"-y"}
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			postRun: func(t *testing.T, tctx testContext) string {
+				inv, root := clitest.New(t, "create", "--copy-parameters-from", tctx.workspaceName, "other-workspace", "-y")
+				clitest.SetupConfig(t, tctx.member, root)
+				pty := ptytest.New(t).Attach(inv)
+				inv.Stdout = pty.Output()
+				inv.Stderr = pty.Output()
+				err := inv.Run()
+				require.NoError(t, err, "failed to create a workspace based on the source workspace")
+				return "other-workspace"
+			},
+		},
+		{
+			name: "ValuesFromOutdatedWorkspace",
+			setup: func() []string {
+				// Provide the values on the command line.
+				args := []string{"-y"}
+				for _, param := range params {
+					args = append(args, "--parameter", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			postRun: func(t *testing.T, tctx testContext) string {
+				// Update the template to a new version.
+				version2 := coderdtest.CreateTemplateVersion(t, tctx.client, tctx.owner.OrganizationID, prepareEchoResponses([]*proto.RichParameter{
+					{Name: "another_parameter", Type: "string", DefaultValue: "not-relevant"},
+				}), func(ctvr *codersdk.CreateTemplateVersionRequest) {
+					ctvr.TemplateID = tctx.template.ID
+				})
+				coderdtest.AwaitTemplateVersionJobCompleted(t, tctx.client, version2.ID)
+				coderdtest.UpdateActiveTemplateVersion(t, tctx.client, tctx.template.ID, version2.ID)
 
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name)
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
+				// Then create the copy.  It should use the old template version.
+				inv, root := clitest.New(t, "create", "--copy-parameters-from", tctx.workspaceName, "other-workspace", "-y")
+				clitest.SetupConfig(t, tctx.member, root)
+				pty := ptytest.New(t).Attach(inv)
+				inv.Stdout = pty.Output()
+				inv.Stderr = pty.Output()
+				err := inv.Run()
+				require.NoError(t, err, "failed to create a workspace based on the source workspace")
+				return "other-workspace"
+			},
+		},
+		{
+			name: "ValuesFromTemplateDefaults",
+			handlePty: func(pty *ptytest.PTY) {
+				// Simply accept the defaults.
+				for _, param := range params {
+					pty.ExpectMatch(param.name)
+					pty.ExpectMatch(`Enter a value (default: "` + param.value + `")`)
+					pty.WriteLine("")
+				}
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+		},
+		{
+			name: "ValuesFromTemplateDefaultsNoPrompt",
+			setup: func() []string {
+				return []string{"--use-parameter-defaults"}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Default values should get printed.
+				for _, param := range params {
+					pty.ExpectMatch(fmt.Sprintf("%s: '%s'", param.name, param.value))
+				}
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+		},
+		{
+			name: "ValuesFromDefaultFlagsNoPrompt",
+			setup: func() []string {
+				// Provide the defaults on the command line.
+				args := []string{"--use-parameter-defaults"}
+				for _, param := range params {
+					args = append(args, "--parameter-default", fmt.Sprintf("%s=%s", param.name, param.value))
+				}
+				return args
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Default values should get printed.
+				for _, param := range params {
+					pty.ExpectMatch(fmt.Sprintf("%s: '%s'", param.name, param.value))
+				}
+				// No prompts, we only need to confirm.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+		},
+		{
+			// File and flags should override template defaults.  Additionally, if a
+			// value has no default value we should still get a prompt for it.
+			name: "ValuesFromMultipleSources",
+			setup: func() []string {
+				tempDir := t.TempDir()
+				removeTmpDirUntilSuccessAfterTest(t, tempDir)
+				parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
+				_, err := parameterFile.WriteString(`
+file_param: from file
+cli_param: from file`)
+				require.NoError(t, err)
+				return []string{
+					"--use-parameter-defaults",
+					"--rich-parameter-file", parameterFile.Name(),
+					"--parameter-default", "file_param=from cli default",
+					"--parameter-default", "cli_param=from cli default",
+					"--parameter", "cli_param=from cli",
+				}
+			},
+			handlePty: func(pty *ptytest.PTY) {
+				// Should get prompted for the input param since it has no default.
+				pty.ExpectMatch("input_param")
+				pty.WriteLine("from input")
 
-		matches := []string{
-			firstParameterDescription, firstParameterValue,
-			secondParameterDisplayName, "",
-			secondParameterDescription, secondParameterValue,
-			immutableParameterDescription, immutableParameterValue,
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
+				// Confirm the creation.
+				pty.ExpectMatch("Confirm create?")
+				pty.WriteLine("yes")
+			},
+			withDefaults: true,
+			inputParameters: []param{
+				{
+					name:  "template_param",
+					value: "from template default",
+				},
+				{
+					name:  "file_param",
+					value: "from template default",
+				},
+				{
+					name:  "cli_param",
+					value: "from template default",
+				},
+				{
+					name: "input_param",
+				},
+			},
+			expectedParameters: []param{
+				{
+					name:  "template_param",
+					value: "from template default",
+				},
+				{
+					name:  "file_param",
+					value: "from file",
+				},
+				{
+					name:  "cli_param",
+					value: "from cli",
+				},
+				{
+					name:  "input_param",
+					value: "from input",
+				},
+			},
+		},
+	}
 
-			if value != "" {
-				pty.WriteLine(value)
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			parameters := params
+			if len(tt.inputParameters) > 0 {
+				parameters = tt.inputParameters
 			}
-		}
-		<-doneChan
-	})
 
-	t.Run("ParametersDefaults", func(t *testing.T) {
-		t.Parallel()
+			// Convert parameters for the echo provisioner response.
+			var rparams []*proto.RichParameter
+			for i, param := range parameters {
+				defaultValue := ""
+				if tt.withDefaults {
+					defaultValue = param.value
+				}
+				rparams = append(rparams, &proto.RichParameter{
+					Name:         param.name,
+					Type:         param.ptype,
+					Mutable:      param.mutable,
+					DefaultValue: defaultValue,
+					Order:        int32(i), //nolint:gosec
+				})
+			}
 
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+			// Set up the template.
+			client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
+			owner := coderdtest.CreateFirstUser(t, client)
+			member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
+			version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, prepareEchoResponses(rparams))
 
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
+			coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
+			template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
 
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter-default", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter-default", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter-default", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
+			// Run the command, possibly setting up values.
+			workspaceName := "my-workspace"
+			args := []string{"create", workspaceName, "--template", template.Name}
+			if tt.setup != nil {
+				args = append(args, tt.setup()...)
+			}
+			inv, root := clitest.New(t, args...)
+			clitest.SetupConfig(t, member, root)
+			doneChan := make(chan error)
+			pty := ptytest.New(t).Attach(inv)
+			go func() {
+				doneChan <- inv.Run()
+			}()
 
-		matches := []string{
-			firstParameterDescription, firstParameterValue,
-			secondParameterDescription, secondParameterValue,
-			immutableParameterDescription, immutableParameterValue,
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			defaultValue := matches[i+1]
+			// The test may do something with the pty.
+			if tt.handlePty != nil {
+				tt.handlePty(pty)
+			}
 
-			pty.ExpectMatch(match)
-			pty.ExpectMatch(`Enter a value (default: "` + defaultValue + `")`)
-			pty.WriteLine("")
-		}
-		pty.ExpectMatch("Confirm create?")
-		pty.WriteLine("yes")
-		<-doneChan
+			// Wait for the command to exit.
+			err := <-doneChan
 
-		// Verify that the expected default values were used.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
+			// The test may want to run additional setup like copying the workspace.
+			if tt.postRun != nil {
+				workspaceName = tt.postRun(t, testContext{
+					client:        client,
+					member:        member,
+					owner:         owner,
+					template:      template,
+					workspaceName: workspaceName,
+				})
+			}
 
-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: "my-workspace",
+			if len(tt.errors) > 0 {
+				require.Error(t, err)
+				for _, errstr := range tt.errors {
+					assert.ErrorContains(t, err, errstr)
+				}
+			} else {
+				require.NoError(t, err)
+
+				// Verify the workspace was created and has the right template and values.
+				ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
+				defer cancel()
+
+				workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{Name: workspaceName})
+				require.NoError(t, err, "expected to find created workspace")
+				require.Len(t, workspaces.Workspaces, 1)
+
+				workspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
+				require.Equal(t, version.ID, workspaceLatestBuild.TemplateVersionID)
+
+				buildParameters, err := client.WorkspaceBuildParameters(ctx, workspaceLatestBuild.ID)
+				require.NoError(t, err)
+				if len(tt.expectedParameters) > 0 {
+					parameters = tt.expectedParameters
+				}
+				require.Len(t, buildParameters, len(parameters))
+				for _, param := range parameters {
+					require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: param.name, Value: param.value})
+				}
+			}
 		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		workspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-		require.Equal(t, version.ID, workspaceLatestBuild.TemplateVersionID)
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, workspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
-
-	t.Run("RichParametersFile", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		tempDir := t.TempDir()
-		removeTmpDirUntilSuccessAfterTest(t, tempDir)
-		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
-		_, _ = parameterFile.WriteString(
-			firstParameterName + ": " + firstParameterValue + "\n" +
-				secondParameterName + ": " + secondParameterValue + "\n" +
-				immutableParameterName + ": " + immutableParameterValue)
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "--rich-parameter-file", parameterFile.Name())
-		clitest.SetupConfig(t, member, root)
-
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
-
-		matches := []string{
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
-			pty.WriteLine(value)
-		}
-		<-doneChan
-	})
-
-	t.Run("ParameterFlags", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		doneChan := make(chan struct{})
-		pty := ptytest.New(t).Attach(inv)
-		go func() {
-			defer close(doneChan)
-			err := inv.Run()
-			assert.NoError(t, err)
-		}()
-
-		matches := []string{
-			"Confirm create?", "yes",
-		}
-		for i := 0; i < len(matches); i += 2 {
-			match := matches[i]
-			value := matches[i+1]
-			pty.ExpectMatch(match)
-			pty.WriteLine(value)
-		}
-		<-doneChan
-	})
-
-	t.Run("WrongParameterName/DidYouMean", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		wrongFirstParameterName := "frst-prameter"
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name,
-			"--parameter", fmt.Sprintf("%s=%s", wrongFirstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		assert.ErrorContains(t, err, "parameter \""+wrongFirstParameterName+"\" is not present in the template")
-		assert.ErrorContains(t, err, "Did you mean: "+firstParameterName)
-	})
-
-	t.Run("CopyParameters", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		// Firstly, create a regular workspace using template with parameters.
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "-y",
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		require.NoError(t, err, "can't create first workspace")
-
-		// Secondly, create a new workspace using parameters from the previous workspace.
-		const otherWorkspace = "other-workspace"
-
-		inv, root = clitest.New(t, "create", "--copy-parameters-from", "my-workspace", otherWorkspace, "-y")
-		clitest.SetupConfig(t, member, root)
-		pty = ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err = inv.Run()
-		require.NoError(t, err, "can't create a workspace based on the source workspace")
-
-		// Verify if the new workspace uses expected parameters.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: otherWorkspace,
-		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		otherWorkspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, otherWorkspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
-
-	t.Run("CopyParametersFromNotUpdatedWorkspace", func(t *testing.T) {
-		t.Parallel()
-
-		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerDaemon: true})
-		owner := coderdtest.CreateFirstUser(t, client)
-		member, _ := coderdtest.CreateAnotherUser(t, client, owner.OrganizationID)
-		version := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, echoResponses())
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
-
-		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
-
-		// Firstly, create a regular workspace using template with parameters.
-		inv, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "-y",
-			"--parameter", fmt.Sprintf("%s=%s", firstParameterName, firstParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", secondParameterName, secondParameterValue),
-			"--parameter", fmt.Sprintf("%s=%s", immutableParameterName, immutableParameterValue))
-		clitest.SetupConfig(t, member, root)
-		pty := ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err := inv.Run()
-		require.NoError(t, err, "can't create first workspace")
-
-		// Secondly, update the template to the newer version.
-		version2 := coderdtest.CreateTemplateVersion(t, client, owner.OrganizationID, prepareEchoResponses([]*proto.RichParameter{
-			{Name: "third_parameter", Type: "string", DefaultValue: "not-relevant"},
-		}), func(ctvr *codersdk.CreateTemplateVersionRequest) {
-			ctvr.TemplateID = template.ID
-		})
-		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version2.ID)
-		coderdtest.UpdateActiveTemplateVersion(t, client, template.ID, version2.ID)
-
-		// Thirdly, create a new workspace using parameters from the previous workspace.
-		const otherWorkspace = "other-workspace"
-
-		inv, root = clitest.New(t, "create", "--copy-parameters-from", "my-workspace", otherWorkspace, "-y")
-		clitest.SetupConfig(t, member, root)
-		pty = ptytest.New(t).Attach(inv)
-		inv.Stdout = pty.Output()
-		inv.Stderr = pty.Output()
-		err = inv.Run()
-		require.NoError(t, err, "can't create a workspace based on the source workspace")
-
-		// Verify if the new workspace uses expected parameters.
-		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitShort)
-		defer cancel()
-
-		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
-			Name: otherWorkspace,
-		})
-		require.NoError(t, err, "can't list available workspaces")
-		require.Len(t, workspaces.Workspaces, 1)
-
-		otherWorkspaceLatestBuild := workspaces.Workspaces[0].LatestBuild
-		require.Equal(t, version.ID, otherWorkspaceLatestBuild.TemplateVersionID)
-
-		buildParameters, err := client.WorkspaceBuildParameters(ctx, otherWorkspaceLatestBuild.ID)
-		require.NoError(t, err)
-		require.Len(t, buildParameters, 3)
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: firstParameterName, Value: firstParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: secondParameterName, Value: secondParameterValue})
-		require.Contains(t, buildParameters, codersdk.WorkspaceBuildParameter{Name: immutableParameterName, Value: immutableParameterValue})
-	})
+	}
 }
 
 func TestCreateWithPreset(t *testing.T) {

cli/exp_boundary.go

@@ -1,18 +1,12 @@
 package cli
 
 import (
-	"golang.org/x/xerrors"
-
+	boundarycli "github.com/coder/boundary/cli"
 	"github.com/coder/serpent"
 )
 
 func (*RootCmd) boundary() *serpent.Command {
-	return &serpent.Command{
-		Use:   "boundary",
-		Short: "Network isolation tool for monitoring and restricting HTTP/HTTPS requests (enterprise)",
-		Long:  `boundary creates an isolated network environment for target processes. This is an enterprise feature.`,
-		Handler: func(_ *serpent.Invocation) error {
-			return xerrors.New("boundary is an enterprise feature; upgrade to use this command")
-		},
-	}
+	cmd := boundarycli.BaseCommand() // Package coder/boundary/cli exports a "base command" designed to be integrated as a subcommand.
+	cmd.Use += " [args...]"          // The base command looks like `boundary -- command`. Serpent adds the flags piece, but we need to add the args.
+	return cmd
 }

cli/exp_boundary_test.go

@@ -5,13 +5,15 @@ import (
 
 	"github.com/stretchr/testify/assert"
 
+	boundarycli "github.com/coder/boundary/cli"
 	"github.com/coder/coder/v2/cli/clitest"
 	"github.com/coder/coder/v2/pty/ptytest"
 	"github.com/coder/coder/v2/testutil"
 )
 
-// Here we want to test that integrating boundary as a subcommand doesn't break anything.
-// The full boundary functionality is tested in enterprise/cli.
+// Actually testing the functionality of coder/boundary takes place in the
+// coder/boundary repo, since it's a dependency of coder.
+// Here we want to test basically that integrating it as a subcommand doesn't break anything.
 func TestBoundarySubcommand(t *testing.T) {
 	t.Parallel()
 	ctx := testutil.Context(t, testutil.WaitShort)
@@ -25,5 +27,7 @@ func TestBoundarySubcommand(t *testing.T) {
 	}()
 
 	// Expect the --help output to include the short description.
-	pty.ExpectMatch("Network isolation tool")
+	// We're simply confirming that `coder boundary --help` ran without a runtime error as
+	// a good chunk of serpents self validation logic happens at runtime.
+	pty.ExpectMatch(boundarycli.BaseCommand().Short)
 }

cli/exp_scaletest.go

@@ -68,6 +68,8 @@ func (r *RootCmd) scaletestCmd() *serpent.Command {
 			r.scaletestTaskStatus(),
 			r.scaletestSMTP(),
 			r.scaletestPrebuilds(),
+			r.scaletestBridge(),
+			r.scaletestLLMMock(),
 		},
 	}
 

cli/exp_scaletest_bridge.go

@@ -0,0 +1,278 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"net/http"
+	"os/signal"
+	"strconv"
+	"text/tabwriter"
+	"time"
+
+	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/promhttp"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/v2/codersdk"
+	"github.com/coder/coder/v2/scaletest/bridge"
+	"github.com/coder/coder/v2/scaletest/createusers"
+	"github.com/coder/coder/v2/scaletest/harness"
+	"github.com/coder/serpent"
+)
+
+func (r *RootCmd) scaletestBridge() *serpent.Command {
+	var (
+		concurrentUsers    int64
+		noCleanup          bool
+		mode               string
+		upstreamURL        string
+		provider           string
+		requestsPerUser    int64
+		useStreamingAPI    bool
+		requestPayloadSize int64
+		numMessages        int64
+		httpTimeout        time.Duration
+
+		timeoutStrategy = &timeoutFlags{}
+		cleanupStrategy = newScaletestCleanupStrategy()
+		output          = &scaletestOutputFlags{}
+		prometheusFlags = &scaletestPrometheusFlags{}
+	)
+
+	cmd := &serpent.Command{
+		Use:   "bridge",
+		Short: "Generate load on the AI Bridge service.",
+		Long: `Generate load for AI Bridge testing. Supports two modes: 'bridge' mode routes requests through the Coder AI Bridge, 'direct' mode makes requests directly to an upstream URL (useful for baseline comparisons).
+
+Examples:
+  # Test OpenAI API through bridge
+  coder scaletest bridge --mode bridge --provider openai --concurrent-users 10 --request-count 5 --num-messages 10
+
+  # Test Anthropic API through bridge
+  coder scaletest bridge --mode bridge --provider anthropic --concurrent-users 10 --request-count 5 --num-messages 10
+
+  # Test directly against mock server
+  coder scaletest bridge --mode direct --provider openai --upstream-url http://localhost:8080/v1/chat/completions
+`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+			client, err := r.InitClient(inv)
+			if err != nil {
+				return err
+			}
+			client.HTTPClient = &http.Client{
+				Transport: &codersdk.HeaderTransport{
+					Transport: http.DefaultTransport,
+					Header: map[string][]string{
+						codersdk.BypassRatelimitHeader: {"true"},
+					},
+				},
+			}
+			reg := prometheus.NewRegistry()
+			metrics := bridge.NewMetrics(reg)
+
+			logger := inv.Logger
+			prometheusSrvClose := ServeHandler(ctx, logger, promhttp.HandlerFor(reg, promhttp.HandlerOpts{}), prometheusFlags.Address, "prometheus")
+			defer prometheusSrvClose()
+
+			defer func() {
+				_, _ = fmt.Fprintf(inv.Stderr, "Waiting %s for prometheus metrics to be scraped\n", prometheusFlags.Wait)
+				<-time.After(prometheusFlags.Wait)
+			}()
+
+			notifyCtx, stop := signal.NotifyContext(ctx, StopSignals...)
+			defer stop()
+			ctx = notifyCtx
+
+			var userConfig createusers.Config
+			if bridge.RequestMode(mode) == bridge.RequestModeBridge {
+				me, err := requireAdmin(ctx, client)
+				if err != nil {
+					return err
+				}
+				if len(me.OrganizationIDs) == 0 {
+					return xerrors.Errorf("admin user must have at least one organization")
+				}
+				userConfig = createusers.Config{
+					OrganizationID: me.OrganizationIDs[0],
+				}
+				_, _ = fmt.Fprintln(inv.Stderr, "Bridge mode: creating users and making requests through AI Bridge...")
+			} else {
+				_, _ = fmt.Fprintf(inv.Stderr, "Direct mode: making requests directly to %s\n", upstreamURL)
+			}
+
+			outputs, err := output.parse()
+			if err != nil {
+				return xerrors.Errorf("parse output flags: %w", err)
+			}
+
+			config := bridge.Config{
+				Mode:               bridge.RequestMode(mode),
+				Metrics:            metrics,
+				Provider:           provider,
+				RequestCount:       int(requestsPerUser),
+				Stream:             useStreamingAPI,
+				RequestPayloadSize: int(requestPayloadSize),
+				NumMessages:        int(numMessages),
+				HTTPTimeout:        httpTimeout,
+				UpstreamURL:        upstreamURL,
+				User:               userConfig,
+			}
+			if err := config.Validate(); err != nil {
+				return xerrors.Errorf("validate config: %w", err)
+			}
+			if err := config.PrepareRequestBody(); err != nil {
+				return xerrors.Errorf("prepare request body: %w", err)
+			}
+
+			th := harness.NewTestHarness(timeoutStrategy.wrapStrategy(harness.ConcurrentExecutionStrategy{}), cleanupStrategy.toStrategy())
+
+			for i := range concurrentUsers {
+				id := strconv.Itoa(int(i))
+				name := fmt.Sprintf("bridge-%s", id)
+				var runner harness.Runnable = bridge.NewRunner(client, config)
+				th.AddRun(name, id, runner)
+			}
+
+			_, _ = fmt.Fprintln(inv.Stderr, "Bridge scaletest configuration:")
+			tw := tabwriter.NewWriter(inv.Stderr, 0, 0, 2, ' ', 0)
+			for _, opt := range inv.Command.Options {
+				if opt.Hidden || opt.ValueSource == serpent.ValueSourceNone {
+					continue
+				}
+				_, _ = fmt.Fprintf(tw, "  %s:\t%s", opt.Name, opt.Value.String())
+				if opt.ValueSource != serpent.ValueSourceDefault {
+					_, _ = fmt.Fprintf(tw, "\t(from %s)", opt.ValueSource)
+				}
+				_, _ = fmt.Fprintln(tw)
+			}
+			_ = tw.Flush()
+
+			_, _ = fmt.Fprintln(inv.Stderr, "\nRunning bridge scaletest...")
+			testCtx, testCancel := timeoutStrategy.toContext(ctx)
+			defer testCancel()
+			err = th.Run(testCtx)
+			if err != nil {
+				return xerrors.Errorf("run test harness (harness failure, not a test failure): %w", err)
+			}
+
+			// If the command was interrupted, skip stats.
+			if notifyCtx.Err() != nil {
+				return notifyCtx.Err()
+			}
+
+			res := th.Results()
+
+			for _, o := range outputs {
+				err = o.write(res, inv.Stdout)
+				if err != nil {
+					return xerrors.Errorf("write output %q to %q: %w", o.format, o.path, err)
+				}
+			}
+
+			if !noCleanup {
+				_, _ = fmt.Fprintln(inv.Stderr, "\nCleaning up...")
+				cleanupCtx, cleanupCancel := cleanupStrategy.toContext(ctx)
+				defer cleanupCancel()
+				err = th.Cleanup(cleanupCtx)
+				if err != nil {
+					return xerrors.Errorf("cleanup tests: %w", err)
+				}
+			}
+
+			if res.TotalFail > 0 {
+				return xerrors.New("load test failed, see above for more details")
+			}
+
+			return nil
+		},
+	}
+
+	cmd.Options = serpent.OptionSet{
+		{
+			Flag:          "concurrent-users",
+			FlagShorthand: "c",
+			Env:           "CODER_SCALETEST_BRIDGE_CONCURRENT_USERS",
+			Description:   "Required: Number of concurrent users.",
+			Value: serpent.Validate(serpent.Int64Of(&concurrentUsers), func(value *serpent.Int64) error {
+				if value == nil || value.Value() <= 0 {
+					return xerrors.Errorf("--concurrent-users must be greater than 0")
+				}
+				return nil
+			}),
+			Required: true,
+		},
+		{
+			Flag:        "mode",
+			Env:         "CODER_SCALETEST_BRIDGE_MODE",
+			Default:     "direct",
+			Description: "Request mode: 'bridge' (create users and use AI Bridge) or 'direct' (make requests directly to upstream-url).",
+			Value:       serpent.EnumOf(&mode, string(bridge.RequestModeBridge), string(bridge.RequestModeDirect)),
+		},
+		{
+			Flag:        "upstream-url",
+			Env:         "CODER_SCALETEST_BRIDGE_UPSTREAM_URL",
+			Description: "URL to make requests to directly (required in direct mode, e.g., http://localhost:8080/v1/chat/completions).",
+			Value:       serpent.StringOf(&upstreamURL),
+		},
+		{
+			Flag:        "provider",
+			Env:         "CODER_SCALETEST_BRIDGE_PROVIDER",
+			Default:     "openai",
+			Description: "API provider to use.",
+			Value:       serpent.EnumOf(&provider, "openai", "anthropic"),
+		},
+		{
+			Flag:        "request-count",
+			Env:         "CODER_SCALETEST_BRIDGE_REQUEST_COUNT",
+			Default:     "1",
+			Description: "Number of sequential requests to make per runner.",
+			Value: serpent.Validate(serpent.Int64Of(&requestsPerUser), func(value *serpent.Int64) error {
+				if value == nil || value.Value() <= 0 {
+					return xerrors.Errorf("--request-count must be greater than 0")
+				}
+				return nil
+			}),
+		},
+		{
+			Flag:        "stream",
+			Env:         "CODER_SCALETEST_BRIDGE_STREAM",
+			Description: "Enable streaming requests.",
+			Value:       serpent.BoolOf(&useStreamingAPI),
+		},
+		{
+			Flag:        "request-payload-size",
+			Env:         "CODER_SCALETEST_BRIDGE_REQUEST_PAYLOAD_SIZE",
+			Default:     "1024",
+			Description: "Size in bytes of the request payload (user message content). If 0, uses default message content.",
+			Value:       serpent.Int64Of(&requestPayloadSize),
+		},
+		{
+			Flag:        "num-messages",
+			Env:         "CODER_SCALETEST_BRIDGE_NUM_MESSAGES",
+			Default:     "1",
+			Description: "Number of messages to include in the conversation.",
+			Value:       serpent.Int64Of(&numMessages),
+		},
+		{
+			Flag:        "no-cleanup",
+			Env:         "CODER_SCALETEST_NO_CLEANUP",
+			Description: "Do not clean up resources after the test completes.",
+			Value:       serpent.BoolOf(&noCleanup),
+		},
+		{
+			Flag:        "http-timeout",
+			Env:         "CODER_SCALETEST_BRIDGE_HTTP_TIMEOUT",
+			Default:     "30s",
+			Description: "Timeout for individual HTTP requests to the upstream provider.",
+			Value:       serpent.DurationOf(&httpTimeout),
+		},
+	}
+
+	timeoutStrategy.attach(&cmd.Options)
+	cleanupStrategy.attach(&cmd.Options)
+	output.attach(&cmd.Options)
+	prometheusFlags.attach(&cmd.Options)
+	return cmd
+}

cli/exp_scaletest_llmmock.go

@@ -0,0 +1,118 @@
+//go:build !slim
+
+package cli
+
+import (
+	"fmt"
+	"os/signal"
+	"time"
+
+	"golang.org/x/xerrors"
+
+	"cdr.dev/slog/v3"
+	"cdr.dev/slog/v3/sloggers/sloghuman"
+	"github.com/coder/coder/v2/scaletest/llmmock"
+	"github.com/coder/serpent"
+)
+
+func (*RootCmd) scaletestLLMMock() *serpent.Command {
+	var (
+		address             string
+		artificialLatency   time.Duration
+		responsePayloadSize int64
+
+		pprofEnable  bool
+		pprofAddress string
+
+		traceEnable bool
+	)
+	cmd := &serpent.Command{
+		Use:   "llm-mock",
+		Short: "Start a mock LLM API server for testing",
+		Long:  `Start a mock LLM API server that simulates OpenAI and Anthropic APIs`,
+		Handler: func(inv *serpent.Invocation) error {
+			ctx, stop := signal.NotifyContext(inv.Context(), StopSignals...)
+			defer stop()
+
+			logger := slog.Make(sloghuman.Sink(inv.Stderr)).Leveled(slog.LevelInfo)
+
+			if pprofEnable {
+				closePprof := ServeHandler(ctx, logger, nil, pprofAddress, "pprof")
+				defer closePprof()
+				logger.Info(ctx, "pprof server started", slog.F("address", pprofAddress))
+			}
+
+			config := llmmock.Config{
+				Address:             address,
+				Logger:              logger,
+				ArtificialLatency:   artificialLatency,
+				ResponsePayloadSize: int(responsePayloadSize),
+				PprofEnable:         pprofEnable,
+				PprofAddress:        pprofAddress,
+				TraceEnable:         traceEnable,
+			}
+			srv := new(llmmock.Server)
+
+			if err := srv.Start(ctx, config); err != nil {
+				return xerrors.Errorf("start mock LLM server: %w", err)
+			}
+			defer func() {
+				_ = srv.Stop()
+			}()
+
+			_, _ = fmt.Fprintf(inv.Stdout, "Mock LLM API server started on %s\n", srv.APIAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "  OpenAI endpoint: %s/v1/chat/completions\n", srv.APIAddress())
+			_, _ = fmt.Fprintf(inv.Stdout, "  Anthropic endpoint: %s/v1/messages\n", srv.APIAddress())
+
+			<-ctx.Done()
+			return nil
+		},
+	}
+
+	cmd.Options = []serpent.Option{
+		{
+			Flag:        "address",
+			Env:         "CODER_SCALETEST_LLM_MOCK_ADDRESS",
+			Default:     "localhost",
+			Description: "Address to bind the mock LLM API server. Can include a port (e.g., 'localhost:8080' or ':8080'). Uses a random port if no port is specified.",
+			Value:       serpent.StringOf(&address),
+		},
+		{
+			Flag:        "artificial-latency",
+			Env:         "CODER_SCALETEST_LLM_MOCK_ARTIFICIAL_LATENCY",
+			Default:     "0s",
+			Description: "Artificial latency to add to each response (e.g., 100ms, 1s). Simulates slow upstream processing.",
+			Value:       serpent.DurationOf(&artificialLatency),
+		},
+		{
+			Flag:        "response-payload-size",
+			Env:         "CODER_SCALETEST_LLM_MOCK_RESPONSE_PAYLOAD_SIZE",
+			Default:     "0",
+			Description: "Size in bytes of the response payload. If 0, uses default context-aware responses.",
+			Value:       serpent.Int64Of(&responsePayloadSize),
+		},
+		{
+			Flag:        "pprof-enable",
+			Env:         "CODER_SCALETEST_LLM_MOCK_PPROF_ENABLE",
+			Default:     "false",
+			Description: "Serve pprof metrics on the address defined by pprof-address.",
+			Value:       serpent.BoolOf(&pprofEnable),
+		},
+		{
+			Flag:        "pprof-address",
+			Env:         "CODER_SCALETEST_LLM_MOCK_PPROF_ADDRESS",
+			Default:     "127.0.0.1:6060",
+			Description: "The bind address to serve pprof.",
+			Value:       serpent.StringOf(&pprofAddress),
+		},
+		{
+			Flag:        "trace-enable",
+			Env:         "CODER_SCALETEST_LLM_MOCK_TRACE_ENABLE",
+			Default:     "false",
+			Description: "Whether application tracing data is collected. It exports to a backend configured by environment variables. See: https://github.com/open-telemetry/opentelemetry-specification/blob/main/specification/protocol/exporter.md.",
+			Value:       serpent.BoolOf(&traceEnable),
+		},
+	}
+
+	return cmd
+}

cli/organizationsettings.go

@@ -65,6 +65,22 @@ func (r *RootCmd) organizationSettings(orgContext *OrganizationContext) *serpent
 				return cli.OrganizationIDPSyncSettings(ctx)
 			},
 		},
+		{
+			Name:    "workspace-sharing",
+			Aliases: []string{"workspacesharing"},
+			Short:   "Workspace sharing settings for the organization.",
+			Patch: func(ctx context.Context, cli *codersdk.Client, org uuid.UUID, input json.RawMessage) (any, error) {
+				var req codersdk.WorkspaceSharingSettings
+				err := json.Unmarshal(input, &req)
+				if err != nil {
+					return nil, xerrors.Errorf("unmarshalling workspace sharing settings: %w", err)
+				}
+				return cli.PatchWorkspaceSharingSettings(ctx, org.String(), req)
+			},
+			Fetch: func(ctx context.Context, cli *codersdk.Client, org uuid.UUID) (any, error) {
+				return cli.WorkspaceSharingSettings(ctx, org.String())
+			},
+		},
 	}
 	cmd := &serpent.Command{
 		Use:     "settings",

cli/parameterresolver.go

@@ -34,6 +34,7 @@ type ParameterResolver struct {
 
 	promptRichParameters      bool
 	promptEphemeralParameters bool
+	useParameterDefaults      bool
 }
 
 func (pr *ParameterResolver) WithLastBuildParameters(params []codersdk.WorkspaceBuildParameter) *ParameterResolver {
@@ -86,8 +87,21 @@ func (pr *ParameterResolver) WithPromptEphemeralParameters(promptEphemeralParame
 	return pr
 }
 
-// Resolve gathers workspace build parameters in a layered fashion, applying values from various sources
-// in order of precedence: parameter file < CLI/ENV < source build < last build < preset < user input.
+func (pr *ParameterResolver) WithUseParameterDefaults(useParameterDefaults bool) *ParameterResolver {
+	pr.useParameterDefaults = useParameterDefaults
+	return pr
+}
+
+// Resolve gathers workspace build parameters in a layered fashion, applying
+// values from various sources in order of precedence:
+// 1. template defaults (if auto-accepting defaults)
+// 2. cli parameter defaults (if auto-accepting defaults)
+// 3. parameter file
+// 4. CLI/ENV
+// 5. source build
+// 6. last build
+// 7. preset
+// 8. user input (unless auto-accepting defaults)
 func (pr *ParameterResolver) Resolve(inv *serpent.Invocation, action WorkspaceCLIAction, templateVersionParameters []codersdk.TemplateVersionParameter) ([]codersdk.WorkspaceBuildParameter, error) {
 	var staged []codersdk.WorkspaceBuildParameter
 	var err error
@@ -262,9 +276,25 @@ func (pr *ParameterResolver) resolveWithInput(resolved []codersdk.WorkspaceBuild
 			(action == WorkspaceUpdate && tvp.Mutable && tvp.Required) ||
 			(action == WorkspaceUpdate && !tvp.Mutable && firstTimeUse) ||
 			(tvp.Mutable && !tvp.Ephemeral && pr.promptRichParameters) {
-			parameterValue, err := cliui.RichParameter(inv, tvp, pr.richParametersDefaults)
-			if err != nil {
-				return nil, err
+			name := tvp.Name
+			if tvp.DisplayName != "" {
+				name = tvp.DisplayName
+			}
+
+			parameterValue := tvp.DefaultValue
+			if v, ok := pr.richParametersDefaults[tvp.Name]; ok {
+				parameterValue = v
+			}
+
+			// Auto-accept the default if there is one.
+			if pr.useParameterDefaults && parameterValue != "" {
+				_, _ = fmt.Fprintf(inv.Stdout, "Using default value for %s: '%s'\n", name, parameterValue)
+			} else {
+				var err error
+				parameterValue, err = cliui.RichParameter(inv, tvp, name, parameterValue)
+				if err != nil {
+					return nil, err
+				}
 			}
 
 			resolved = append(resolved, codersdk.WorkspaceBuildParameter{

cli/root.go

@@ -24,6 +24,7 @@ import (
 	"text/tabwriter"
 	"time"
 
+	"github.com/google/uuid"
 	"github.com/mattn/go-isatty"
 	"github.com/mitchellh/go-wordwrap"
 	"golang.org/x/mod/semver"
@@ -923,6 +924,9 @@ func splitNamedWorkspace(identifier string) (owner string, workspaceName string,
 // a bare name (for a workspace owned by the current user) or a "user/workspace" combination,
 // where user is either a username or UUID.
 func namedWorkspace(ctx context.Context, client *codersdk.Client, identifier string) (codersdk.Workspace, error) {
+	if uid, err := uuid.Parse(identifier); err == nil {
+		return client.Workspace(ctx, uid)
+	}
 	owner, name, err := splitNamedWorkspace(identifier)
 	if err != nil {
 		return codersdk.Workspace{}, err

cli/server.go

@@ -865,6 +865,14 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 			if err != nil {
 				return xerrors.Errorf("remove secrets from deployment values: %w", err)
 			}
+
+			// Create boundary telemetry collector for tracking boundary feature usage.
+			boundaryTelemetryCollector := telemetry.NewBoundaryTelemetryCollector(
+				options.Database,
+				logger.Named("boundary_telemetry"),
+			)
+			options.BoundaryTelemetryCollector = boundaryTelemetryCollector
+
 			telemetryReporter, err := telemetry.New(telemetry.Options{
 				Disabled:         !vals.Telemetry.Enable.Value(),
 				BuiltinPostgres:  builtinPostgres,
@@ -873,8 +881,9 @@ func (r *RootCmd) Server(newAPI func(context.Context, *coderd.Options) (*coderd.
 				Experiments:      coderd.ReadExperiments(options.Logger, options.DeploymentValues.Experiments.Value()),
 				Logger:           logger.Named("telemetry"),
 				URL:              vals.Telemetry.URL.Value(),
-				Tunnel:           tunnel != nil,
-				DeploymentConfig: deploymentConfigWithoutSecrets,
+				Tunnel:                     tunnel != nil,
+				DeploymentConfig:           deploymentConfigWithoutSecrets,
+				BoundaryTelemetryCollector: boundaryTelemetryCollector,
 				ParseLicenseJWT: func(lic *telemetry.License) error {
 					// This will be nil when running in AGPL-only mode.
 					if options.ParseLicenseClaims == nil {

cli/show.go

@@ -1,8 +1,10 @@
 package cli
 
 import (
+	"fmt"
 	"sort"
 	"sync"
+	"time"
 
 	"github.com/google/uuid"
 	"golang.org/x/xerrors"
@@ -43,11 +45,11 @@ func (r *RootCmd) show() *serpent.Command {
 			if err != nil {
 				return xerrors.Errorf("get workspace: %w", err)
 			}
-
 			options := cliui.WorkspaceResourcesOptions{
 				WorkspaceName: workspace.Name,
 				ServerVersion: buildInfo.Version,
 				ShowDetails:   details,
+				Title:         fmt.Sprintf("%s/%s (%s since %s) %s:%s", workspace.OwnerName, workspace.Name, workspace.LatestBuild.Status, time.Since(workspace.LatestBuild.CreatedAt).Round(time.Second).String(), workspace.TemplateName, workspace.LatestBuild.TemplateVersionName),
 			}
 			if workspace.LatestBuild.Status == codersdk.WorkspaceStatusRunning {
 				// Get listening ports for each agent.
@@ -55,7 +57,6 @@ func (r *RootCmd) show() *serpent.Command {
 				options.ListeningPorts = ports
 				options.Devcontainers = devcontainers
 			}
-
 			return cliui.WorkspaceResources(inv.Stdout, workspace.LatestBuild.Resources, options)
 		},
 	}

cli/show_test.go

@@ -2,6 +2,7 @@ package cli_test
 
 import (
 	"bytes"
+	"fmt"
 	"testing"
 	"time"
 
@@ -15,6 +16,7 @@ import (
 	"github.com/coder/coder/v2/coderd/coderdtest"
 	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/pty/ptytest"
+	"github.com/coder/coder/v2/testutil"
 )
 
 func TestShow(t *testing.T) {
@@ -28,7 +30,7 @@ func TestShow(t *testing.T) {
 		coderdtest.AwaitTemplateVersionJobCompleted(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, owner.OrganizationID, version.ID)
 		workspace := coderdtest.CreateWorkspace(t, member, template.ID)
-		coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
+		build := coderdtest.AwaitWorkspaceBuildJobCompleted(t, client, workspace.LatestBuild.ID)
 
 		args := []string{
 			"show",
@@ -38,26 +40,30 @@ func TestShow(t *testing.T) {
 		clitest.SetupConfig(t, member, root)
 		doneChan := make(chan struct{})
 		pty := ptytest.New(t).Attach(inv)
+		ctx := testutil.Context(t, testutil.WaitShort)
 		go func() {
 			defer close(doneChan)
-			err := inv.Run()
+			err := inv.WithContext(ctx).Run()
 			assert.NoError(t, err)
 		}()
 		matches := []struct {
 			match string
 			write string
 		}{
+			{match: fmt.Sprintf("%s/%s", workspace.OwnerName, workspace.Name)},
+			{match: fmt.Sprintf("(%s since ", build.Status)},
+			{match: fmt.Sprintf("%s:%s", workspace.TemplateName, workspace.LatestBuild.TemplateVersionName)},
 			{match: "compute.main"},
 			{match: "smith (linux, i386)"},
 			{match: "coder ssh " + workspace.Name},
 		}
 		for _, m := range matches {
-			pty.ExpectMatch(m.match)
+			pty.ExpectMatchContext(ctx, m.match)
 			if len(m.write) > 0 {
 				pty.WriteLine(m.write)
 			}
 		}
-		<-doneChan
+		_ = testutil.TryReceive(ctx, t, doneChan)
 	})
 }
 

cli/support.go

@@ -7,6 +7,7 @@ import (
 	"encoding/base64"
 	"encoding/json"
 	"fmt"
+	"net/http"
 	"net/url"
 	"os"
 	"path/filepath"
@@ -44,13 +45,18 @@ var supportBundleBlurb = cliui.Bold("This will collect the following information
 	`  - Coder deployment version
   - Coder deployment Configuration (sanitized), including enabled experiments
   - Coder deployment health snapshot
+  - Coder deployment stats (aggregated workspace/session metrics)
+  - Entitlements (if available)
+  - Health settings (dismissed healthchecks)
   - Coder deployment Network troubleshooting information
+  - Workspace list accessible to the user (sanitized)
   - Workspace configuration, parameters, and build logs
   - Template version and source code for the given workspace
   - Agent details (with environment variable sanitized)
   - Agent network diagnostics
   - Agent logs
   - License status
+  - pprof profiling data (if --pprof is enabled)
 ` + cliui.Bold("Note: ") +
 	cliui.Wrap("While we try to sanitize sensitive data from support bundles, we cannot guarantee that they do not contain information that you or your organization may consider sensitive.\n") +
 	cliui.Bold("Please confirm that you will:\n") +
@@ -61,6 +67,9 @@ var supportBundleBlurb = cliui.Bold("This will collect the following information
 func (r *RootCmd) supportBundle() *serpent.Command {
 	var outputPath string
 	var coderURLOverride string
+	var workspacesTotalCap64 int64 = 10
+	var templateName string
+	var pprof bool
 	cmd := &serpent.Command{
 		Use:   "bundle <workspace> [<agent>]",
 		Short: "Generate a support bundle to troubleshoot issues connecting to a workspace.",
@@ -121,8 +130,9 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			}
 
 			var (
-				wsID  uuid.UUID
-				agtID uuid.UUID
+				wsID       uuid.UUID
+				agtID      uuid.UUID
+				templateID uuid.UUID
 			)
 
 			if len(inv.Args) == 0 {
@@ -155,6 +165,16 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 				}
 			}
 
+			// Resolve template by name if provided (captures active version)
+			// Fallback: if canonical name lookup fails, match DisplayName (case-insensitive).
+			if templateName != "" {
+				id, err := resolveTemplateID(inv.Context(), client, templateName)
+				if err != nil {
+					return err
+				}
+				templateID = id
+			}
+
 			if outputPath == "" {
 				cwd, err := filepath.Abs(".")
 				if err != nil {
@@ -176,12 +196,25 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			if r.verbose {
 				clientLog.AppendSinks(sloghuman.Sink(inv.Stderr))
 			}
+			if pprof {
+				_, _ = fmt.Fprintln(inv.Stderr, "pprof data collection will take approximately 30 seconds...")
+			}
+
+			// Bypass rate limiting for support bundle collection since it makes many API calls.
+			client.HTTPClient.Transport = &codersdk.HeaderTransport{
+				Transport: client.HTTPClient.Transport,
+				Header:    http.Header{codersdk.BypassRatelimitHeader: {"true"}},
+			}
+
 			deps := support.Deps{
 				Client: client,
 				// Support adds a sink so we don't need to supply one ourselves.
-				Log:         clientLog,
-				WorkspaceID: wsID,
-				AgentID:     agtID,
+				Log:                clientLog,
+				WorkspaceID:        wsID,
+				AgentID:            agtID,
+				WorkspacesTotalCap: int(workspacesTotalCap64),
+				TemplateID:         templateID,
+				CollectPprof:       pprof,
 			}
 
 			bun, err := support.Run(inv.Context(), &deps)
@@ -217,11 +250,102 @@ func (r *RootCmd) supportBundle() *serpent.Command {
 			Description: "Override the URL to your Coder deployment. This may be useful, for example, if you need to troubleshoot a specific Coder replica.",
 			Value:       serpent.StringOf(&coderURLOverride),
 		},
+		{
+			Flag:        "workspaces-total-cap",
+			Env:         "CODER_SUPPORT_BUNDLE_WORKSPACES_TOTAL_CAP",
+			Description: "Maximum number of workspaces to include in the support bundle. Set to 0 or negative value to disable the cap. Defaults to 10.",
+			Value:       serpent.Int64Of(&workspacesTotalCap64),
+		},
+		{
+			Flag:        "template",
+			Env:         "CODER_SUPPORT_BUNDLE_TEMPLATE",
+			Description: "Template name to include in the support bundle. Use org_name/template_name if template name is reused across multiple organizations.",
+			Value:       serpent.StringOf(&templateName),
+		},
+		{
+			Flag:        "pprof",
+			Env:         "CODER_SUPPORT_BUNDLE_PPROF",
+			Description: "Collect pprof profiling data from the Coder server and agent. Requires Coder server version 2.28.0 or newer.",
+			Value:       serpent.BoolOf(&pprof),
+		},
 	}
 
 	return cmd
 }
 
+// Resolve a template to its ID, supporting:
+// - org/name form
+// - slug or display name match (case-insensitive) across all memberships
+func resolveTemplateID(ctx context.Context, client *codersdk.Client, templateArg string) (uuid.UUID, error) {
+	orgPart := ""
+	namePart := templateArg
+	if slash := strings.IndexByte(templateArg, '/'); slash > 0 && slash < len(templateArg)-1 {
+		orgPart = templateArg[:slash]
+		namePart = templateArg[slash+1:]
+	}
+
+	resolveInOrg := func(orgID uuid.UUID) (codersdk.Template, bool, error) {
+		if t, err := client.TemplateByName(ctx, orgID, namePart); err == nil {
+			return t, true, nil
+		}
+		tpls, err := client.TemplatesByOrganization(ctx, orgID)
+		if err != nil {
+			return codersdk.Template{}, false, nil
+		}
+		for _, t := range tpls {
+			if strings.EqualFold(t.Name, namePart) || strings.EqualFold(t.DisplayName, namePart) {
+				return t, true, nil
+			}
+		}
+		return codersdk.Template{}, false, nil
+	}
+
+	if orgPart != "" {
+		org, err := client.OrganizationByName(ctx, orgPart)
+		if err != nil {
+			return uuid.Nil, xerrors.Errorf("get organization %q: %w", orgPart, err)
+		}
+		t, found, err := resolveInOrg(org.ID)
+		if err != nil {
+			return uuid.Nil, err
+		}
+		if !found {
+			return uuid.Nil, xerrors.Errorf("template %q not found in organization %q", namePart, orgPart)
+		}
+		return t.ID, nil
+	}
+
+	orgs, err := client.OrganizationsByUser(ctx, codersdk.Me)
+	if err != nil {
+		return uuid.Nil, xerrors.Errorf("get organizations: %w", err)
+	}
+	var (
+		foundTpl  codersdk.Template
+		foundOrgs []string
+	)
+	for _, org := range orgs {
+		if t, found, err := resolveInOrg(org.ID); err == nil && found {
+			if len(foundOrgs) == 0 {
+				foundTpl = t
+			}
+			foundOrgs = append(foundOrgs, org.Name)
+		}
+	}
+	switch len(foundOrgs) {
+	case 0:
+		return uuid.Nil, xerrors.Errorf("template %q not found in your organizations", namePart)
+	case 1:
+		return foundTpl.ID, nil
+	default:
+		return uuid.Nil, xerrors.Errorf(
+			"template %q found in multiple organizations (%s); use --template \"<org_name/%s>\" to target desired template.",
+			namePart,
+			strings.Join(foundOrgs, ", "),
+			namePart,
+		)
+	}
+}
+
 // summarizeBundle makes a best-effort attempt to write a short summary
 // of the support bundle to the user's terminal.
 func summarizeBundle(inv *serpent.Invocation, bun *support.Bundle) {
@@ -283,6 +407,10 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		"deployment/config.json":          src.Deployment.Config,
 		"deployment/experiments.json":     src.Deployment.Experiments,
 		"deployment/health.json":          src.Deployment.HealthReport,
+		"deployment/stats.json":           src.Deployment.Stats,
+		"deployment/entitlements.json":    src.Deployment.Entitlements,
+		"deployment/health_settings.json": src.Deployment.HealthSettings,
+		"deployment/workspaces.json":      src.Deployment.Workspaces,
 		"network/connection_info.json":    src.Network.ConnectionInfo,
 		"network/netcheck.json":           src.Network.Netcheck,
 		"network/interfaces.json":         src.Network.Interfaces,
@@ -302,6 +430,49 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		}
 	}
 
+	// Include named template artifacts (if requested)
+	if src.NamedTemplate.Template.ID != uuid.Nil {
+		name := src.NamedTemplate.Template.Name
+		// JSON files
+		for k, v := range map[string]any{
+			"templates/" + name + "/template.json":         src.NamedTemplate.Template,
+			"templates/" + name + "/template_version.json": src.NamedTemplate.TemplateVersion,
+		} {
+			f, err := dest.Create(k)
+			if err != nil {
+				return xerrors.Errorf("create file %q in archive: %w", k, err)
+			}
+			enc := json.NewEncoder(f)
+			enc.SetIndent("", "    ")
+			if err := enc.Encode(v); err != nil {
+				return xerrors.Errorf("write json to %q: %w", k, err)
+			}
+		}
+		// Binary template file (zip)
+		if namedZipBytes, err := base64.StdEncoding.DecodeString(src.NamedTemplate.TemplateFileBase64); err == nil {
+			k := "templates/" + name + "/template_file.zip"
+			f, err := dest.Create(k)
+			if err != nil {
+				return xerrors.Errorf("create file %q in archive: %w", k, err)
+			}
+			if _, err := f.Write(namedZipBytes); err != nil {
+				return xerrors.Errorf("write file %q in archive: %w", k, err)
+			}
+		}
+	}
+
+	var buildInfoRef string
+	if src.Deployment.BuildInfo != nil {
+		if raw, err := json.Marshal(src.Deployment.BuildInfo); err == nil {
+			buildInfoRef = base64.StdEncoding.EncodeToString(raw)
+		}
+	}
+
+	tailnetHTML := src.Network.TailnetDebug
+	if buildInfoRef != "" {
+		tailnetHTML += "\n<!-- trace " + buildInfoRef + " -->"
+	}
+
 	templateVersionBytes, err := base64.StdEncoding.DecodeString(src.Workspace.TemplateFileBase64)
 	if err != nil {
 		return xerrors.Errorf("decode template zip from base64")
@@ -319,10 +490,11 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 		"agent/client_magicsock.html":    string(src.Agent.ClientMagicsockHTML),
 		"agent/startup_logs.txt":         humanizeAgentLogs(src.Agent.StartupLogs),
 		"agent/prometheus.txt":           string(src.Agent.Prometheus),
+		"deployment/prometheus.txt":      string(src.Deployment.Prometheus),
 		"cli_logs.txt":                   string(src.CLILogs),
 		"logs.txt":                       strings.Join(src.Logs, "\n"),
 		"network/coordinator_debug.html": src.Network.CoordinatorDebug,
-		"network/tailnet_debug.html":     src.Network.TailnetDebug,
+		"network/tailnet_debug.html":     tailnetHTML,
 		"workspace/build_logs.txt":       humanizeBuildLogs(src.Workspace.BuildLogs),
 		"workspace/template_file.zip":    string(templateVersionBytes),
 		"license-status.txt":             licenseStatus,
@@ -335,12 +507,89 @@ func writeBundle(src *support.Bundle, dest *zip.Writer) error {
 			return xerrors.Errorf("write file %q in archive: %w", k, err)
 		}
 	}
+
+	// Write pprof binary data
+	if err := writePprofData(src.Pprof, dest); err != nil {
+		return xerrors.Errorf("write pprof data: %w", err)
+	}
+
 	if err := dest.Close(); err != nil {
 		return xerrors.Errorf("close zip file: %w", err)
 	}
 	return nil
 }
 
+func writePprofData(pprof support.Pprof, dest *zip.Writer) error {
+	// Write server pprof data directly to pprof directory
+	if pprof.Server != nil {
+		if err := writePprofCollection("pprof", pprof.Server, dest); err != nil {
+			return xerrors.Errorf("write server pprof data: %w", err)
+		}
+	}
+
+	// Write agent pprof data
+	if pprof.Agent != nil {
+		if err := writePprofCollection("pprof/agent", pprof.Agent, dest); err != nil {
+			return xerrors.Errorf("write agent pprof data: %w", err)
+		}
+	}
+
+	return nil
+}
+
+func writePprofCollection(basePath string, collection *support.PprofCollection, dest *zip.Writer) error {
+	// Define the pprof files to write with their extensions
+	files := map[string][]byte{
+		"allocs.prof.gz":       collection.Allocs,
+		"heap.prof.gz":         collection.Heap,
+		"profile.prof.gz":      collection.Profile,
+		"block.prof.gz":        collection.Block,
+		"mutex.prof.gz":        collection.Mutex,
+		"goroutine.prof.gz":    collection.Goroutine,
+		"threadcreate.prof.gz": collection.Threadcreate,
+		"trace.gz":             collection.Trace,
+	}
+
+	// Write binary pprof files
+	for filename, data := range files {
+		if len(data) > 0 {
+			filePath := basePath + "/" + filename
+			f, err := dest.Create(filePath)
+			if err != nil {
+				return xerrors.Errorf("create pprof file %q: %w", filePath, err)
+			}
+			if _, err := f.Write(data); err != nil {
+				return xerrors.Errorf("write pprof file %q: %w", filePath, err)
+			}
+		}
+	}
+
+	// Write cmdline as text file
+	if collection.Cmdline != "" {
+		filePath := basePath + "/cmdline.txt"
+		f, err := dest.Create(filePath)
+		if err != nil {
+			return xerrors.Errorf("create cmdline file %q: %w", filePath, err)
+		}
+		if _, err := f.Write([]byte(collection.Cmdline)); err != nil {
+			return xerrors.Errorf("write cmdline file %q: %w", filePath, err)
+		}
+	}
+
+	if collection.Symbol != "" {
+		filePath := basePath + "/symbol.txt"
+		f, err := dest.Create(filePath)
+		if err != nil {
+			return xerrors.Errorf("create symbol file %q: %w", filePath, err)
+		}
+		if _, err := f.Write([]byte(collection.Symbol)); err != nil {
+			return xerrors.Errorf("write symbol file %q: %w", filePath, err)
+		}
+	}
+
+	return nil
+}
+
 func humanizeAgentLogs(ls []codersdk.WorkspaceAgentLog) string {
 	var buf bytes.Buffer
 	tw := tabwriter.NewWriter(&buf, 0, 2, 1, ' ', 0)

cli/support_test.go

@@ -46,6 +46,8 @@ func TestSupportBundle(t *testing.T) {
 
 	// Support bundle tests can share a single coderdtest instance.
 	var dc codersdk.DeploymentConfig
+	dc.Values = coderdtest.DeploymentValues(t)
+	dc.Values.Prometheus.Enable = true
 	secretValue := uuid.NewString()
 	seedSecretDeploymentOptions(t, &dc, secretValue)
 	client, closer, api := coderdtest.NewWithAPI(t, &coderdtest.Options{
@@ -203,6 +205,10 @@ func assertBundleContents(t *testing.T, path string, wantWorkspace bool, wantAge
 			var v codersdk.DeploymentConfig
 			decodeJSONFromZip(t, f, &v)
 			require.NotEmpty(t, v, "deployment config should not be empty")
+		case "deployment/entitlements.json":
+			var v codersdk.Entitlements
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "entitlements should not be nil")
 		case "deployment/experiments.json":
 			var v codersdk.Experiments
 			decodeJSONFromZip(t, f, &v)
@@ -211,6 +217,22 @@ func assertBundleContents(t *testing.T, path string, wantWorkspace bool, wantAge
 			var v healthsdk.HealthcheckReport
 			decodeJSONFromZip(t, f, &v)
 			require.NotEmpty(t, v, "health report should not be empty")
+		case "deployment/health_settings.json":
+			var v healthsdk.HealthSettings
+			decodeJSONFromZip(t, f, &v)
+			require.NotEmpty(t, v, "health settings should not be empty")
+		case "deployment/stats.json":
+			var v codersdk.DeploymentStats
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "deployment stats should not be nil")
+		case "deployment/workspaces.json":
+			var v codersdk.Workspace
+			decodeJSONFromZip(t, f, &v)
+			require.NotNil(t, v, "deployment workspaces should not be nil")
+		case "deployment/prometheus.txt":
+			bs := readBytesFromZip(t, f)
+			require.NotEmpty(t, bs, "prometheus metrics should not be empty")
+			require.Contains(t, string(bs), "go_goroutines", "prometheus metrics should contain go runtime metrics")
 		case "network/connection_info.json":
 			var v workspacesdk.AgentConnectionInfo
 			decodeJSONFromZip(t, f, &v)

cli/testdata/coder_autoupdate_--help.golden

@@ -7,7 +7,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_config-ssh_--help.golden

@@ -55,7 +55,7 @@ OPTIONS:
           configured in the workspace template is used.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_create_--help.golden

@@ -49,8 +49,11 @@ OPTIONS:
       --template-version string, $CODER_TEMPLATE_VERSION
           Specify a template version name.
 
+      --use-parameter-defaults bool, $CODER_WORKSPACE_USE_PARAMETER_DEFAULTS
+          Automatically accept parameter defaults when no value is provided.
+
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_delete_--help.golden

@@ -18,7 +18,7 @@ OPTIONS:
           resources.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_dotfiles_--help.golden

@@ -24,7 +24,7 @@ OPTIONS:
           empty, will use $HOME.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_logout_--help.golden

@@ -7,7 +7,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_create_--help.golden

@@ -7,7 +7,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_roles_create_--help.golden

@@ -18,7 +18,7 @@ OPTIONS:
           Reads stdin for the json role definition to upload.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_roles_update_--help.golden

@@ -23,7 +23,7 @@ OPTIONS:
           Reads stdin for the json role definition to upload.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_settings_set_--help.golden

@@ -15,6 +15,7 @@ SUBCOMMANDS:
                          memberships from an IdP.
     role-sync            Role sync settings to sync organization roles from an
                          IdP.
+    workspace-sharing    Workspace sharing settings for the organization.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_settings_set_--help_--help.golden

@@ -15,6 +15,7 @@ SUBCOMMANDS:
                          memberships from an IdP.
     role-sync            Role sync settings to sync organization roles from an
                          IdP.
+    workspace-sharing    Workspace sharing settings for the organization.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_settings_show_--help.golden

@@ -15,6 +15,7 @@ SUBCOMMANDS:
                          memberships from an IdP.
     role-sync            Role sync settings to sync organization roles from an
                          IdP.
+    workspace-sharing    Workspace sharing settings for the organization.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_organizations_settings_show_--help_--help.golden

@@ -15,6 +15,7 @@ SUBCOMMANDS:
                          memberships from an IdP.
     role-sync            Role sync settings to sync organization roles from an
                          IdP.
+    workspace-sharing    Workspace sharing settings for the organization.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_publickey_--help.golden

@@ -13,7 +13,7 @@ OPTIONS:
           services it's registered with.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_rename_--help.golden

@@ -7,7 +7,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_restart_--help.golden

@@ -39,7 +39,7 @@ OPTIONS:
           pairs for the parameters.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_server_--help.golden

@@ -121,6 +121,10 @@ AI BRIDGE OPTIONS:
           See
           https://docs.claude.com/en/docs/claude-code/settings#environment-variables.
 
+      --aibridge-circuit-breaker-enabled bool, $CODER_AIBRIDGE_CIRCUIT_BREAKER_ENABLED (default: false)
+          Enable the circuit breaker to protect against cascading failures from
+          upstream AI provider rate limits (429, 503, 529 overloaded).
+
       --aibridge-retention duration, $CODER_AIBRIDGE_RETENTION (default: 60d)
           Length of time to retain data such as interceptions and all related
           records (token, prompt, tool use).
@@ -147,6 +151,10 @@ AI BRIDGE OPTIONS:
           Maximum number of AI Bridge requests per second per replica. Set to 0
           to disable (unlimited).
 
+      --aibridge-structured-logging bool, $CODER_AIBRIDGE_STRUCTURED_LOGGING (default: false)
+          Emit structured logs for AI Bridge interception records. Use this for
+          exporting these records to external SIEM or observability systems.
+
 AI BRIDGE PROXY OPTIONS: 
       --aibridge-proxy-cert-file string, $CODER_AIBRIDGE_PROXY_CERT_FILE
           Path to the CA certificate file for AI Bridge Proxy.
@@ -161,6 +169,17 @@ AI BRIDGE PROXY OPTIONS:
       --aibridge-proxy-listen-addr string, $CODER_AIBRIDGE_PROXY_LISTEN_ADDR (default: :8888)
           The address the AI Bridge Proxy will listen on.
 
+      --aibridge-proxy-upstream string, $CODER_AIBRIDGE_PROXY_UPSTREAM
+          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.
+
+      --aibridge-proxy-upstream-ca string, $CODER_AIBRIDGE_PROXY_UPSTREAM_CA
+          Path to a PEM-encoded CA certificate to trust for the upstream proxy's
+          TLS connection. Only needed for HTTPS upstream proxies with
+          certificates not trusted by the system. If not provided, the system
+          certificate pool is used.
+
 CLIENT OPTIONS: 
 These options change the behavior of how clients interact with the Coder.
 Clients include the Coder CLI, Coder Desktop, IDE extensions, and the web UI.

cli/testdata/coder_start_--help.golden

@@ -42,7 +42,7 @@ OPTIONS:
           pairs for the parameters.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_stop_--help.golden

@@ -7,7 +7,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_support_bundle_--help.golden

@@ -14,12 +14,25 @@ OPTIONS:
           File path for writing the generated support bundle. Defaults to
           coder-support-$(date +%s).zip.
 
+      --pprof bool, $CODER_SUPPORT_BUNDLE_PPROF
+          Collect pprof profiling data from the Coder server and agent. Requires
+          Coder server version 2.28.0 or newer.
+
+      --template string, $CODER_SUPPORT_BUNDLE_TEMPLATE
+          Template name to include in the support bundle. Use
+          org_name/template_name if template name is reused across multiple
+          organizations.
+
       --url-override string, $CODER_SUPPORT_BUNDLE_URL_OVERRIDE
           Override the URL to your Coder deployment. This may be useful, for
           example, if you need to troubleshoot a specific Coder replica.
 
+      --workspaces-total-cap int, $CODER_SUPPORT_BUNDLE_WORKSPACES_TOTAL_CAP
+          Maximum number of workspaces to include in the support bundle. Set to
+          0 or negative value to disable the cap. Defaults to 10.
+
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_task_delete_--help.golden

@@ -21,7 +21,7 @@ USAGE:
 
 OPTIONS:
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_archive_--help.golden

@@ -14,7 +14,7 @@ OPTIONS:
           versions are archived.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_create_--help.golden

@@ -68,7 +68,7 @@ OPTIONS:
           Specify a file path with values for Terraform-managed variables.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_delete_--help.golden

@@ -12,7 +12,7 @@ OPTIONS:
           Select which organization (uuid or name) to use.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_edit_--help.golden

@@ -91,7 +91,7 @@ OPTIONS:
           for more details.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_pull_--help.golden

@@ -18,7 +18,7 @@ OPTIONS:
           the template version to pull.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
       --zip bool
           Output the template as a zip archive to stdout.

cli/testdata/coder_templates_push_--help.golden

@@ -48,7 +48,7 @@ OPTIONS:
           Specify a file path with values for Terraform-managed variables.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_versions_archive_--help.golden

@@ -11,7 +11,7 @@ OPTIONS:
           Select which organization (uuid or name) to use.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_templates_versions_unarchive_--help.golden

@@ -11,7 +11,7 @@ OPTIONS:
           Select which organization (uuid or name) to use.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/coder_users_edit-roles_--help.golden

@@ -11,7 +11,7 @@ OPTIONS:
           the user may have.
 
   -y, --yes bool
-          Bypass prompts.
+          Bypass confirmation prompts.
 
 ———
 Run `coder --help` for a list of global options.

cli/testdata/server-config.yaml.golden

@@ -773,6 +773,27 @@ aibridge:
   # (unlimited).
   # (default: 0, type: int)
   rateLimit: 0
+  # Emit structured logs for AI Bridge interception records. Use this for exporting
+  # these records to external SIEM or observability systems.
+  # (default: false, type: bool)
+  structuredLogging: false
+  # Enable the circuit breaker to protect against cascading failures from upstream
+  # AI provider rate limits (429, 503, 529 overloaded).
+  # (default: false, type: bool)
+  circuitBreakerEnabled: false
+  # Number of consecutive failures that triggers the circuit breaker to open.
+  # (default: 5, type: int)
+  circuitBreakerFailureThreshold: 5
+  # Cyclic period of the closed state for clearing internal failure counts.
+  # (default: 10s, type: duration)
+  circuitBreakerInterval: 10s
+  # How long the circuit breaker stays open before transitioning to half-open state.
+  # (default: 30s, type: duration)
+  circuitBreakerTimeout: 30s
+  # Maximum number of requests allowed in half-open state before deciding to close
+  # or re-open the circuit.
+  # (default: 3, type: int)
+  circuitBreakerMaxRequests: 3
 aibridgeproxy:
   # Enable the AI Bridge MITM Proxy for intercepting and decrypting AI provider
   # requests.
@@ -794,6 +815,15 @@ aibridgeproxy:
   domain_allowlist:
     - api.anthropic.com
     - api.openai.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)
+  upstream_proxy: ""
+  # Path to a PEM-encoded CA certificate to trust for the upstream proxy's TLS
+  # connection. Only needed for HTTPS upstream proxies with certificates not trusted
+  # by the system. If not provided, the system certificate pool is used.
+  # (default: <unset>, type: string)
+  upstream_proxy_ca: ""
 # Configure data retention policies for various database tables. Retention
 # policies automatically purge old data to reduce database size and improve
 # performance. Setting a retention duration to 0 disables automatic purging for

coderd/agentapi/api.go

@@ -25,6 +25,7 @@ import (
 	"github.com/coder/coder/v2/coderd/externalauth"
 	"github.com/coder/coder/v2/coderd/notifications"
 	"github.com/coder/coder/v2/coderd/prometheusmetrics"
+	"github.com/coder/coder/v2/coderd/telemetry"
 	"github.com/coder/coder/v2/coderd/tracing"
 	"github.com/coder/coder/v2/coderd/workspacestats"
 	"github.com/coder/coder/v2/coderd/wspubsub"
@@ -68,6 +69,7 @@ type Options struct {
 	AgentID        uuid.UUID
 	OwnerID        uuid.UUID
 	WorkspaceID    uuid.UUID
+	TemplateID     uuid.UUID
 	OrganizationID uuid.UUID
 
 	AuthenticatedCtx                  context.Context
@@ -84,6 +86,7 @@ type Options struct {
 	PublishWorkspaceUpdateFn          func(ctx context.Context, userID uuid.UUID, event wspubsub.WorkspaceEvent)
 	PublishWorkspaceAgentLogsUpdateFn func(ctx context.Context, workspaceAgentID uuid.UUID, msg agentsdk.LogsNotifyMessage)
 	NetworkTelemetryHandler           func(batch []*tailnetproto.TelemetryEvent)
+	BoundaryTelemetryCollector        *telemetry.BoundaryTelemetryCollector
 
 	AccessURL                 *url.URL
 	AppHostname               string
@@ -221,8 +224,11 @@ func New(opts Options, workspace database.Workspace) *API {
 	}
 
 	api.BoundaryLogsAPI = &BoundaryLogsAPI{
-		Log:         opts.Log,
-		WorkspaceID: opts.WorkspaceID,
+		Log:                        opts.Log,
+		OwnerID:                    opts.OwnerID,
+		WorkspaceID:                opts.WorkspaceID,
+		TemplateID:                 opts.TemplateID,
+		BoundaryTelemetryCollector: opts.BoundaryTelemetryCollector,
 	}
 
 	// Start background cache refresh loop to handle workspace changes

coderd/agentapi/boundary_logs.go

@@ -8,14 +8,23 @@ import (
 
 	"cdr.dev/slog/v3"
 	agentproto "github.com/coder/coder/v2/agent/proto"
+	"github.com/coder/coder/v2/coderd/telemetry"
 )
 
 type BoundaryLogsAPI struct {
-	Log         slog.Logger
-	WorkspaceID uuid.UUID
+	Log                        slog.Logger
+	OwnerID                    uuid.UUID
+	WorkspaceID                uuid.UUID
+	TemplateID                 uuid.UUID
+	BoundaryTelemetryCollector *telemetry.BoundaryTelemetryCollector
 }
 
 func (a *BoundaryLogsAPI) ReportBoundaryLogs(ctx context.Context, req *agentproto.ReportBoundaryLogsRequest) (*agentproto.ReportBoundaryLogsResponse, error) {
+	// Record boundary usage for telemetry if we have any logs.
+	if len(req.Logs) > 0 && a.BoundaryTelemetryCollector != nil {
+		a.BoundaryTelemetryCollector.RecordBoundaryUsage(a.OwnerID, a.WorkspaceID, a.TemplateID)
+	}
+
 	for _, l := range req.Logs {
 		var logTime time.Time
 		if l.Time != nil {

coderd/apidoc/docs.go

@@ -2628,7 +2628,8 @@ const docTemplate = `{
                     },
                     {
                         "enum": [
-                            "code"
+                            "code",
+                            "token"
                         ],
                         "type": "string",
                         "description": "Response type",
@@ -2683,7 +2684,8 @@ const docTemplate = `{
                     },
                     {
                         "enum": [
-                            "code"
+                            "code",
+                            "token"
                         ],
                         "type": "string",
                         "description": "Response type",
@@ -2914,7 +2916,10 @@ const docTemplate = `{
                     {
                         "enum": [
                             "authorization_code",
-                            "refresh_token"
+                            "refresh_token",
+                            "password",
+                            "client_credentials",
+                            "implicit"
                         ],
                         "type": "string",
                         "description": "Grant type",
@@ -4566,6 +4571,86 @@ const docTemplate = `{
                 }
             }
         },
+        "/organizations/{organization}/settings/workspace-sharing": {
+            "get": {
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Enterprise"
+                ],
+                "summary": "Get workspace sharing settings for organization",
+                "operationId": "get-workspace-sharing-settings-for-organization",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "format": "uuid",
+                        "description": "Organization ID",
+                        "name": "organization",
+                        "in": "path",
+                        "required": true
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+                        }
+                    }
+                }
+            },
+            "patch": {
+                "security": [
+                    {
+                        "CoderSessionToken": []
+                    }
+                ],
+                "consumes": [
+                    "application/json"
+                ],
+                "produces": [
+                    "application/json"
+                ],
+                "tags": [
+                    "Enterprise"
+                ],
+                "summary": "Update workspace sharing settings for organization",
+                "operationId": "update-workspace-sharing-settings-for-organization",
+                "parameters": [
+                    {
+                        "type": "string",
+                        "format": "uuid",
+                        "description": "Organization ID",
+                        "name": "organization",
+                        "in": "path",
+                        "required": true
+                    },
+                    {
+                        "description": "Workspace sharing settings",
+                        "name": "request",
+                        "in": "body",
+                        "required": true,
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+                        }
+                    }
+                ],
+                "responses": {
+                    "200": {
+                        "description": "OK",
+                        "schema": {
+                            "$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+                        }
+                    }
+                }
+            }
+        },
         "/organizations/{organization}/templates": {
             "get": {
                 "security": [
@@ -11953,6 +12038,22 @@ const docTemplate = `{
                 "bedrock": {
                     "$ref": "#/definitions/codersdk.AIBridgeBedrockConfig"
                 },
+                "circuit_breaker_enabled": {
+                    "description": "Circuit breaker protects against cascading failures from upstream AI\nprovider rate limits (429, 503, 529 overloaded).",
+                    "type": "boolean"
+                },
+                "circuit_breaker_failure_threshold": {
+                    "type": "integer"
+                },
+                "circuit_breaker_interval": {
+                    "type": "integer"
+                },
+                "circuit_breaker_max_requests": {
+                    "type": "integer"
+                },
+                "circuit_breaker_timeout": {
+                    "type": "integer"
+                },
                 "enabled": {
                     "type": "boolean"
                 },
@@ -11970,6 +12071,9 @@ const docTemplate = `{
                 },
                 "retention": {
                     "type": "integer"
+                },
+                "structured_logging": {
+                    "type": "boolean"
                 }
             }
         },
@@ -12069,6 +12173,12 @@ const docTemplate = `{
                 },
                 "listen_addr": {
                     "type": "string"
+                },
+                "upstream_proxy": {
+                    "type": "string"
+                },
+                "upstream_proxy_ca": {
+                    "type": "string"
                 }
             }
         },
@@ -15761,13 +15871,13 @@ const docTemplate = `{
                 "code_challenge_methods_supported": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2PKCECodeChallengeMethod"
                     }
                 },
                 "grant_types_supported": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
                     }
                 },
                 "issuer": {
@@ -15779,7 +15889,7 @@ const docTemplate = `{
                 "response_types_supported": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
                     }
                 },
                 "revocation_endpoint": {
@@ -15797,7 +15907,7 @@ const docTemplate = `{
                 "token_endpoint_auth_methods_supported": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
                     }
                 }
             }
@@ -15829,7 +15939,7 @@ const docTemplate = `{
                 "grant_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
                     }
                 },
                 "jwks": {
@@ -15851,10 +15961,7 @@ const docTemplate = `{
                     }
                 },
                 "registration_access_token": {
-                    "type": "array",
-                    "items": {
-                        "type": "integer"
-                    }
+                    "type": "string"
                 },
                 "registration_client_uri": {
                     "type": "string"
@@ -15862,7 +15969,7 @@ const docTemplate = `{
                 "response_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
                     }
                 },
                 "scope": {
@@ -15875,7 +15982,7 @@ const docTemplate = `{
                     "type": "string"
                 },
                 "token_endpoint_auth_method": {
-                    "type": "string"
+                    "$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
                 },
                 "tos_uri": {
                     "type": "string"
@@ -15900,7 +16007,7 @@ const docTemplate = `{
                 "grant_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
                     }
                 },
                 "jwks": {
@@ -15924,7 +16031,7 @@ const docTemplate = `{
                 "response_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
                     }
                 },
                 "scope": {
@@ -15940,7 +16047,7 @@ const docTemplate = `{
                     "type": "string"
                 },
                 "token_endpoint_auth_method": {
-                    "type": "string"
+                    "$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
                 },
                 "tos_uri": {
                     "type": "string"
@@ -15977,7 +16084,7 @@ const docTemplate = `{
                 "grant_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
                     }
                 },
                 "jwks": {
@@ -16007,7 +16114,7 @@ const docTemplate = `{
                 "response_types": {
                     "type": "array",
                     "items": {
-                        "type": "string"
+                        "$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
                     }
                 },
                 "scope": {
@@ -16020,7 +16127,7 @@ const docTemplate = `{
                     "type": "string"
                 },
                 "token_endpoint_auth_method": {
-                    "type": "string"
+                    "$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
                 },
                 "tos_uri": {
                     "type": "string"
@@ -16073,6 +16180,17 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.OAuth2PKCECodeChallengeMethod": {
+            "type": "string",
+            "enum": [
+                "S256",
+                "plain"
+            ],
+            "x-enum-varnames": [
+                "OAuth2PKCECodeChallengeMethodS256",
+                "OAuth2PKCECodeChallengeMethodPlain"
+            ]
+        },
         "codersdk.OAuth2ProtectedResourceMetadata": {
             "type": "object",
             "properties": {
@@ -16152,6 +16270,47 @@ const docTemplate = `{
                 }
             }
         },
+        "codersdk.OAuth2ProviderGrantType": {
+            "type": "string",
+            "enum": [
+                "authorization_code",
+                "refresh_token",
+                "password",
+                "client_credentials",
+                "implicit"
+            ],
+            "x-enum-varnames": [
+                "OAuth2ProviderGrantTypeAuthorizationCode",
+                "OAuth2ProviderGrantTypeRefreshToken",
+                "OAuth2ProviderGrantTypePassword",
+                "OAuth2ProviderGrantTypeClientCredentials",
+                "OAuth2ProviderGrantTypeImplicit"
+            ]
+        },
+        "codersdk.OAuth2ProviderResponseType": {
+            "type": "string",
+            "enum": [
+                "code",
+                "token"
+            ],
+            "x-enum-varnames": [
+                "OAuth2ProviderResponseTypeCode",
+                "OAuth2ProviderResponseTypeToken"
+            ]
+        },
+        "codersdk.OAuth2TokenEndpointAuthMethod": {
+            "type": "string",
+            "enum": [
+                "client_secret_basic",
+                "client_secret_post",
+                "none"
+            ],
+            "x-enum-varnames": [
+                "OAuth2TokenEndpointAuthMethodClientSecretBasic",
+                "OAuth2TokenEndpointAuthMethodClientSecretPost",
+                "OAuth2TokenEndpointAuthMethodNone"
+            ]
+        },
         "codersdk.OAuthConversionResponse": {
             "type": "object",
             "properties": {
@@ -21451,6 +21610,14 @@ const docTemplate = `{
                 "WorkspaceRoleDeleted"
             ]
         },
+        "codersdk.WorkspaceSharingSettings": {
+            "type": "object",
+            "properties": {
+                "sharing_disabled": {
+                    "type": "boolean"
+                }
+            }
+        },
         "codersdk.WorkspaceStatus": {
             "type": "string",
             "enum": [

coderd/apidoc/swagger.json

@@ -2304,7 +2304,7 @@
 						"required": true
 					},
 					{
-						"enum": ["code"],
+						"enum": ["code", "token"],
 						"type": "string",
 						"description": "Response type",
 						"name": "response_type",
@@ -2355,7 +2355,7 @@
 						"required": true
 					},
 					{
-						"enum": ["code"],
+						"enum": ["code", "token"],
 						"type": "string",
 						"description": "Response type",
 						"name": "response_type",
@@ -2555,7 +2555,13 @@
 						"in": "formData"
 					},
 					{
-						"enum": ["authorization_code", "refresh_token"],
+						"enum": [
+							"authorization_code",
+							"refresh_token",
+							"password",
+							"client_credentials",
+							"implicit"
+						],
 						"type": "string",
 						"description": "Grant type",
 						"name": "grant_type",
@@ -4036,6 +4042,76 @@
 				}
 			}
 		},
+		"/organizations/{organization}/settings/workspace-sharing": {
+			"get": {
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"produces": ["application/json"],
+				"tags": ["Enterprise"],
+				"summary": "Get workspace sharing settings for organization",
+				"operationId": "get-workspace-sharing-settings-for-organization",
+				"parameters": [
+					{
+						"type": "string",
+						"format": "uuid",
+						"description": "Organization ID",
+						"name": "organization",
+						"in": "path",
+						"required": true
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+						}
+					}
+				}
+			},
+			"patch": {
+				"security": [
+					{
+						"CoderSessionToken": []
+					}
+				],
+				"consumes": ["application/json"],
+				"produces": ["application/json"],
+				"tags": ["Enterprise"],
+				"summary": "Update workspace sharing settings for organization",
+				"operationId": "update-workspace-sharing-settings-for-organization",
+				"parameters": [
+					{
+						"type": "string",
+						"format": "uuid",
+						"description": "Organization ID",
+						"name": "organization",
+						"in": "path",
+						"required": true
+					},
+					{
+						"description": "Workspace sharing settings",
+						"name": "request",
+						"in": "body",
+						"required": true,
+						"schema": {
+							"$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+						}
+					}
+				],
+				"responses": {
+					"200": {
+						"description": "OK",
+						"schema": {
+							"$ref": "#/definitions/codersdk.WorkspaceSharingSettings"
+						}
+					}
+				}
+			}
+		},
 		"/organizations/{organization}/templates": {
 			"get": {
 				"security": [
@@ -10614,6 +10690,22 @@
 				"bedrock": {
 					"$ref": "#/definitions/codersdk.AIBridgeBedrockConfig"
 				},
+				"circuit_breaker_enabled": {
+					"description": "Circuit breaker protects against cascading failures from upstream AI\nprovider rate limits (429, 503, 529 overloaded).",
+					"type": "boolean"
+				},
+				"circuit_breaker_failure_threshold": {
+					"type": "integer"
+				},
+				"circuit_breaker_interval": {
+					"type": "integer"
+				},
+				"circuit_breaker_max_requests": {
+					"type": "integer"
+				},
+				"circuit_breaker_timeout": {
+					"type": "integer"
+				},
 				"enabled": {
 					"type": "boolean"
 				},
@@ -10631,6 +10723,9 @@
 				},
 				"retention": {
 					"type": "integer"
+				},
+				"structured_logging": {
+					"type": "boolean"
 				}
 			}
 		},
@@ -10730,6 +10825,12 @@
 				},
 				"listen_addr": {
 					"type": "string"
+				},
+				"upstream_proxy": {
+					"type": "string"
+				},
+				"upstream_proxy_ca": {
+					"type": "string"
 				}
 			}
 		},
@@ -14280,13 +14381,13 @@
 				"code_challenge_methods_supported": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2PKCECodeChallengeMethod"
 					}
 				},
 				"grant_types_supported": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
 					}
 				},
 				"issuer": {
@@ -14298,7 +14399,7 @@
 				"response_types_supported": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
 					}
 				},
 				"revocation_endpoint": {
@@ -14316,7 +14417,7 @@
 				"token_endpoint_auth_methods_supported": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
 					}
 				}
 			}
@@ -14348,7 +14449,7 @@
 				"grant_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
 					}
 				},
 				"jwks": {
@@ -14370,10 +14471,7 @@
 					}
 				},
 				"registration_access_token": {
-					"type": "array",
-					"items": {
-						"type": "integer"
-					}
+					"type": "string"
 				},
 				"registration_client_uri": {
 					"type": "string"
@@ -14381,7 +14479,7 @@
 				"response_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
 					}
 				},
 				"scope": {
@@ -14394,7 +14492,7 @@
 					"type": "string"
 				},
 				"token_endpoint_auth_method": {
-					"type": "string"
+					"$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
 				},
 				"tos_uri": {
 					"type": "string"
@@ -14419,7 +14517,7 @@
 				"grant_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
 					}
 				},
 				"jwks": {
@@ -14443,7 +14541,7 @@
 				"response_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
 					}
 				},
 				"scope": {
@@ -14459,7 +14557,7 @@
 					"type": "string"
 				},
 				"token_endpoint_auth_method": {
-					"type": "string"
+					"$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
 				},
 				"tos_uri": {
 					"type": "string"
@@ -14496,7 +14594,7 @@
 				"grant_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderGrantType"
 					}
 				},
 				"jwks": {
@@ -14526,7 +14624,7 @@
 				"response_types": {
 					"type": "array",
 					"items": {
-						"type": "string"
+						"$ref": "#/definitions/codersdk.OAuth2ProviderResponseType"
 					}
 				},
 				"scope": {
@@ -14539,7 +14637,7 @@
 					"type": "string"
 				},
 				"token_endpoint_auth_method": {
-					"type": "string"
+					"$ref": "#/definitions/codersdk.OAuth2TokenEndpointAuthMethod"
 				},
 				"tos_uri": {
 					"type": "string"
@@ -14592,6 +14690,14 @@
 				}
 			}
 		},
+		"codersdk.OAuth2PKCECodeChallengeMethod": {
+			"type": "string",
+			"enum": ["S256", "plain"],
+			"x-enum-varnames": [
+				"OAuth2PKCECodeChallengeMethodS256",
+				"OAuth2PKCECodeChallengeMethodPlain"
+			]
+		},
 		"codersdk.OAuth2ProtectedResourceMetadata": {
 			"type": "object",
 			"properties": {
@@ -14671,6 +14777,40 @@
 				}
 			}
 		},
+		"codersdk.OAuth2ProviderGrantType": {
+			"type": "string",
+			"enum": [
+				"authorization_code",
+				"refresh_token",
+				"password",
+				"client_credentials",
+				"implicit"
+			],
+			"x-enum-varnames": [
+				"OAuth2ProviderGrantTypeAuthorizationCode",
+				"OAuth2ProviderGrantTypeRefreshToken",
+				"OAuth2ProviderGrantTypePassword",
+				"OAuth2ProviderGrantTypeClientCredentials",
+				"OAuth2ProviderGrantTypeImplicit"
+			]
+		},
+		"codersdk.OAuth2ProviderResponseType": {
+			"type": "string",
+			"enum": ["code", "token"],
+			"x-enum-varnames": [
+				"OAuth2ProviderResponseTypeCode",
+				"OAuth2ProviderResponseTypeToken"
+			]
+		},
+		"codersdk.OAuth2TokenEndpointAuthMethod": {
+			"type": "string",
+			"enum": ["client_secret_basic", "client_secret_post", "none"],
+			"x-enum-varnames": [
+				"OAuth2TokenEndpointAuthMethodClientSecretBasic",
+				"OAuth2TokenEndpointAuthMethodClientSecretPost",
+				"OAuth2TokenEndpointAuthMethodNone"
+			]
+		},
 		"codersdk.OAuthConversionResponse": {
 			"type": "object",
 			"properties": {
@@ -19730,6 +19870,14 @@
 				"WorkspaceRoleDeleted"
 			]
 		},
+		"codersdk.WorkspaceSharingSettings": {
+			"type": "object",
+			"properties": {
+				"sharing_disabled": {
+					"type": "boolean"
+				}
+			}
+		},
 		"codersdk.WorkspaceStatus": {
 			"type": "string",
 			"enum": [

coderd/coderd.go

@@ -27,6 +27,7 @@ import (
 	"github.com/google/uuid"
 	"github.com/klauspost/compress/zstd"
 	"github.com/prometheus/client_golang/prometheus"
+	"github.com/prometheus/client_golang/prometheus/collectors"
 	"github.com/prometheus/client_golang/prometheus/promhttp"
 	httpSwagger "github.com/swaggo/http-swagger/v2"
 	"go.opentelemetry.io/otel/trace"
@@ -196,6 +197,7 @@ type Options struct {
 	DERPMapUpdateFrequency         time.Duration
 	NetworkTelemetryBatchFrequency time.Duration
 	NetworkTelemetryBatchMaxSize   int
+	BoundaryTelemetryCollector     *telemetry.BoundaryTelemetryCollector
 	SwaggerEndpoint                bool
 	TemplateScheduleStore          *atomic.Pointer[schedule.TemplateScheduleStore]
 	UserQuietHoursScheduleStore    *atomic.Pointer[schedule.UserQuietHoursScheduleStore]
@@ -205,7 +207,7 @@ type Options struct {
 	// tokens issued by and passed to the coordinator DRPC API.
 	CoordinatorResumeTokenProvider tailnet.ResumeTokenProvider
 
-	HealthcheckFunc              func(ctx context.Context, apiKey string) *healthsdk.HealthcheckReport
+	HealthcheckFunc              func(ctx context.Context, apiKey string, progress *healthcheck.Progress) *healthsdk.HealthcheckReport
 	HealthcheckTimeout           time.Duration
 	HealthcheckRefresh           time.Duration
 	WorkspaceProxiesFetchUpdater *atomic.Pointer[healthcheck.WorkspaceProxiesFetchUpdater]
@@ -334,6 +336,7 @@ func New(options *Options) *API {
 
 	if options.PrometheusRegistry == nil {
 		options.PrometheusRegistry = prometheus.NewRegistry()
+		options.PrometheusRegistry.MustRegister(collectors.NewGoCollector())
 	}
 	if options.Authorizer == nil {
 		options.Authorizer = rbac.NewCachingAuthorizer(options.PrometheusRegistry)
@@ -681,7 +684,7 @@ func New(options *Options) *API {
 	}
 
 	if options.HealthcheckFunc == nil {
-		options.HealthcheckFunc = func(ctx context.Context, apiKey string) *healthsdk.HealthcheckReport {
+		options.HealthcheckFunc = func(ctx context.Context, apiKey string, progress *healthcheck.Progress) *healthsdk.HealthcheckReport {
 			// NOTE: dismissed healthchecks are marked in formatHealthcheck.
 			// Not here, as this result gets cached.
 			return healthcheck.Run(ctx, &healthcheck.ReportOptions{
@@ -709,6 +712,7 @@ func New(options *Options) *API {
 					StaleInterval:          provisionerdserver.StaleInterval,
 					// TimeNow set to default, see healthcheck/provisioner.go
 				},
+				Progress: progress,
 			})
 		}
 	}
@@ -881,6 +885,7 @@ func New(options *Options) *API {
 		loggermw.Logger(api.Logger),
 		singleSlashMW,
 		rolestore.CustomRoleMW,
+		httpmw.HTTPRoute, // NB: prometheusMW depends on this middleware.
 		prometheusMW,
 		// Build-Version is helpful for debugging.
 		func(next http.Handler) http.Handler {
@@ -1434,9 +1439,7 @@ func New(options *Options) *API {
 						Optional: true,
 					}),
 					httpmw.RequireAPIKeyOrWorkspaceProxyAuth(),
-
-					httpmw.ExtractWorkspaceAgentParam(options.Database),
-					httpmw.ExtractWorkspaceParam(options.Database),
+					httpmw.ExtractWorkspaceAgentAndWorkspaceParam(options.Database),
 				)
 				r.Get("/", api.workspaceAgent)
 				r.Get("/watch-metadata", api.watchWorkspaceAgentMetadataSSE)
@@ -1859,8 +1862,9 @@ type API struct {
 	// This is used to gate features that are not yet ready for production.
 	Experiments codersdk.Experiments
 
-	healthCheckGroup *singleflight.Group[string, *healthsdk.HealthcheckReport]
-	healthCheckCache atomic.Pointer[healthsdk.HealthcheckReport]
+	healthCheckGroup    *singleflight.Group[string, *healthsdk.HealthcheckReport]
+	healthCheckCache    atomic.Pointer[healthsdk.HealthcheckReport]
+	healthCheckProgress healthcheck.Progress
 
 	statsReporter *workspacestats.Reporter
 

coderd/coderdtest/coderdtest.go

@@ -69,6 +69,7 @@ import (
 	"github.com/coder/coder/v2/coderd/externalauth"
 	"github.com/coder/coder/v2/coderd/files"
 	"github.com/coder/coder/v2/coderd/gitsshkey"
+	"github.com/coder/coder/v2/coderd/healthcheck"
 	"github.com/coder/coder/v2/coderd/httpmw"
 	"github.com/coder/coder/v2/coderd/jobreaper"
 	"github.com/coder/coder/v2/coderd/notifications"
@@ -131,7 +132,7 @@ type Options struct {
 	CoordinatorResumeTokenProvider tailnet.ResumeTokenProvider
 	ConnectionLogger               connectionlog.ConnectionLogger
 
-	HealthcheckFunc    func(ctx context.Context, apiKey string) *healthsdk.HealthcheckReport
+	HealthcheckFunc    func(ctx context.Context, apiKey string, progress *healthcheck.Progress) *healthsdk.HealthcheckReport
 	HealthcheckTimeout time.Duration
 	HealthcheckRefresh time.Duration
 

coderd/database/db2sdk/db2sdk.go

@@ -569,7 +569,7 @@ func AppSubdomain(dbApp database.WorkspaceApp, agentName, workspaceName, ownerNa
 	}.String()
 }
 
-func Apps(dbApps []database.WorkspaceApp, statuses []database.WorkspaceAppStatus, agent database.WorkspaceAgent, ownerName string, workspace database.Workspace) []codersdk.WorkspaceApp {
+func Apps(dbApps []database.WorkspaceApp, statuses []database.WorkspaceAppStatus, agent database.WorkspaceAgent, ownerName string, workspace database.WorkspaceTable) []codersdk.WorkspaceApp {
 	sort.Slice(dbApps, func(i, j int) bool {
 		if dbApps[i].DisplayOrder != dbApps[j].DisplayOrder {
 			return dbApps[i].DisplayOrder < dbApps[j].DisplayOrder

coderd/database/dbauthz/dbauthz.go

@@ -1663,6 +1663,20 @@ func (q *querier) DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, u
 	return q.db.DeleteApplicationConnectAPIKeysByUserID(ctx, userID)
 }
 
+func (q *querier) DeleteBoundaryActiveUsersBefore(ctx context.Context, recordedAt time.Time) error {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return err
+	}
+	return q.db.DeleteBoundaryActiveUsersBefore(ctx, recordedAt)
+}
+
+func (q *querier) DeleteBoundaryActiveWorkspacesBefore(ctx context.Context, recordedAt time.Time) error {
+	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceSystem); err != nil {
+		return err
+	}
+	return q.db.DeleteBoundaryActiveWorkspacesBefore(ctx, recordedAt)
+}
+
 func (q *querier) DeleteCoordinator(ctx context.Context, id uuid.UUID) error {
 	if err := q.authorizeContext(ctx, policy.ActionDelete, rbac.ResourceTailnetCoordinator); err != nil {
 		return err
@@ -1965,6 +1979,14 @@ func (q *querier) DeleteWorkspaceACLByID(ctx context.Context, id uuid.UUID) erro
 	return fetchAndExec(q.log, q.auth, policy.ActionShare, fetch, q.db.DeleteWorkspaceACLByID)(ctx, id)
 }
 
+func (q *querier) DeleteWorkspaceACLsByOrganization(ctx context.Context, organizationID uuid.UUID) error {
+	// This is a system-only function.
+	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourceSystem); err != nil {
+		return err
+	}
+	return q.db.DeleteWorkspaceACLsByOrganization(ctx, organizationID)
+}
+
 func (q *querier) DeleteWorkspaceAgentPortShare(ctx context.Context, arg database.DeleteWorkspaceAgentPortShareParams) error {
 	w, err := q.db.GetWorkspaceByID(ctx, arg.WorkspaceID)
 	if err != nil {
@@ -2243,6 +2265,20 @@ func (q *querier) GetAuthorizationUserRoles(ctx context.Context, userID uuid.UUI
 	return q.db.GetAuthorizationUserRoles(ctx, userID)
 }
 
+func (q *querier) GetBoundaryActiveUsersSince(ctx context.Context, recordedAt time.Time) ([]uuid.UUID, error) {
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetBoundaryActiveUsersSince(ctx, recordedAt)
+}
+
+func (q *querier) GetBoundaryActiveWorkspacesSince(ctx context.Context, recordedAt time.Time) ([]database.GetBoundaryActiveWorkspacesSinceRow, error) {
+	if err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceSystem); err != nil {
+		return nil, err
+	}
+	return q.db.GetBoundaryActiveWorkspacesSince(ctx, recordedAt)
+}
+
 func (q *querier) GetConnectionLogsOffset(ctx context.Context, arg database.GetConnectionLogsOffsetParams) ([]database.GetConnectionLogsOffsetRow, error) {
 	// Just like with the audit logs query, shortcut if the user is an owner.
 	err := q.authorizeContext(ctx, policy.ActionRead, rbac.ResourceConnectionLog)
@@ -3592,7 +3628,7 @@ func (q *querier) GetWorkspaceACLByID(ctx context.Context, id uuid.UUID) (databa
 	if err != nil {
 		return database.GetWorkspaceACLByIDRow{}, err
 	}
-	if err := q.authorizeContext(ctx, policy.ActionShare, workspace); err != nil {
+	if err := q.authorizeContext(ctx, policy.ActionRead, workspace); err != nil {
 		return database.GetWorkspaceACLByIDRow{}, err
 	}
 	return q.db.GetWorkspaceACLByID(ctx, id)
@@ -3606,6 +3642,10 @@ func (q *querier) GetWorkspaceAgentAndLatestBuildByAuthToken(ctx context.Context
 	return q.db.GetWorkspaceAgentAndLatestBuildByAuthToken(ctx, authToken)
 }
 
+func (q *querier) GetWorkspaceAgentAndWorkspaceByID(ctx context.Context, id uuid.UUID) (database.GetWorkspaceAgentAndWorkspaceByIDRow, error) {
+	return fetch(q.log, q.auth, q.db.GetWorkspaceAgentAndWorkspaceByID)(ctx, id)
+}
+
 func (q *querier) GetWorkspaceAgentByID(ctx context.Context, id uuid.UUID) (database.WorkspaceAgent, error) {
 	// Fast path: Check if we have a workspace RBAC object in context.
 	// In the agent API this is set at agent connection time to avoid the expensive
@@ -4141,6 +4181,20 @@ func (q *querier) InsertAuditLog(ctx context.Context, arg database.InsertAuditLo
 	return insert(q.log, q.auth, rbac.ResourceAuditLog, q.db.InsertAuditLog)(ctx, arg)
 }
 
+func (q *querier) InsertBoundaryActiveUser(ctx context.Context, arg database.InsertBoundaryActiveUserParams) error {
+	if err := q.authorizeContext(ctx, policy.ActionCreate, rbac.ResourceSystem); err != nil {
+		return err
+	}
+	return q.db.InsertBoundaryActiveUser(ctx, arg)
+}
+
+func (q *querier) InsertBoundaryActiveWorkspace(ctx context.Context, arg database.InsertBoundaryActiveWorkspaceParams) error {
+	if err := q.authorizeContext(ctx, policy.ActionCreate, rbac.ResourceSystem); err != nil {
+		return err
+	}
+	return q.db.InsertBoundaryActiveWorkspace(ctx, arg)
+}
+
 func (q *querier) InsertCryptoKey(ctx context.Context, arg database.InsertCryptoKeyParams) (database.CryptoKey, error) {
 	if err := q.authorizeContext(ctx, policy.ActionCreate, rbac.ResourceCryptoKey); err != nil {
 		return database.CryptoKey{}, err
@@ -5099,6 +5153,13 @@ func (q *querier) UpdateOrganizationDeletedByID(ctx context.Context, arg databas
 	return deleteQ(q.log, q.auth, q.db.GetOrganizationByID, deleteF)(ctx, arg.ID)
 }
 
+func (q *querier) UpdateOrganizationWorkspaceSharingSettings(ctx context.Context, arg database.UpdateOrganizationWorkspaceSharingSettingsParams) (database.Organization, error) {
+	fetch := func(ctx context.Context, arg database.UpdateOrganizationWorkspaceSharingSettingsParams) (database.Organization, error) {
+		return q.db.GetOrganizationByID(ctx, arg.ID)
+	}
+	return updateWithReturn(q.log, q.auth, fetch, q.db.UpdateOrganizationWorkspaceSharingSettings)(ctx, arg)
+}
+
 func (q *querier) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]database.UpdatePrebuildProvisionerJobWithCancelRow, error) {
 	// Prebuild operation for canceling pending prebuild jobs from non-active template versions
 	if err := q.authorizeContext(ctx, policy.ActionUpdate, rbac.ResourcePrebuiltWorkspace); err != nil {

coderd/database/dbauthz/dbauthz_test.go

@@ -880,6 +880,16 @@ func (s *MethodTestSuite) TestOrganization() {
 		dbm.EXPECT().InsertOrganization(gomock.Any(), arg).Return(database.Organization{ID: arg.ID, Name: arg.Name}, nil).AnyTimes()
 		check.Args(arg).Asserts(rbac.ResourceOrganization, policy.ActionCreate)
 	}))
+	s.Run("UpdateOrganizationWorkspaceSharingSettings", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		org := testutil.Fake(s.T(), faker, database.Organization{})
+		arg := database.UpdateOrganizationWorkspaceSharingSettingsParams{
+			ID:                       org.ID,
+			WorkspaceSharingDisabled: true,
+		}
+		dbm.EXPECT().GetOrganizationByID(gomock.Any(), org.ID).Return(org, nil).AnyTimes()
+		dbm.EXPECT().UpdateOrganizationWorkspaceSharingSettings(gomock.Any(), arg).Return(org, nil).AnyTimes()
+		check.Args(arg).Asserts(org, policy.ActionUpdate).Returns(org)
+	}))
 	s.Run("InsertOrganizationMember", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		o := testutil.Fake(s.T(), faker, database.Organization{})
 		u := testutil.Fake(s.T(), faker, database.User{})
@@ -1784,7 +1794,7 @@ func (s *MethodTestSuite) TestWorkspace() {
 		ws := testutil.Fake(s.T(), faker, database.Workspace{})
 		dbM.EXPECT().GetWorkspaceByID(gomock.Any(), ws.ID).Return(ws, nil).AnyTimes()
 		dbM.EXPECT().GetWorkspaceACLByID(gomock.Any(), ws.ID).Return(database.GetWorkspaceACLByIDRow{}, nil).AnyTimes()
-		check.Args(ws.ID).Asserts(ws, policy.ActionShare)
+		check.Args(ws.ID).Asserts(ws, policy.ActionRead)
 	}))
 	s.Run("UpdateWorkspaceACLByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		w := testutil.Fake(s.T(), faker, database.Workspace{})
@@ -1799,6 +1809,11 @@ func (s *MethodTestSuite) TestWorkspace() {
 		dbm.EXPECT().DeleteWorkspaceACLByID(gomock.Any(), w.ID).Return(nil).AnyTimes()
 		check.Args(w.ID).Asserts(w, policy.ActionShare)
 	}))
+	s.Run("DeleteWorkspaceACLsByOrganization", s.Mocked(func(dbm *dbmock.MockStore, _ *gofakeit.Faker, check *expects) {
+		orgID := uuid.New()
+		dbm.EXPECT().DeleteWorkspaceACLsByOrganization(gomock.Any(), orgID).Return(nil).AnyTimes()
+		check.Args(orgID).Asserts(rbac.ResourceSystem, policy.ActionUpdate)
+	}))
 	s.Run("GetLatestWorkspaceBuildByWorkspaceID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		w := testutil.Fake(s.T(), faker, database.Workspace{})
 		b := testutil.Fake(s.T(), faker, database.WorkspaceBuild{WorkspaceID: w.ID})
@@ -1813,6 +1828,11 @@ func (s *MethodTestSuite) TestWorkspace() {
 		dbm.EXPECT().GetWorkspaceAgentByID(gomock.Any(), agt.ID).Return(agt, nil).AnyTimes()
 		check.Args(agt.ID).Asserts(w, policy.ActionRead).Returns(agt)
 	}))
+	s.Run("GetWorkspaceAgentAndWorkspaceByID", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
+		aww := testutil.Fake(s.T(), faker, database.GetWorkspaceAgentAndWorkspaceByIDRow{})
+		dbm.EXPECT().GetWorkspaceAgentAndWorkspaceByID(gomock.Any(), aww.WorkspaceAgent.ID).Return(aww, nil).AnyTimes()
+		check.Args(aww.WorkspaceAgent.ID).Asserts(aww.WorkspaceTable, policy.ActionRead).Returns(aww)
+	}))
 	s.Run("GetWorkspaceAgentsByWorkspaceAndBuildNumber", s.Mocked(func(dbm *dbmock.MockStore, faker *gofakeit.Faker, check *expects) {
 		w := testutil.Fake(s.T(), faker, database.Workspace{})
 		agt := testutil.Fake(s.T(), faker, database.WorkspaceAgent{})

coderd/database/dbmock/dbmock.go

@@ -1055,6 +1055,20 @@ func (mr *MockStoreMockRecorder) DeleteWorkspaceACLByID(ctx, id any) *gomock.Cal
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteWorkspaceACLByID", reflect.TypeOf((*MockStore)(nil).DeleteWorkspaceACLByID), ctx, id)
 }
 
+// DeleteWorkspaceACLsByOrganization mocks base method.
+func (m *MockStore) DeleteWorkspaceACLsByOrganization(ctx context.Context, organizationID uuid.UUID) error {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "DeleteWorkspaceACLsByOrganization", ctx, organizationID)
+	ret0, _ := ret[0].(error)
+	return ret0
+}
+
+// DeleteWorkspaceACLsByOrganization indicates an expected call of DeleteWorkspaceACLsByOrganization.
+func (mr *MockStoreMockRecorder) DeleteWorkspaceACLsByOrganization(ctx, organizationID any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "DeleteWorkspaceACLsByOrganization", reflect.TypeOf((*MockStore)(nil).DeleteWorkspaceACLsByOrganization), ctx, organizationID)
+}
+
 // DeleteWorkspaceAgentPortShare mocks base method.
 func (m *MockStore) DeleteWorkspaceAgentPortShare(ctx context.Context, arg database.DeleteWorkspaceAgentPortShareParams) error {
 	m.ctrl.T.Helper()
@@ -4123,6 +4137,21 @@ func (mr *MockStoreMockRecorder) GetWorkspaceAgentAndLatestBuildByAuthToken(ctx,
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetWorkspaceAgentAndLatestBuildByAuthToken", reflect.TypeOf((*MockStore)(nil).GetWorkspaceAgentAndLatestBuildByAuthToken), ctx, authToken)
 }
 
+// GetWorkspaceAgentAndWorkspaceByID mocks base method.
+func (m *MockStore) GetWorkspaceAgentAndWorkspaceByID(ctx context.Context, id uuid.UUID) (database.GetWorkspaceAgentAndWorkspaceByIDRow, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "GetWorkspaceAgentAndWorkspaceByID", ctx, id)
+	ret0, _ := ret[0].(database.GetWorkspaceAgentAndWorkspaceByIDRow)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// GetWorkspaceAgentAndWorkspaceByID indicates an expected call of GetWorkspaceAgentAndWorkspaceByID.
+func (mr *MockStoreMockRecorder) GetWorkspaceAgentAndWorkspaceByID(ctx, id any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "GetWorkspaceAgentAndWorkspaceByID", reflect.TypeOf((*MockStore)(nil).GetWorkspaceAgentAndWorkspaceByID), ctx, id)
+}
+
 // GetWorkspaceAgentByID mocks base method.
 func (m *MockStore) GetWorkspaceAgentByID(ctx context.Context, id uuid.UUID) (database.WorkspaceAgent, error) {
 	m.ctrl.T.Helper()
@@ -6645,6 +6674,21 @@ func (mr *MockStoreMockRecorder) UpdateOrganizationDeletedByID(ctx, arg any) *go
 	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateOrganizationDeletedByID", reflect.TypeOf((*MockStore)(nil).UpdateOrganizationDeletedByID), ctx, arg)
 }
 
+// UpdateOrganizationWorkspaceSharingSettings mocks base method.
+func (m *MockStore) UpdateOrganizationWorkspaceSharingSettings(ctx context.Context, arg database.UpdateOrganizationWorkspaceSharingSettingsParams) (database.Organization, error) {
+	m.ctrl.T.Helper()
+	ret := m.ctrl.Call(m, "UpdateOrganizationWorkspaceSharingSettings", ctx, arg)
+	ret0, _ := ret[0].(database.Organization)
+	ret1, _ := ret[1].(error)
+	return ret0, ret1
+}
+
+// UpdateOrganizationWorkspaceSharingSettings indicates an expected call of UpdateOrganizationWorkspaceSharingSettings.
+func (mr *MockStoreMockRecorder) UpdateOrganizationWorkspaceSharingSettings(ctx, arg any) *gomock.Call {
+	mr.mock.ctrl.T.Helper()
+	return mr.mock.ctrl.RecordCallWithMethodType(mr.mock, "UpdateOrganizationWorkspaceSharingSettings", reflect.TypeOf((*MockStore)(nil).UpdateOrganizationWorkspaceSharingSettings), ctx, arg)
+}
+
 // UpdatePrebuildProvisionerJobWithCancel mocks base method.
 func (m *MockStore) UpdatePrebuildProvisionerJobWithCancel(ctx context.Context, arg database.UpdatePrebuildProvisionerJobWithCancelParams) ([]database.UpdatePrebuildProvisionerJobWithCancelRow, error) {
 	m.ctrl.T.Helper()

coderd/database/dbpurge/dbpurge.go

@@ -34,6 +34,9 @@ const (
 	// long enough to cover the maximum interval of a heartbeat event (currently
 	// 1 hour) plus some buffer.
 	maxTelemetryHeartbeatAge = 24 * time.Hour
+	// Boundary telemetry data only needs to persist for 24 hours since snapshots
+	// are taken every 30 minutes.
+	maxBoundaryTelemetryAge = 24 * time.Hour
 )
 
 // New creates a new periodically purging database instance.
@@ -127,6 +130,14 @@ func New(ctx context.Context, logger slog.Logger, db database.Store, vals *coder
 				return xerrors.Errorf("failed to delete old telemetry locks: %w", err)
 			}
 
+			deleteOldBoundaryTelemetryBefore := start.Add(-maxBoundaryTelemetryAge)
+			if err := tx.DeleteBoundaryActiveUsersBefore(ctx, deleteOldBoundaryTelemetryBefore); err != nil {
+				return xerrors.Errorf("failed to delete old boundary active users: %w", err)
+			}
+			if err := tx.DeleteBoundaryActiveWorkspacesBefore(ctx, deleteOldBoundaryTelemetryBefore); err != nil {
+				return xerrors.Errorf("failed to delete old boundary active workspaces: %w", err)
+			}
+
 			deleteOldAuditLogConnectionEventsBefore := start.Add(-maxAuditLogConnectionEventAge)
 			if err := tx.DeleteOldAuditLogConnectionEvents(ctx, database.DeleteOldAuditLogConnectionEventsParams{
 				BeforeTime: deleteOldAuditLogConnectionEventsBefore,

coderd/database/dump.sql

@@ -1182,6 +1182,19 @@ CREATE TABLE audit_logs (
     resource_icon text NOT NULL
 );
 
+CREATE TABLE boundary_active_users (
+    id uuid DEFAULT gen_random_uuid() NOT NULL,
+    user_id uuid NOT NULL,
+    recorded_at timestamp with time zone DEFAULT now() NOT NULL
+);
+
+CREATE TABLE boundary_active_workspaces (
+    id uuid DEFAULT gen_random_uuid() NOT NULL,
+    workspace_id uuid NOT NULL,
+    template_id uuid NOT NULL,
+    recorded_at timestamp with time zone DEFAULT now() NOT NULL
+);
+
 CREATE TABLE connection_logs (
     id uuid NOT NULL,
     connect_time timestamp with time zone NOT NULL,
@@ -3019,6 +3032,12 @@ ALTER TABLE ONLY api_keys
 ALTER TABLE ONLY audit_logs
     ADD CONSTRAINT audit_logs_pkey PRIMARY KEY (id);
 
+ALTER TABLE ONLY boundary_active_users
+    ADD CONSTRAINT boundary_active_users_pkey PRIMARY KEY (id);
+
+ALTER TABLE ONLY boundary_active_workspaces
+    ADD CONSTRAINT boundary_active_workspaces_pkey PRIMARY KEY (id);
+
 ALTER TABLE ONLY connection_logs
     ADD CONSTRAINT connection_logs_pkey PRIMARY KEY (id);
 
@@ -3350,6 +3369,14 @@ 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_boundary_active_users_recorded_at ON boundary_active_users USING btree (recorded_at);
+
+CREATE INDEX idx_boundary_active_users_user_id ON boundary_active_users USING btree (user_id);
+
+CREATE INDEX idx_boundary_active_workspaces_recorded_at ON boundary_active_workspaces USING btree (recorded_at);
+
+CREATE INDEX idx_boundary_active_workspaces_workspace_id ON boundary_active_workspaces USING btree (workspace_id);
+
 CREATE INDEX idx_connection_logs_connect_time_desc ON connection_logs USING btree (connect_time DESC);
 
 CREATE UNIQUE INDEX idx_connection_logs_connection_id_workspace_id_agent_name ON connection_logs USING btree (connection_id, workspace_id, agent_name);

coderd/database/migrations/000409_boundary_telemetry.down.sql

@@ -0,0 +1,2 @@
+DROP TABLE IF EXISTS boundary_active_workspaces;
+DROP TABLE IF EXISTS boundary_active_users;

coderd/database/migrations/000409_boundary_telemetry.up.sql

@@ -0,0 +1,21 @@
+-- Tables to track boundary feature usage for telemetry reporting.
+-- Data is collected from boundary log streams and inserted periodically by each replica.
+
+CREATE TABLE boundary_active_users (
+    id UUID PRIMARY KEY DEFAULT gen_random_uuid(),
+    user_id UUID NOT NULL,
+    recorded_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+);
+
+CREATE INDEX idx_boundary_active_users_user_id ON boundary_active_users(user_id);
+CREATE INDEX idx_boundary_active_users_recorded_at ON boundary_active_users(recorded_at);
+
+CREATE TABLE boundary_active_workspaces (
+    id UUID PRIMARY KEY DEFAULT gen_random_uuid(),
+    workspace_id UUID NOT NULL,
+    template_id UUID NOT NULL,
+    recorded_at TIMESTAMPTZ NOT NULL DEFAULT NOW()
+);
+
+CREATE INDEX idx_boundary_active_workspaces_workspace_id ON boundary_active_workspaces(workspace_id);
+CREATE INDEX idx_boundary_active_workspaces_recorded_at ON boundary_active_workspaces(recorded_at);

coderd/database/migrations/testdata/fixtures/000048_userdelete.up.sql

@@ -1,34 +1,34 @@
 -- This is a deleted user that shares the same username and linked_id as the existing user below.
 -- Any future migrations need to handle this case.
-INSERT INTO public.users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
+INSERT INTO users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
 	VALUES ('a0061a8e-7db7-4585-838c-3116a003dd21', 'githubuser@coder.com', 'githubuser', '\x', '2022-11-02 13:05:21.445455+02', '2022-11-02 13:05:21.445455+02', 'active', '{}', true) ON CONFLICT DO NOTHING;
-INSERT INTO public.organization_members VALUES ('a0061a8e-7db7-4585-838c-3116a003dd21', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
-INSERT INTO public.user_links(user_id, login_type, linked_id, oauth_access_token)
+INSERT INTO organization_members VALUES ('a0061a8e-7db7-4585-838c-3116a003dd21', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
+INSERT INTO user_links(user_id, login_type, linked_id, oauth_access_token)
 	VALUES('a0061a8e-7db7-4585-838c-3116a003dd21', 'github', '100', '');
 
 
-INSERT INTO public.users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
+INSERT INTO users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
 	VALUES ('fc1511ef-4fcf-4a3b-98a1-8df64160e35a', 'githubuser@coder.com', 'githubuser', '\x', '2022-11-02 13:05:21.445455+02', '2022-11-02 13:05:21.445455+02', 'active', '{}', false) ON CONFLICT DO NOTHING;
-INSERT INTO public.organization_members VALUES ('fc1511ef-4fcf-4a3b-98a1-8df64160e35a', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
-INSERT INTO public.user_links(user_id, login_type, linked_id, oauth_access_token)
+INSERT INTO organization_members VALUES ('fc1511ef-4fcf-4a3b-98a1-8df64160e35a', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
+INSERT INTO user_links(user_id, login_type, linked_id, oauth_access_token)
 	VALUES('fc1511ef-4fcf-4a3b-98a1-8df64160e35a', 'github', '100', '');
 
 -- Additionally, there is no unique constraint on user_id. So also add another user_link for the same user.
 -- This has happened on a production database.
-INSERT INTO public.user_links(user_id, login_type, linked_id, oauth_access_token)
+INSERT INTO user_links(user_id, login_type, linked_id, oauth_access_token)
 VALUES('fc1511ef-4fcf-4a3b-98a1-8df64160e35a', 'oidc', 'foo', '');
 
 
 -- Lastly, make 2 other users who have the same user link.
-INSERT INTO public.users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
+INSERT INTO users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
 VALUES ('580ed397-727d-4aaf-950a-51f89f556c24', 'dup_link_a@coder.com', 'dupe_a', '\x', '2022-11-02 13:05:21.445455+02', '2022-11-02 13:05:21.445455+02', 'active', '{}', false) ON CONFLICT DO NOTHING;
-INSERT INTO public.organization_members VALUES ('580ed397-727d-4aaf-950a-51f89f556c24', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
-INSERT INTO public.user_links(user_id, login_type, linked_id, oauth_access_token)
+INSERT INTO organization_members VALUES ('580ed397-727d-4aaf-950a-51f89f556c24', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
+INSERT INTO user_links(user_id, login_type, linked_id, oauth_access_token)
 VALUES('580ed397-727d-4aaf-950a-51f89f556c24', 'github', '500', '');
 
 
-INSERT INTO public.users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
+INSERT INTO users(id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, deleted)
 VALUES ('c813366b-2fde-45ae-920c-101c3ad6a1e1', 'dup_link_b@coder.com', 'dupe_b', '\x', '2022-11-02 13:05:21.445455+02', '2022-11-02 13:05:21.445455+02', 'active', '{}', false) ON CONFLICT DO NOTHING;
-INSERT INTO public.organization_members VALUES ('c813366b-2fde-45ae-920c-101c3ad6a1e1', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
-INSERT INTO public.user_links(user_id, login_type, linked_id, oauth_access_token)
+INSERT INTO organization_members VALUES ('c813366b-2fde-45ae-920c-101c3ad6a1e1', 'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', '2022-11-02 13:05:21.447595+02', '2022-11-02 13:05:21.447595+02', '{}') ON CONFLICT DO NOTHING;
+INSERT INTO user_links(user_id, login_type, linked_id, oauth_access_token)
 VALUES('c813366b-2fde-45ae-920c-101c3ad6a1e1', 'github', '500', '');

coderd/database/migrations/testdata/fixtures/000150_workspace_app_usage_stats.up.sql

@@ -1,4 +1,4 @@
-INSERT INTO public.workspace_app_stats (
+INSERT INTO workspace_app_stats (
 	id,
 	user_id,
 	workspace_id,

coderd/database/migrations/testdata/fixtures/000276_workspace_modules.up.sql

@@ -1,5 +1,5 @@
 INSERT INTO
-    public.workspace_modules (
+    workspace_modules (
         id,
         job_id,
         transition,

coderd/database/migrations/testdata/fixtures/000291_workspace_parameter_presets.up.sql

@@ -1,15 +1,15 @@
-INSERT INTO public.organizations (id, name, description, created_at, updated_at, is_default, display_name, icon) VALUES ('20362772-802a-4a72-8e4f-3648b4bfd168', 'strange_hopper58', 'wizardly_stonebraker60', '2025-02-07 07:46:19.507551 +00:00', '2025-02-07 07:46:19.507552 +00:00', false, 'competent_rhodes59', '');
+INSERT INTO organizations (id, name, description, created_at, updated_at, is_default, display_name, icon) VALUES ('20362772-802a-4a72-8e4f-3648b4bfd168', 'strange_hopper58', 'wizardly_stonebraker60', '2025-02-07 07:46:19.507551 +00:00', '2025-02-07 07:46:19.507552 +00:00', false, 'competent_rhodes59', '');
 
-INSERT INTO public.users (id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, login_type, avatar_url, deleted, last_seen_at, quiet_hours_schedule, theme_preference, name, github_com_user_id, hashed_one_time_passcode, one_time_passcode_expires_at) VALUES ('6c353aac-20de-467b-bdfb-3c30a37adcd2', 'vigorous_murdock61', 'affectionate_hawking62', 'lqTu9C5363AwD7NVNH6noaGjp91XIuZJ', '2025-02-07 07:46:19.510861 +00:00', '2025-02-07 07:46:19.512949 +00:00', 'active', '{}', 'password', '', false, '0001-01-01 00:00:00.000000', '', '', 'vigilant_hugle63', null, null, null);
+INSERT INTO users (id, email, username, hashed_password, created_at, updated_at, status, rbac_roles, login_type, avatar_url, deleted, last_seen_at, quiet_hours_schedule, theme_preference, name, github_com_user_id, hashed_one_time_passcode, one_time_passcode_expires_at) VALUES ('6c353aac-20de-467b-bdfb-3c30a37adcd2', 'vigorous_murdock61', 'affectionate_hawking62', 'lqTu9C5363AwD7NVNH6noaGjp91XIuZJ', '2025-02-07 07:46:19.510861 +00:00', '2025-02-07 07:46:19.512949 +00:00', 'active', '{}', 'password', '', false, '0001-01-01 00:00:00.000000', '', '', 'vigilant_hugle63', null, null, null);
 
-INSERT INTO public.templates (id, created_at, updated_at, organization_id, deleted, name, provisioner, active_version_id, description, default_ttl, created_by, icon, user_acl, group_acl, display_name, allow_user_cancel_workspace_jobs, allow_user_autostart, allow_user_autostop, failure_ttl, time_til_dormant, time_til_dormant_autodelete, autostop_requirement_days_of_week, autostop_requirement_weeks, autostart_block_days_of_week, require_active_version, deprecated, activity_bump, max_port_sharing_level) VALUES ('6b298946-7a4f-47ac-9158-b03b08740a41', '2025-02-07 07:46:19.513317 +00:00', '2025-02-07 07:46:19.513317 +00:00', '20362772-802a-4a72-8e4f-3648b4bfd168', false, 'modest_leakey64', 'echo', 'e6cfa2a4-e4cf-4182-9e19-08b975682a28', 'upbeat_wright65', 604800000000000, '6c353aac-20de-467b-bdfb-3c30a37adcd2', 'nervous_keller66', '{}', '{"20362772-802a-4a72-8e4f-3648b4bfd168": ["read", "use"]}', 'determined_aryabhata67', false, true, true, 0, 0, 0, 0, 0, 0, false, '', 3600000000000, 'owner');
-INSERT INTO public.template_versions (id, template_id, organization_id, created_at, updated_at, name, readme, job_id, created_by, external_auth_providers, message, archived, source_example_id) VALUES ('af58bd62-428c-4c33-849b-d43a3be07d93', '6b298946-7a4f-47ac-9158-b03b08740a41', '20362772-802a-4a72-8e4f-3648b4bfd168', '2025-02-07 07:46:19.514782 +00:00', '2025-02-07 07:46:19.514782 +00:00', 'distracted_shockley68', 'sleepy_turing69', 'f2e2ea1c-5aa3-4a1d-8778-2e5071efae59', '6c353aac-20de-467b-bdfb-3c30a37adcd2', '[]', '', false, null);
+INSERT INTO templates (id, created_at, updated_at, organization_id, deleted, name, provisioner, active_version_id, description, default_ttl, created_by, icon, user_acl, group_acl, display_name, allow_user_cancel_workspace_jobs, allow_user_autostart, allow_user_autostop, failure_ttl, time_til_dormant, time_til_dormant_autodelete, autostop_requirement_days_of_week, autostop_requirement_weeks, autostart_block_days_of_week, require_active_version, deprecated, activity_bump, max_port_sharing_level) VALUES ('6b298946-7a4f-47ac-9158-b03b08740a41', '2025-02-07 07:46:19.513317 +00:00', '2025-02-07 07:46:19.513317 +00:00', '20362772-802a-4a72-8e4f-3648b4bfd168', false, 'modest_leakey64', 'echo', 'e6cfa2a4-e4cf-4182-9e19-08b975682a28', 'upbeat_wright65', 604800000000000, '6c353aac-20de-467b-bdfb-3c30a37adcd2', 'nervous_keller66', '{}', '{"20362772-802a-4a72-8e4f-3648b4bfd168": ["read", "use"]}', 'determined_aryabhata67', false, true, true, 0, 0, 0, 0, 0, 0, false, '', 3600000000000, 'owner');
+INSERT INTO template_versions (id, template_id, organization_id, created_at, updated_at, name, readme, job_id, created_by, external_auth_providers, message, archived, source_example_id) VALUES ('af58bd62-428c-4c33-849b-d43a3be07d93', '6b298946-7a4f-47ac-9158-b03b08740a41', '20362772-802a-4a72-8e4f-3648b4bfd168', '2025-02-07 07:46:19.514782 +00:00', '2025-02-07 07:46:19.514782 +00:00', 'distracted_shockley68', 'sleepy_turing69', 'f2e2ea1c-5aa3-4a1d-8778-2e5071efae59', '6c353aac-20de-467b-bdfb-3c30a37adcd2', '[]', '', false, null);
 
-INSERT INTO public.template_version_presets (id, template_version_id, name, created_at) VALUES ('28b42cc0-c4fe-4907-a0fe-e4d20f1e9bfe', 'af58bd62-428c-4c33-849b-d43a3be07d93', 'test', '0001-01-01 00:00:00.000000 +00:00');
+INSERT INTO template_version_presets (id, template_version_id, name, created_at) VALUES ('28b42cc0-c4fe-4907-a0fe-e4d20f1e9bfe', 'af58bd62-428c-4c33-849b-d43a3be07d93', 'test', '0001-01-01 00:00:00.000000 +00:00');
 
 -- Add presets with the same template version ID and name
 -- to ensure they're correctly handled by the 00031*_preset_prebuilds migration.
-INSERT INTO public.template_version_presets (
+INSERT INTO template_version_presets (
 	id, template_version_id, name, created_at
 )
 VALUES (
@@ -19,7 +19,7 @@ VALUES (
 	'0001-01-01 00:00:00.000000 +00:00'
 );
 
-INSERT INTO public.template_version_presets (
+INSERT INTO template_version_presets (
 	id, template_version_id, name, created_at
 )
 VALUES (
@@ -29,4 +29,4 @@ VALUES (
 	'0001-01-01 00:00:00.000000 +00:00'
 );
 
-INSERT INTO public.template_version_preset_parameters (id, template_version_preset_id, name, value) VALUES ('ea90ccd2-5024-459e-87e4-879afd24de0f', '28b42cc0-c4fe-4907-a0fe-e4d20f1e9bfe', 'test', 'test');
+INSERT INTO template_version_preset_parameters (id, template_version_preset_id, name, value) VALUES ('ea90ccd2-5024-459e-87e4-879afd24de0f', '28b42cc0-c4fe-4907-a0fe-e4d20f1e9bfe', 'test', 'test');

coderd/database/migrations/testdata/fixtures/000366_create_tasks_data_model.up.sql

@@ -1,4 +1,4 @@
-INSERT INTO public.tasks VALUES (
+INSERT INTO tasks VALUES (
     'f5a1c3e4-8b2d-4f6a-9d7e-2a8b5c9e1f3d', -- id
     'bb640d07-ca8a-4869-b6bc-ae61ebb2fda1', -- organization_id
     '30095c71-380b-457a-8995-97b8ee6e5307', -- owner_id
@@ -11,7 +11,7 @@ INSERT INTO public.tasks VALUES (
     NULL                                    -- deleted_at
 ) ON CONFLICT DO NOTHING;
 
-INSERT INTO public.task_workspace_apps VALUES (
+INSERT INTO task_workspace_apps VALUES (
     'f5a1c3e4-8b2d-4f6a-9d7e-2a8b5c9e1f3d', -- task_id
     'a8c0b8c5-c9a8-4f33-93a4-8142e6858244', -- workspace_build_id
     '8fa17bbd-c48c-44c7-91ae-d4acbc755fad', -- workspace_agent_id

coderd/database/migrations/testdata/fixtures/000379_create_tasks_with_status_view.up.sql

@@ -1,4 +1,4 @@
-INSERT INTO public.task_workspace_apps VALUES (
+INSERT INTO task_workspace_apps VALUES (
     'f5a1c3e4-8b2d-4f6a-9d7e-2a8b5c9e1f3d', -- task_id
     NULL,                                   -- workspace_agent_id
     NULL,                                   -- workspace_app_id

coderd/database/modelmethods.go

@@ -884,3 +884,8 @@ func WorkspaceIdentityFromWorkspace(w Workspace) WorkspaceIdentity {
 		AutostartSchedule: w.AutostartSchedule,
 	}
 }
+
+// A workspace agent belongs to the owner of the associated workspace.
+func (r GetWorkspaceAgentAndWorkspaceByIDRow) RBACObject() rbac.Object {
+	return r.WorkspaceTable.RBACObject()
+}

coderd/database/models.go

@@ -3693,6 +3693,19 @@ type AuditLog struct {
 	ResourceIcon     string          `db:"resource_icon" json:"resource_icon"`
 }
 
+type BoundaryActiveUser struct {
+	ID         uuid.UUID `db:"id" json:"id"`
+	UserID     uuid.UUID `db:"user_id" json:"user_id"`
+	RecordedAt time.Time `db:"recorded_at" json:"recorded_at"`
+}
+
+type BoundaryActiveWorkspace struct {
+	ID          uuid.UUID `db:"id" json:"id"`
+	WorkspaceID uuid.UUID `db:"workspace_id" json:"workspace_id"`
+	TemplateID  uuid.UUID `db:"template_id" json:"template_id"`
+	RecordedAt  time.Time `db:"recorded_at" json:"recorded_at"`
+}
+
 type ConnectionLog struct {
 	ID               uuid.UUID      `db:"id" json:"id"`
 	ConnectTime      time.Time      `db:"connect_time" json:"connect_time"`

coderd/database/querier.go

@@ -88,6 +88,8 @@ type sqlcQuerier interface {
 	// be recreated.
 	DeleteAllWebpushSubscriptions(ctx context.Context) error
 	DeleteApplicationConnectAPIKeysByUserID(ctx context.Context, userID uuid.UUID) error
+	DeleteBoundaryActiveUsersBefore(ctx context.Context, recordedAt time.Time) error
+	DeleteBoundaryActiveWorkspacesBefore(ctx context.Context, recordedAt time.Time) error
 	DeleteCoordinator(ctx context.Context, id uuid.UUID) error
 	DeleteCryptoKey(ctx context.Context, arg DeleteCryptoKeyParams) (CryptoKey, error)
 	DeleteCustomRole(ctx context.Context, arg DeleteCustomRoleParams) error
@@ -139,6 +141,7 @@ type sqlcQuerier interface {
 	DeleteWebpushSubscriptionByUserIDAndEndpoint(ctx context.Context, arg DeleteWebpushSubscriptionByUserIDAndEndpointParams) error
 	DeleteWebpushSubscriptions(ctx context.Context, ids []uuid.UUID) error
 	DeleteWorkspaceACLByID(ctx context.Context, id uuid.UUID) error
+	DeleteWorkspaceACLsByOrganization(ctx context.Context, organizationID uuid.UUID) error
 	DeleteWorkspaceAgentPortShare(ctx context.Context, arg DeleteWorkspaceAgentPortShareParams) error
 	DeleteWorkspaceAgentPortSharesByTemplate(ctx context.Context, templateID uuid.UUID) error
 	DeleteWorkspaceSubAgentByID(ctx context.Context, id uuid.UUID) error
@@ -192,6 +195,8 @@ type sqlcQuerier interface {
 	// This function returns roles for authorization purposes. Implied member roles
 	// are included.
 	GetAuthorizationUserRoles(ctx context.Context, userID uuid.UUID) (GetAuthorizationUserRolesRow, error)
+	GetBoundaryActiveUsersSince(ctx context.Context, recordedAt time.Time) ([]uuid.UUID, error)
+	GetBoundaryActiveWorkspacesSince(ctx context.Context, recordedAt time.Time) ([]GetBoundaryActiveWorkspacesSinceRow, error)
 	GetConnectionLogsOffset(ctx context.Context, arg GetConnectionLogsOffsetParams) ([]GetConnectionLogsOffsetRow, error)
 	GetCoordinatorResumeTokenSigningKey(ctx context.Context) (string, error)
 	GetCryptoKeyByFeatureAndSequence(ctx context.Context, arg GetCryptoKeyByFeatureAndSequenceParams) (CryptoKey, error)
@@ -466,6 +471,7 @@ type sqlcQuerier interface {
 	GetWebpushVAPIDKeys(ctx context.Context) (GetWebpushVAPIDKeysRow, error)
 	GetWorkspaceACLByID(ctx context.Context, id uuid.UUID) (GetWorkspaceACLByIDRow, error)
 	GetWorkspaceAgentAndLatestBuildByAuthToken(ctx context.Context, authToken uuid.UUID) (GetWorkspaceAgentAndLatestBuildByAuthTokenRow, error)
+	GetWorkspaceAgentAndWorkspaceByID(ctx context.Context, id uuid.UUID) (GetWorkspaceAgentAndWorkspaceByIDRow, error)
 	GetWorkspaceAgentByID(ctx context.Context, id uuid.UUID) (WorkspaceAgent, error)
 	GetWorkspaceAgentByInstanceID(ctx context.Context, authInstanceID string) (WorkspaceAgent, error)
 	GetWorkspaceAgentDevcontainersByAgentID(ctx context.Context, workspaceAgentID uuid.UUID) ([]WorkspaceAgentDevcontainer, error)
@@ -543,6 +549,8 @@ type sqlcQuerier interface {
 	// every member of the org.
 	InsertAllUsersGroup(ctx context.Context, organizationID uuid.UUID) (Group, error)
 	InsertAuditLog(ctx context.Context, arg InsertAuditLogParams) (AuditLog, error)
+	InsertBoundaryActiveUser(ctx context.Context, arg InsertBoundaryActiveUserParams) error
+	InsertBoundaryActiveWorkspace(ctx context.Context, arg InsertBoundaryActiveWorkspaceParams) error
 	InsertCryptoKey(ctx context.Context, arg InsertCryptoKeyParams) (CryptoKey, error)
 	InsertCustomRole(ctx context.Context, arg InsertCustomRoleParams) (CustomRole, error)
 	InsertDBCryptKey(ctx context.Context, arg InsertDBCryptKeyParams) error
@@ -677,6 +685,7 @@ type sqlcQuerier interface {
 	UpdateOAuth2ProviderAppSecretByID(ctx context.Context, arg UpdateOAuth2ProviderAppSecretByIDParams) (OAuth2ProviderAppSecret, error)
 	UpdateOrganization(ctx context.Context, arg UpdateOrganizationParams) (Organization, error)
 	UpdateOrganizationDeletedByID(ctx context.Context, arg UpdateOrganizationDeletedByIDParams) error
+	UpdateOrganizationWorkspaceSharingSettings(ctx context.Context, arg UpdateOrganizationWorkspaceSharingSettingsParams) (Organization, error)
 	// Cancels all pending provisioner jobs for prebuilt workspaces on a specific preset from an
 	// inactive template version.
 	// This is an optimization to clean up stale pending jobs.

coderd/database/querier_test.go

@@ -2304,6 +2304,94 @@ func TestDeleteCustomRoleDoesNotDeleteSystemRole(t *testing.T) {
 	require.True(t, roles[0].IsSystem)
 }
 
+func TestUpdateOrganizationWorkspaceSharingSettings(t *testing.T) {
+	t.Parallel()
+
+	db, _ := dbtestutil.NewDB(t)
+	org := dbgen.Organization(t, db, database.Organization{})
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+
+	updated, err := db.UpdateOrganizationWorkspaceSharingSettings(ctx, database.UpdateOrganizationWorkspaceSharingSettingsParams{
+		ID:                       org.ID,
+		WorkspaceSharingDisabled: true,
+		UpdatedAt:                dbtime.Now(),
+	})
+	require.NoError(t, err)
+	require.True(t, updated.WorkspaceSharingDisabled)
+
+	got, err := db.GetOrganizationByID(ctx, org.ID)
+	require.NoError(t, err)
+	require.True(t, got.WorkspaceSharingDisabled)
+}
+
+func TestDeleteWorkspaceACLsByOrganization(t *testing.T) {
+	t.Parallel()
+
+	db, _ := dbtestutil.NewDB(t)
+	org1 := dbgen.Organization(t, db, database.Organization{})
+	org2 := dbgen.Organization(t, db, database.Organization{})
+
+	owner1 := dbgen.User(t, db, database.User{})
+	owner2 := dbgen.User(t, db, database.User{})
+	sharedUser := dbgen.User(t, db, database.User{})
+	sharedGroup := dbgen.Group(t, db, database.Group{
+		OrganizationID: org1.ID,
+	})
+
+	dbgen.OrganizationMember(t, db, database.OrganizationMember{
+		OrganizationID: org1.ID,
+		UserID:         owner1.ID,
+	})
+	dbgen.OrganizationMember(t, db, database.OrganizationMember{
+		OrganizationID: org2.ID,
+		UserID:         owner2.ID,
+	})
+	dbgen.OrganizationMember(t, db, database.OrganizationMember{
+		OrganizationID: org1.ID,
+		UserID:         sharedUser.ID,
+	})
+
+	ws1 := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
+		OwnerID:        owner1.ID,
+		OrganizationID: org1.ID,
+		UserACL: database.WorkspaceACL{
+			sharedUser.ID.String(): {
+				Permissions: []policy.Action{policy.ActionRead},
+			},
+		},
+		GroupACL: database.WorkspaceACL{
+			sharedGroup.ID.String(): {
+				Permissions: []policy.Action{policy.ActionRead},
+			},
+		},
+	}).Do().Workspace
+
+	ws2 := dbfake.WorkspaceBuild(t, db, database.WorkspaceTable{
+		OwnerID:        owner2.ID,
+		OrganizationID: org2.ID,
+		UserACL: database.WorkspaceACL{
+			uuid.NewString(): {
+				Permissions: []policy.Action{policy.ActionRead},
+			},
+		},
+	}).Do().Workspace
+
+	ctx := testutil.Context(t, testutil.WaitShort)
+
+	err := db.DeleteWorkspaceACLsByOrganization(ctx, org1.ID)
+	require.NoError(t, err)
+
+	got1, err := db.GetWorkspaceByID(ctx, ws1.ID)
+	require.NoError(t, err)
+	require.Empty(t, got1.UserACL)
+	require.Empty(t, got1.GroupACL)
+
+	got2, err := db.GetWorkspaceByID(ctx, ws2.ID)
+	require.NoError(t, err)
+	require.NotEmpty(t, got2.UserACL)
+}
+
 func TestAuthorizedAuditLogs(t *testing.T) {
 	t.Parallel()
 

coderd/database/queries.sql.go

@@ -1980,6 +1980,116 @@ func (q *sqlQuerier) InsertAuditLog(ctx context.Context, arg InsertAuditLogParam
 	return i, err
 }
 
+const deleteBoundaryActiveUsersBefore = `-- name: DeleteBoundaryActiveUsersBefore :exec
+DELETE FROM boundary_active_users WHERE recorded_at < $1
+`
+
+func (q *sqlQuerier) DeleteBoundaryActiveUsersBefore(ctx context.Context, recordedAt time.Time) error {
+	_, err := q.db.ExecContext(ctx, deleteBoundaryActiveUsersBefore, recordedAt)
+	return err
+}
+
+const deleteBoundaryActiveWorkspacesBefore = `-- name: DeleteBoundaryActiveWorkspacesBefore :exec
+DELETE FROM boundary_active_workspaces WHERE recorded_at < $1
+`
+
+func (q *sqlQuerier) DeleteBoundaryActiveWorkspacesBefore(ctx context.Context, recordedAt time.Time) error {
+	_, err := q.db.ExecContext(ctx, deleteBoundaryActiveWorkspacesBefore, recordedAt)
+	return err
+}
+
+const getBoundaryActiveUsersSince = `-- name: GetBoundaryActiveUsersSince :many
+SELECT DISTINCT user_id FROM boundary_active_users
+WHERE recorded_at > $1
+`
+
+func (q *sqlQuerier) GetBoundaryActiveUsersSince(ctx context.Context, recordedAt time.Time) ([]uuid.UUID, error) {
+	rows, err := q.db.QueryContext(ctx, getBoundaryActiveUsersSince, recordedAt)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []uuid.UUID
+	for rows.Next() {
+		var user_id uuid.UUID
+		if err := rows.Scan(&user_id); err != nil {
+			return nil, err
+		}
+		items = append(items, user_id)
+	}
+	if err := rows.Close(); err != nil {
+		return nil, err
+	}
+	if err := rows.Err(); err != nil {
+		return nil, err
+	}
+	return items, nil
+}
+
+const getBoundaryActiveWorkspacesSince = `-- name: GetBoundaryActiveWorkspacesSince :many
+SELECT DISTINCT workspace_id, template_id FROM boundary_active_workspaces
+WHERE recorded_at > $1
+`
+
+type GetBoundaryActiveWorkspacesSinceRow struct {
+	WorkspaceID uuid.UUID `db:"workspace_id" json:"workspace_id"`
+	TemplateID  uuid.UUID `db:"template_id" json:"template_id"`
+}
+
+func (q *sqlQuerier) GetBoundaryActiveWorkspacesSince(ctx context.Context, recordedAt time.Time) ([]GetBoundaryActiveWorkspacesSinceRow, error) {
+	rows, err := q.db.QueryContext(ctx, getBoundaryActiveWorkspacesSince, recordedAt)
+	if err != nil {
+		return nil, err
+	}
+	defer rows.Close()
+	var items []GetBoundaryActiveWorkspacesSinceRow
+	for rows.Next() {
+		var i GetBoundaryActiveWorkspacesSinceRow
+		if err := rows.Scan(&i.WorkspaceID, &i.TemplateID); 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
+}
+
+const insertBoundaryActiveUser = `-- name: InsertBoundaryActiveUser :exec
+INSERT INTO boundary_active_users (user_id, recorded_at)
+VALUES ($1, $2)
+`
+
+type InsertBoundaryActiveUserParams struct {
+	UserID     uuid.UUID `db:"user_id" json:"user_id"`
+	RecordedAt time.Time `db:"recorded_at" json:"recorded_at"`
+}
+
+func (q *sqlQuerier) InsertBoundaryActiveUser(ctx context.Context, arg InsertBoundaryActiveUserParams) error {
+	_, err := q.db.ExecContext(ctx, insertBoundaryActiveUser, arg.UserID, arg.RecordedAt)
+	return err
+}
+
+const insertBoundaryActiveWorkspace = `-- name: InsertBoundaryActiveWorkspace :exec
+INSERT INTO boundary_active_workspaces (workspace_id, template_id, recorded_at)
+VALUES ($1, $2, $3)
+`
+
+type InsertBoundaryActiveWorkspaceParams struct {
+	WorkspaceID uuid.UUID `db:"workspace_id" json:"workspace_id"`
+	TemplateID  uuid.UUID `db:"template_id" json:"template_id"`
+	RecordedAt  time.Time `db:"recorded_at" json:"recorded_at"`
+}
+
+func (q *sqlQuerier) InsertBoundaryActiveWorkspace(ctx context.Context, arg InsertBoundaryActiveWorkspaceParams) error {
+	_, err := q.db.ExecContext(ctx, insertBoundaryActiveWorkspace, arg.WorkspaceID, arg.TemplateID, arg.RecordedAt)
+	return err
+}
+
 const countConnectionLogs = `-- name: CountConnectionLogs :one
 SELECT
 	COUNT(*) AS count
@@ -8197,6 +8307,41 @@ func (q *sqlQuerier) UpdateOrganizationDeletedByID(ctx context.Context, arg Upda
 	return err
 }
 
+const updateOrganizationWorkspaceSharingSettings = `-- name: UpdateOrganizationWorkspaceSharingSettings :one
+UPDATE
+    organizations
+SET
+    workspace_sharing_disabled = $1,
+    updated_at = $2
+WHERE
+    id = $3
+RETURNING id, name, description, created_at, updated_at, is_default, display_name, icon, deleted, workspace_sharing_disabled
+`
+
+type UpdateOrganizationWorkspaceSharingSettingsParams struct {
+	WorkspaceSharingDisabled bool      `db:"workspace_sharing_disabled" json:"workspace_sharing_disabled"`
+	UpdatedAt                time.Time `db:"updated_at" json:"updated_at"`
+	ID                       uuid.UUID `db:"id" json:"id"`
+}
+
+func (q *sqlQuerier) UpdateOrganizationWorkspaceSharingSettings(ctx context.Context, arg UpdateOrganizationWorkspaceSharingSettingsParams) (Organization, error) {
+	row := q.db.QueryRowContext(ctx, updateOrganizationWorkspaceSharingSettings, arg.WorkspaceSharingDisabled, arg.UpdatedAt, arg.ID)
+	var i Organization
+	err := row.Scan(
+		&i.ID,
+		&i.Name,
+		&i.Description,
+		&i.CreatedAt,
+		&i.UpdatedAt,
+		&i.IsDefault,
+		&i.DisplayName,
+		&i.Icon,
+		&i.Deleted,
+		&i.WorkspaceSharingDisabled,
+	)
+	return i, err
+}
+
 const getParameterSchemasByJobID = `-- name: GetParameterSchemasByJobID :many
 SELECT
 	id, created_at, job_id, name, description, default_source_scheme, default_source_value, allow_override_source, default_destination_scheme, allow_override_destination, default_refresh, redisplay_value, validation_error, validation_condition, validation_type_system, validation_value_type, index
@@ -18120,6 +18265,99 @@ func (q *sqlQuerier) GetWorkspaceAgentAndLatestBuildByAuthToken(ctx context.Cont
 	return i, err
 }
 
+const getWorkspaceAgentAndWorkspaceByID = `-- name: GetWorkspaceAgentAndWorkspaceByID :one
+SELECT
+	workspace_agents.id, workspace_agents.created_at, workspace_agents.updated_at, workspace_agents.name, workspace_agents.first_connected_at, workspace_agents.last_connected_at, workspace_agents.disconnected_at, workspace_agents.resource_id, workspace_agents.auth_token, workspace_agents.auth_instance_id, workspace_agents.architecture, workspace_agents.environment_variables, workspace_agents.operating_system, workspace_agents.instance_metadata, workspace_agents.resource_metadata, workspace_agents.directory, workspace_agents.version, workspace_agents.last_connected_replica_id, workspace_agents.connection_timeout_seconds, workspace_agents.troubleshooting_url, workspace_agents.motd_file, workspace_agents.lifecycle_state, workspace_agents.expanded_directory, workspace_agents.logs_length, workspace_agents.logs_overflowed, workspace_agents.started_at, workspace_agents.ready_at, workspace_agents.subsystems, workspace_agents.display_apps, workspace_agents.api_version, workspace_agents.display_order, workspace_agents.parent_id, workspace_agents.api_key_scope, workspace_agents.deleted,
+	workspaces.id, workspaces.created_at, workspaces.updated_at, workspaces.owner_id, workspaces.organization_id, workspaces.template_id, workspaces.deleted, workspaces.name, workspaces.autostart_schedule, workspaces.ttl, workspaces.last_used_at, workspaces.dormant_at, workspaces.deleting_at, workspaces.automatic_updates, workspaces.favorite, workspaces.next_start_at, workspaces.group_acl, workspaces.user_acl,
+	users.username as owner_username
+FROM
+	workspace_agents
+JOIN
+	workspace_resources ON workspace_agents.resource_id = workspace_resources.id
+JOIN
+	provisioner_jobs ON workspace_resources.job_id = provisioner_jobs.id
+JOIN
+	workspace_builds ON provisioner_jobs.id = workspace_builds.job_id
+JOIN
+	workspaces ON workspace_builds.workspace_id = workspaces.id
+JOIN
+	users ON workspaces.owner_id = users.id
+WHERE
+	workspace_agents.id = $1
+	AND workspace_agents.deleted = FALSE
+	AND provisioner_jobs.type = 'workspace_build'::provisioner_job_type
+	AND workspaces.deleted = FALSE
+	AND users.deleted = FALSE
+LIMIT 1
+`
+
+type GetWorkspaceAgentAndWorkspaceByIDRow struct {
+	WorkspaceAgent WorkspaceAgent `db:"workspace_agent" json:"workspace_agent"`
+	WorkspaceTable WorkspaceTable `db:"workspace_table" json:"workspace_table"`
+	OwnerUsername  string         `db:"owner_username" json:"owner_username"`
+}
+
+func (q *sqlQuerier) GetWorkspaceAgentAndWorkspaceByID(ctx context.Context, id uuid.UUID) (GetWorkspaceAgentAndWorkspaceByIDRow, error) {
+	row := q.db.QueryRowContext(ctx, getWorkspaceAgentAndWorkspaceByID, id)
+	var i GetWorkspaceAgentAndWorkspaceByIDRow
+	err := row.Scan(
+		&i.WorkspaceAgent.ID,
+		&i.WorkspaceAgent.CreatedAt,
+		&i.WorkspaceAgent.UpdatedAt,
+		&i.WorkspaceAgent.Name,
+		&i.WorkspaceAgent.FirstConnectedAt,
+		&i.WorkspaceAgent.LastConnectedAt,
+		&i.WorkspaceAgent.DisconnectedAt,
+		&i.WorkspaceAgent.ResourceID,
+		&i.WorkspaceAgent.AuthToken,
+		&i.WorkspaceAgent.AuthInstanceID,
+		&i.WorkspaceAgent.Architecture,
+		&i.WorkspaceAgent.EnvironmentVariables,
+		&i.WorkspaceAgent.OperatingSystem,
+		&i.WorkspaceAgent.InstanceMetadata,
+		&i.WorkspaceAgent.ResourceMetadata,
+		&i.WorkspaceAgent.Directory,
+		&i.WorkspaceAgent.Version,
+		&i.WorkspaceAgent.LastConnectedReplicaID,
+		&i.WorkspaceAgent.ConnectionTimeoutSeconds,
+		&i.WorkspaceAgent.TroubleshootingURL,
+		&i.WorkspaceAgent.MOTDFile,
+		&i.WorkspaceAgent.LifecycleState,
+		&i.WorkspaceAgent.ExpandedDirectory,
+		&i.WorkspaceAgent.LogsLength,
+		&i.WorkspaceAgent.LogsOverflowed,
+		&i.WorkspaceAgent.StartedAt,
+		&i.WorkspaceAgent.ReadyAt,
+		pq.Array(&i.WorkspaceAgent.Subsystems),
+		pq.Array(&i.WorkspaceAgent.DisplayApps),
+		&i.WorkspaceAgent.APIVersion,
+		&i.WorkspaceAgent.DisplayOrder,
+		&i.WorkspaceAgent.ParentID,
+		&i.WorkspaceAgent.APIKeyScope,
+		&i.WorkspaceAgent.Deleted,
+		&i.WorkspaceTable.ID,
+		&i.WorkspaceTable.CreatedAt,
+		&i.WorkspaceTable.UpdatedAt,
+		&i.WorkspaceTable.OwnerID,
+		&i.WorkspaceTable.OrganizationID,
+		&i.WorkspaceTable.TemplateID,
+		&i.WorkspaceTable.Deleted,
+		&i.WorkspaceTable.Name,
+		&i.WorkspaceTable.AutostartSchedule,
+		&i.WorkspaceTable.Ttl,
+		&i.WorkspaceTable.LastUsedAt,
+		&i.WorkspaceTable.DormantAt,
+		&i.WorkspaceTable.DeletingAt,
+		&i.WorkspaceTable.AutomaticUpdates,
+		&i.WorkspaceTable.Favorite,
+		&i.WorkspaceTable.NextStartAt,
+		&i.WorkspaceTable.GroupACL,
+		&i.WorkspaceTable.UserACL,
+		&i.OwnerUsername,
+	)
+	return i, err
+}
+
 const getWorkspaceAgentByID = `-- name: GetWorkspaceAgentByID :one
 SELECT
 	id, created_at, updated_at, name, first_connected_at, last_connected_at, disconnected_at, resource_id, auth_token, auth_instance_id, architecture, environment_variables, operating_system, instance_metadata, resource_metadata, directory, version, last_connected_replica_id, connection_timeout_seconds, troubleshooting_url, motd_file, lifecycle_state, expanded_directory, logs_length, logs_overflowed, started_at, ready_at, subsystems, display_apps, api_version, display_order, parent_id, api_key_scope, deleted
@@ -22151,6 +22389,21 @@ func (q *sqlQuerier) DeleteWorkspaceACLByID(ctx context.Context, id uuid.UUID) e
 	return err
 }
 
+const deleteWorkspaceACLsByOrganization = `-- name: DeleteWorkspaceACLsByOrganization :exec
+UPDATE
+	workspaces
+SET
+	group_acl = '{}'::jsonb,
+	user_acl = '{}'::jsonb
+WHERE
+	organization_id = $1
+`
+
+func (q *sqlQuerier) DeleteWorkspaceACLsByOrganization(ctx context.Context, organizationID uuid.UUID) error {
+	_, err := q.db.ExecContext(ctx, deleteWorkspaceACLsByOrganization, organizationID)
+	return err
+}
+
 const favoriteWorkspace = `-- name: FavoriteWorkspace :exec
 UPDATE workspaces SET favorite = true WHERE id = $1
 `

coderd/database/queries/boundarytelemetry.sql

@@ -0,0 +1,21 @@
+-- name: InsertBoundaryActiveUser :exec
+INSERT INTO boundary_active_users (user_id, recorded_at)
+VALUES ($1, $2);
+
+-- name: InsertBoundaryActiveWorkspace :exec
+INSERT INTO boundary_active_workspaces (workspace_id, template_id, recorded_at)
+VALUES ($1, $2, $3);
+
+-- name: GetBoundaryActiveUsersSince :many
+SELECT DISTINCT user_id FROM boundary_active_users
+WHERE recorded_at > $1;
+
+-- name: GetBoundaryActiveWorkspacesSince :many
+SELECT DISTINCT workspace_id, template_id FROM boundary_active_workspaces
+WHERE recorded_at > $1;
+
+-- name: DeleteBoundaryActiveUsersBefore :exec
+DELETE FROM boundary_active_users WHERE recorded_at < $1;
+
+-- name: DeleteBoundaryActiveWorkspacesBefore :exec
+DELETE FROM boundary_active_workspaces WHERE recorded_at < $1;

coderd/database/queries/organizations.sql

@@ -143,3 +143,13 @@ WHERE
     id = @id AND
     is_default = false;
 
+-- name: UpdateOrganizationWorkspaceSharingSettings :one
+UPDATE
+    organizations
+SET
+    workspace_sharing_disabled = @workspace_sharing_disabled,
+    updated_at = @updated_at
+WHERE
+    id = @id
+RETURNING *;
+

coderd/database/queries/workspaceagents.sql

@@ -393,3 +393,28 @@ AND wb.build_number = (
     WHERE wb2.workspace_id = w.id
 )
 AND workspace_agents.deleted = FALSE;
+
+-- name: GetWorkspaceAgentAndWorkspaceByID :one
+SELECT
+	sqlc.embed(workspace_agents),
+	sqlc.embed(workspaces),
+	users.username as owner_username
+FROM
+	workspace_agents
+JOIN
+	workspace_resources ON workspace_agents.resource_id = workspace_resources.id
+JOIN
+	provisioner_jobs ON workspace_resources.job_id = provisioner_jobs.id
+JOIN
+	workspace_builds ON provisioner_jobs.id = workspace_builds.job_id
+JOIN
+	workspaces ON workspace_builds.workspace_id = workspaces.id
+JOIN
+	users ON workspaces.owner_id = users.id
+WHERE
+	workspace_agents.id = @id
+	AND workspace_agents.deleted = FALSE
+	AND provisioner_jobs.type = 'workspace_build'::provisioner_job_type
+	AND workspaces.deleted = FALSE
+	AND users.deleted = FALSE
+LIMIT 1;

coderd/database/queries/workspaces.sql

@@ -947,6 +947,15 @@ SET
 WHERE
 	id = @id;
 
+-- name: DeleteWorkspaceACLsByOrganization :exec
+UPDATE
+	workspaces
+SET
+	group_acl = '{}'::jsonb,
+	user_acl = '{}'::jsonb
+WHERE
+	organization_id = @organization_id;
+
 -- name: GetRegularWorkspaceCreateMetrics :many
 -- Count regular workspaces: only those whose first successful 'start' build
 -- was not initiated by the prebuild system user.

coderd/database/unique_constraint.go

@@ -13,6 +13,8 @@ const (
 	UniqueAibridgeUserPromptsPkey                             UniqueConstraint = "aibridge_user_prompts_pkey"                                      // ALTER TABLE ONLY aibridge_user_prompts ADD CONSTRAINT aibridge_user_prompts_pkey PRIMARY KEY (id);
 	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);
+	UniqueBoundaryActiveUsersPkey                             UniqueConstraint = "boundary_active_users_pkey"                                      // ALTER TABLE ONLY boundary_active_users ADD CONSTRAINT boundary_active_users_pkey PRIMARY KEY (id);
+	UniqueBoundaryActiveWorkspacesPkey                        UniqueConstraint = "boundary_active_workspaces_pkey"                                 // ALTER TABLE ONLY boundary_active_workspaces ADD CONSTRAINT boundary_active_workspaces_pkey PRIMARY KEY (id);
 	UniqueConnectionLogsPkey                                  UniqueConstraint = "connection_logs_pkey"                                            // ALTER TABLE ONLY connection_logs ADD CONSTRAINT connection_logs_pkey PRIMARY KEY (id);
 	UniqueCryptoKeysPkey                                      UniqueConstraint = "crypto_keys_pkey"                                                // ALTER TABLE ONLY crypto_keys ADD CONSTRAINT crypto_keys_pkey PRIMARY KEY (feature, sequence);
 	UniqueCustomRolesUniqueKey                                UniqueConstraint = "custom_roles_unique_key"                                         // ALTER TABLE ONLY custom_roles ADD CONSTRAINT custom_roles_unique_key UNIQUE (name, organization_id);

coderd/debug.go

@@ -83,17 +83,21 @@ func (api *API) debugDeploymentHealth(rw http.ResponseWriter, r *http.Request) {
 		ctx, cancel := context.WithTimeout(context.Background(), api.Options.HealthcheckTimeout)
 		defer cancel()
 
-		report := api.HealthcheckFunc(ctx, apiKey)
+		// Create and store progress tracker for timeout diagnostics.
+		report := api.HealthcheckFunc(ctx, apiKey, &api.healthCheckProgress)
 		if report != nil { // Only store non-nil reports.
 			api.healthCheckCache.Store(report)
 		}
+		api.healthCheckProgress.Reset()
 		return report, nil
 	})
 
 	select {
 	case <-ctx.Done():
+		summary := api.healthCheckProgress.Summary()
 		httpapi.Write(ctx, rw, http.StatusServiceUnavailable, codersdk.Response{
-			Message: "Healthcheck is in progress and did not complete in time. Try again in a few seconds.",
+			Message: "Healthcheck timed out.",
+			Detail:  summary,
 		})
 		return
 	case res := <-resChan:

coderd/debug_test.go

@@ -14,6 +14,8 @@ import (
 
 	"cdr.dev/slog/v3/sloggers/slogtest"
 	"github.com/coder/coder/v2/coderd/coderdtest"
+	"github.com/coder/coder/v2/coderd/healthcheck"
+	"github.com/coder/coder/v2/codersdk"
 	"github.com/coder/coder/v2/codersdk/healthsdk"
 	"github.com/coder/coder/v2/testutil"
 )
@@ -28,7 +30,7 @@ func TestDebugHealth(t *testing.T) {
 			ctx, cancel  = context.WithTimeout(context.Background(), testutil.WaitShort)
 			sessionToken string
 			client       = coderdtest.New(t, &coderdtest.Options{
-				HealthcheckFunc: func(_ context.Context, apiKey string) *healthsdk.HealthcheckReport {
+				HealthcheckFunc: func(_ context.Context, apiKey string, _ *healthcheck.Progress) *healthsdk.HealthcheckReport {
 					calls.Add(1)
 					assert.Equal(t, sessionToken, apiKey)
 					return &healthsdk.HealthcheckReport{
@@ -61,7 +63,7 @@ func TestDebugHealth(t *testing.T) {
 			ctx, cancel  = context.WithTimeout(context.Background(), testutil.WaitShort)
 			sessionToken string
 			client       = coderdtest.New(t, &coderdtest.Options{
-				HealthcheckFunc: func(_ context.Context, apiKey string) *healthsdk.HealthcheckReport {
+				HealthcheckFunc: func(_ context.Context, apiKey string, _ *healthcheck.Progress) *healthsdk.HealthcheckReport {
 					calls.Add(1)
 					assert.Equal(t, sessionToken, apiKey)
 					return &healthsdk.HealthcheckReport{
@@ -93,19 +95,14 @@ func TestDebugHealth(t *testing.T) {
 			// Need to ignore errors due to ctx timeout
 			logger      = slogtest.Make(t, &slogtest.Options{IgnoreErrors: true})
 			ctx, cancel = context.WithTimeout(context.Background(), testutil.WaitShort)
+			done        = make(chan struct{})
 			client      = coderdtest.New(t, &coderdtest.Options{
 				Logger:             &logger,
-				HealthcheckTimeout: time.Microsecond,
-				HealthcheckFunc: func(context.Context, string) *healthsdk.HealthcheckReport {
-					t := time.NewTimer(time.Second)
-					defer t.Stop()
-
-					select {
-					case <-ctx.Done():
-						return &healthsdk.HealthcheckReport{}
-					case <-t.C:
-						return &healthsdk.HealthcheckReport{}
-					}
+				HealthcheckTimeout: time.Second,
+				HealthcheckFunc: func(_ context.Context, _ string, progress *healthcheck.Progress) *healthsdk.HealthcheckReport {
+					progress.Start("test")
+					<-done
+					return &healthsdk.HealthcheckReport{}
 				},
 			})
 			_ = coderdtest.CreateFirstUser(t, client)
@@ -115,8 +112,14 @@ func TestDebugHealth(t *testing.T) {
 		res, err := client.Request(ctx, "GET", "/api/v2/debug/health", nil)
 		require.NoError(t, err)
 		defer res.Body.Close()
-		_, _ = io.ReadAll(res.Body)
+		close(done)
+		bs, err := io.ReadAll(res.Body)
+		require.NoError(t, err, "reading body")
 		require.Equal(t, http.StatusServiceUnavailable, res.StatusCode)
+		var sdkResp codersdk.Response
+		require.NoError(t, json.Unmarshal(bs, &sdkResp), "unmarshaling sdk response")
+		require.Equal(t, "Healthcheck timed out.", sdkResp.Message)
+		require.Contains(t, sdkResp.Detail, "Still running: test (elapsed:")
 	})
 
 	t.Run("Refresh", func(t *testing.T) {
@@ -128,7 +131,7 @@ func TestDebugHealth(t *testing.T) {
 			ctx, cancel = context.WithTimeout(context.Background(), testutil.WaitShort)
 			client      = coderdtest.New(t, &coderdtest.Options{
 				HealthcheckRefresh: time.Microsecond,
-				HealthcheckFunc: func(context.Context, string) *healthsdk.HealthcheckReport {
+				HealthcheckFunc: func(context.Context, string, *healthcheck.Progress) *healthsdk.HealthcheckReport {
 					calls <- struct{}{}
 					return &healthsdk.HealthcheckReport{}
 				},
@@ -173,7 +176,7 @@ func TestDebugHealth(t *testing.T) {
 			client      = coderdtest.New(t, &coderdtest.Options{
 				HealthcheckRefresh: time.Hour,
 				HealthcheckTimeout: time.Hour,
-				HealthcheckFunc: func(context.Context, string) *healthsdk.HealthcheckReport {
+				HealthcheckFunc: func(context.Context, string, *healthcheck.Progress) *healthsdk.HealthcheckReport {
 					calls++
 					return &healthsdk.HealthcheckReport{
 						Time: time.Now(),
@@ -207,7 +210,7 @@ func TestDebugHealth(t *testing.T) {
 			ctx, cancel  = context.WithTimeout(context.Background(), testutil.WaitShort)
 			sessionToken string
 			client       = coderdtest.New(t, &coderdtest.Options{
-				HealthcheckFunc: func(_ context.Context, apiKey string) *healthsdk.HealthcheckReport {
+				HealthcheckFunc: func(_ context.Context, apiKey string, _ *healthcheck.Progress) *healthsdk.HealthcheckReport {
 					assert.Equal(t, sessionToken, apiKey)
 					return &healthsdk.HealthcheckReport{
 						Time:    time.Now(),

coderd/healthcheck/healthcheck.go

@@ -2,6 +2,9 @@ package healthcheck
 
 import (
 	"context"
+	"fmt"
+	"slices"
+	"strings"
 	"sync"
 	"time"
 
@@ -10,8 +13,91 @@ import (
 	"github.com/coder/coder/v2/coderd/healthcheck/health"
 	"github.com/coder/coder/v2/coderd/util/ptr"
 	"github.com/coder/coder/v2/codersdk/healthsdk"
+	"github.com/coder/quartz"
 )
 
+// Progress tracks the progress of healthcheck components for timeout
+// diagnostics. It records which checks have started and completed, along with
+// their durations, to provide useful information when a healthcheck times out.
+// The zero value is usable.
+type Progress struct {
+	Clock  quartz.Clock
+	mu     sync.Mutex
+	checks map[string]*checkStatus
+}
+
+type checkStatus struct {
+	startedAt   time.Time
+	completedAt time.Time
+}
+
+// Start records that a check has started.
+func (p *Progress) Start(name string) {
+	p.mu.Lock()
+	defer p.mu.Unlock()
+	if p.Clock == nil {
+		p.Clock = quartz.NewReal()
+	}
+	if p.checks == nil {
+		p.checks = make(map[string]*checkStatus)
+	}
+	p.checks[name] = &checkStatus{startedAt: p.Clock.Now()}
+}
+
+// Complete records that a check has finished.
+func (p *Progress) Complete(name string) {
+	p.mu.Lock()
+	defer p.mu.Unlock()
+	if p.Clock == nil {
+		p.Clock = quartz.NewReal()
+	}
+	if p.checks == nil {
+		p.checks = make(map[string]*checkStatus)
+	}
+	if p.checks[name] == nil {
+		p.checks[name] = &checkStatus{startedAt: p.Clock.Now()}
+	}
+	p.checks[name].completedAt = p.Clock.Now()
+}
+
+// Reset clears all recorded check statuses.
+func (p *Progress) Reset() {
+	p.mu.Lock()
+	defer p.mu.Unlock()
+	p.checks = make(map[string]*checkStatus)
+}
+
+// Summary returns a human-readable summary of check progress.
+// Example: "Completed: AccessURL (95ms), Database (120ms). Still running: DERP, Websocket"
+func (p *Progress) Summary() string {
+	p.mu.Lock()
+	defer p.mu.Unlock()
+
+	var completed, running []string
+	for name, status := range p.checks {
+		if status.completedAt.IsZero() {
+			elapsed := p.Clock.Now().Sub(status.startedAt).Round(time.Millisecond)
+			running = append(running, fmt.Sprintf("%s (elapsed: %dms)", name, elapsed.Milliseconds()))
+			continue
+		}
+		duration := status.completedAt.Sub(status.startedAt).Round(time.Millisecond)
+		completed = append(completed, fmt.Sprintf("%s (%dms)", name, duration.Milliseconds()))
+	}
+
+	// Sort for consistent output.
+	slices.Sort(completed)
+	slices.Sort(running)
+
+	var parts []string
+	if len(completed) > 0 {
+		parts = append(parts, "Completed: "+strings.Join(completed, ", "))
+	}
+	if len(running) > 0 {
+		parts = append(parts, "Still running: "+strings.Join(running, ", "))
+	}
+	return strings.Join(parts, ". ")
+}
+
 type Checker interface {
 	DERP(ctx context.Context, opts *derphealth.ReportOptions) healthsdk.DERPHealthReport
 	AccessURL(ctx context.Context, opts *AccessURLReportOptions) healthsdk.AccessURLReport
@@ -30,6 +116,10 @@ type ReportOptions struct {
 	ProvisionerDaemons ProvisionerDaemonsReportDeps
 
 	Checker Checker
+
+	// Progress tracks healthcheck progress for timeout diagnostics.
+	// If set, each check will record its start and completion time.
+	Progress *Progress
 }
 
 type defaultChecker struct{}
@@ -89,6 +179,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("DERP")
+			defer opts.Progress.Complete("DERP")
+		}
 		report.DERP = opts.Checker.DERP(ctx, &opts.DerpHealth)
 	}()
 
@@ -101,6 +195,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("AccessURL")
+			defer opts.Progress.Complete("AccessURL")
+		}
 		report.AccessURL = opts.Checker.AccessURL(ctx, &opts.AccessURL)
 	}()
 
@@ -113,6 +211,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("Websocket")
+			defer opts.Progress.Complete("Websocket")
+		}
 		report.Websocket = opts.Checker.Websocket(ctx, &opts.Websocket)
 	}()
 
@@ -125,6 +227,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("Database")
+			defer opts.Progress.Complete("Database")
+		}
 		report.Database = opts.Checker.Database(ctx, &opts.Database)
 	}()
 
@@ -137,6 +243,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("WorkspaceProxy")
+			defer opts.Progress.Complete("WorkspaceProxy")
+		}
 		report.WorkspaceProxy = opts.Checker.WorkspaceProxy(ctx, &opts.WorkspaceProxy)
 	}()
 
@@ -149,6 +259,10 @@ func Run(ctx context.Context, opts *ReportOptions) *healthsdk.HealthcheckReport
 			}
 		}()
 
+		if opts.Progress != nil {
+			opts.Progress.Start("ProvisionerDaemons")
+			defer opts.Progress.Complete("ProvisionerDaemons")
+		}
 		report.ProvisionerDaemons = opts.Checker.ProvisionerDaemons(ctx, &opts.ProvisionerDaemons)
 	}()
 

coderd/healthcheck/healthcheck_test.go

@@ -3,6 +3,7 @@ package healthcheck_test
 import (
 	"context"
 	"testing"
+	"time"
 
 	"github.com/stretchr/testify/assert"
 
@@ -10,6 +11,7 @@ import (
 	"github.com/coder/coder/v2/coderd/healthcheck/derphealth"
 	"github.com/coder/coder/v2/coderd/healthcheck/health"
 	"github.com/coder/coder/v2/codersdk/healthsdk"
+	"github.com/coder/quartz"
 )
 
 type testChecker struct {
@@ -533,3 +535,69 @@ func TestHealthcheck(t *testing.T) {
 		})
 	}
 }
+
+func TestCheckProgress(t *testing.T) {
+	t.Parallel()
+
+	t.Run("Summary", func(t *testing.T) {
+		t.Parallel()
+
+		mClock := quartz.NewMock(t)
+		progress := healthcheck.Progress{Clock: mClock}
+
+		// Start some checks
+		progress.Start("Database")
+		progress.Start("DERP")
+		progress.Start("AccessURL")
+
+		// Advance time to simulate check duration
+		mClock.Advance(100 * time.Millisecond)
+
+		// Complete some checks
+		progress.Complete("Database")
+		progress.Complete("AccessURL")
+
+		summary := progress.Summary()
+
+		// Verify completed and running checks are listed with duration / elapsed
+		assert.Equal(t, summary, "Completed: AccessURL (100ms), Database (100ms). Still running: DERP (elapsed: 100ms)")
+	})
+
+	t.Run("EmptyProgress", func(t *testing.T) {
+		t.Parallel()
+
+		mClock := quartz.NewMock(t)
+		progress := healthcheck.Progress{Clock: mClock}
+		summary := progress.Summary()
+
+		// Should be empty string when nothing tracked
+		assert.Empty(t, summary)
+	})
+
+	t.Run("AllCompleted", func(t *testing.T) {
+		t.Parallel()
+
+		mClock := quartz.NewMock(t)
+		progress := healthcheck.Progress{Clock: mClock}
+		progress.Start("Database")
+		progress.Start("DERP")
+		mClock.Advance(50 * time.Millisecond)
+		progress.Complete("Database")
+		progress.Complete("DERP")
+
+		summary := progress.Summary()
+		assert.Equal(t, summary, "Completed: DERP (50ms), Database (50ms)")
+	})
+
+	t.Run("AllRunning", func(t *testing.T) {
+		t.Parallel()
+
+		mClock := quartz.NewMock(t)
+		progress := healthcheck.Progress{Clock: mClock}
+		progress.Start("Database")
+		progress.Start("DERP")
+
+		summary := progress.Summary()
+		assert.Equal(t, summary, "Still running: DERP (elapsed: 0ms), Database (elapsed: 0ms)")
+	})
+}

coderd/httpapi/httpapi.go

@@ -493,16 +493,10 @@ func OneWayWebSocketEventSender(rw http.ResponseWriter, r *http.Request) (
 	return sendEvent, closed, nil
 }
 
-// OAuth2Error represents an OAuth2-compliant error response per RFC 6749.
-type OAuth2Error struct {
-	Error            string `json:"error"`
-	ErrorDescription string `json:"error_description,omitempty"`
-}
-
 // WriteOAuth2Error writes an OAuth2-compliant error response per RFC 6749.
 // This should be used for all OAuth2 endpoints (/oauth2/*) to ensure compliance.
-func WriteOAuth2Error(ctx context.Context, rw http.ResponseWriter, status int, errorCode, description string) {
-	Write(ctx, rw, status, OAuth2Error{
+func WriteOAuth2Error(ctx context.Context, rw http.ResponseWriter, status int, errorCode codersdk.OAuth2ErrorCode, description string) {
+	Write(ctx, rw, status, codersdk.OAuth2Error{
 		Error:            errorCode,
 		ErrorDescription: description,
 	})

coderd/httpmw/httproute.go

@@ -0,0 +1,71 @@
+package httpmw
+
+import (
+	"context"
+	"net/http"
+	"strings"
+
+	"github.com/go-chi/chi/v5"
+)
+
+type (
+	httpRouteInfoKey struct{}
+)
+
+type httpRouteInfo struct {
+	Route  string
+	Method string
+}
+
+// ExtractHTTPRoute retrieves just the HTTP route pattern from context.
+// Returns empty string if not set.
+func ExtractHTTPRoute(ctx context.Context) string {
+	ri, _ := ctx.Value(httpRouteInfoKey{}).(httpRouteInfo)
+	return ri.Route
+}
+
+// ExtractHTTPMethod retrieves just the HTTP method from context.
+// Returns empty string if not set.
+func ExtractHTTPMethod(ctx context.Context) string {
+	ri, _ := ctx.Value(httpRouteInfoKey{}).(httpRouteInfo)
+	return ri.Method
+}
+
+// HTTPRoute is middleware that stores the HTTP route pattern and method in
+// context for use by downstream handlers and services (e.g. prometheus).
+func HTTPRoute(next http.Handler) http.Handler {
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		route := getRoutePattern(r)
+		ctx := context.WithValue(r.Context(), httpRouteInfoKey{}, httpRouteInfo{
+			Route:  route,
+			Method: r.Method,
+		})
+		next.ServeHTTP(w, r.WithContext(ctx))
+	})
+}
+
+func getRoutePattern(r *http.Request) string {
+	rctx := chi.RouteContext(r.Context())
+	if rctx == nil {
+		return ""
+	}
+
+	routePath := r.URL.Path
+	if r.URL.RawPath != "" {
+		routePath = r.URL.RawPath
+	}
+
+	tctx := chi.NewRouteContext()
+	routes := rctx.Routes
+	if routes != nil && !routes.Match(tctx, r.Method, routePath) {
+		// No matching pattern. /api/* requests will be matched as "UNKNOWN"
+		// All other ones will be matched as "STATIC".
+		if strings.HasPrefix(routePath, "/api/") {
+			return "UNKNOWN"
+		}
+		return "STATIC"
+	}
+
+	// tctx has the updated pattern, since Match mutates it
+	return tctx.RoutePattern()
+}

coderd/httpmw/httproute_test.go

@@ -0,0 +1,104 @@
+package httpmw_test
+
+import (
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/go-chi/chi/v5"
+	"github.com/stretchr/testify/assert"
+
+	"github.com/coder/coder/v2/coderd/httpmw"
+	"github.com/coder/coder/v2/testutil"
+)
+
+func TestHTTPRoute(t *testing.T) {
+	t.Parallel()
+
+	for _, tc := range []struct {
+		name           string
+		reqFn          func() *http.Request
+		registerRoutes map[string]string
+		mws            []func(http.Handler) http.Handler
+		expectedRoute  string
+		expectedMethod string
+	}{
+		{
+			name: "without middleware",
+			reqFn: func() *http.Request {
+				return httptest.NewRequest(http.MethodGet, "/", nil)
+			},
+			registerRoutes: map[string]string{http.MethodGet: "/"},
+			mws:            []func(http.Handler) http.Handler{},
+			expectedRoute:  "",
+			expectedMethod: "",
+		},
+		{
+			name: "root",
+			reqFn: func() *http.Request {
+				return httptest.NewRequest(http.MethodGet, "/", nil)
+			},
+			registerRoutes: map[string]string{http.MethodGet: "/"},
+			mws:            []func(http.Handler) http.Handler{httpmw.HTTPRoute},
+			expectedRoute:  "/",
+			expectedMethod: http.MethodGet,
+		},
+		{
+			name: "parameterized route",
+			reqFn: func() *http.Request {
+				return httptest.NewRequest(http.MethodPut, "/users/123", nil)
+			},
+			registerRoutes: map[string]string{http.MethodPut: "/users/{id}"},
+			mws:            []func(http.Handler) http.Handler{httpmw.HTTPRoute},
+			expectedRoute:  "/users/{id}",
+			expectedMethod: http.MethodPut,
+		},
+		{
+			name: "unknown",
+			reqFn: func() *http.Request {
+				return httptest.NewRequest(http.MethodGet, "/api/a", nil)
+			},
+			registerRoutes: map[string]string{http.MethodGet: "/api/b"},
+			mws:            []func(http.Handler) http.Handler{httpmw.HTTPRoute},
+			expectedRoute:  "UNKNOWN",
+			expectedMethod: http.MethodGet,
+		},
+		{
+			name: "static",
+			reqFn: func() *http.Request {
+				return httptest.NewRequest(http.MethodGet, "/some/static/file.png", nil)
+			},
+			registerRoutes: map[string]string{http.MethodGet: "/"},
+			mws:            []func(http.Handler) http.Handler{httpmw.HTTPRoute},
+			expectedRoute:  "STATIC",
+			expectedMethod: http.MethodGet,
+		},
+	} {
+		t.Run(tc.name, func(t *testing.T) {
+			t.Parallel()
+
+			ctx := testutil.Context(t, testutil.WaitShort)
+			r := chi.NewRouter()
+			done := make(chan string)
+			for _, mw := range tc.mws {
+				r.Use(mw)
+			}
+			r.Use(func(next http.Handler) http.Handler {
+				return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+					defer close(done)
+					method := httpmw.ExtractHTTPMethod(r.Context())
+					route := httpmw.ExtractHTTPRoute(r.Context())
+					assert.Equal(t, tc.expectedMethod, method, "expected method mismatch")
+					assert.Equal(t, tc.expectedRoute, route, "expected route mismatch")
+					next.ServeHTTP(w, r)
+				})
+			})
+			for method, route := range tc.registerRoutes {
+				r.MethodFunc(method, route, func(w http.ResponseWriter, r *http.Request) {})
+			}
+			req := tc.reqFn()
+			r.ServeHTTP(httptest.NewRecorder(), req)
+			_ = testutil.TryReceive(ctx, t, done)
+		})
+	}
+}

coderd/httpmw/oauth2.go

@@ -290,15 +290,15 @@ func (*codersdkErrorWriter) writeClientNotFound(ctx context.Context, rw http.Res
 type oauth2ErrorWriter struct{}
 
 func (*oauth2ErrorWriter) writeMissingClientID(ctx context.Context, rw http.ResponseWriter) {
-	httpapi.WriteOAuth2Error(ctx, rw, http.StatusBadRequest, "invalid_request", "Missing client_id parameter")
+	httpapi.WriteOAuth2Error(ctx, rw, http.StatusBadRequest, codersdk.OAuth2ErrorCodeInvalidRequest, "Missing client_id parameter")
 }
 
 func (*oauth2ErrorWriter) writeInvalidClientID(ctx context.Context, rw http.ResponseWriter, _ error) {
-	httpapi.WriteOAuth2Error(ctx, rw, http.StatusUnauthorized, "invalid_client", "The client credentials are invalid")
+	httpapi.WriteOAuth2Error(ctx, rw, http.StatusUnauthorized, codersdk.OAuth2ErrorCodeInvalidClient, "The client credentials are invalid")
 }
 
 func (*oauth2ErrorWriter) writeClientNotFound(ctx context.Context, rw http.ResponseWriter) {
-	httpapi.WriteOAuth2Error(ctx, rw, http.StatusUnauthorized, "invalid_client", "The client credentials are invalid")
+	httpapi.WriteOAuth2Error(ctx, rw, http.StatusUnauthorized, codersdk.OAuth2ErrorCodeInvalidClient, "The client credentials are invalid")
 }
 
 // extractOAuth2ProviderAppBase is the internal implementation that uses the strategy pattern

coderd/httpmw/prometheus.go

@@ -3,10 +3,8 @@ package httpmw
 import (
 	"net/http"
 	"strconv"
-	"strings"
 	"time"
 
-	"github.com/go-chi/chi/v5"
 	"github.com/prometheus/client_golang/prometheus"
 	"github.com/prometheus/client_golang/prometheus/promauto"
 
@@ -71,7 +69,7 @@ func Prometheus(register prometheus.Registerer) func(http.Handler) http.Handler
 			var (
 				dist     *prometheus.HistogramVec
 				distOpts []string
-				path     = getRoutePattern(r)
+				path     = ExtractHTTPRoute(r.Context())
 			)
 
 			// We want to count WebSockets separately.
@@ -98,29 +96,3 @@ func Prometheus(register prometheus.Registerer) func(http.Handler) http.Handler
 		})
 	}
 }
-
-func getRoutePattern(r *http.Request) string {
-	rctx := chi.RouteContext(r.Context())
-	if rctx == nil {
-		return ""
-	}
-
-	routePath := r.URL.Path
-	if r.URL.RawPath != "" {
-		routePath = r.URL.RawPath
-	}
-
-	tctx := chi.NewRouteContext()
-	routes := rctx.Routes
-	if routes != nil && !routes.Match(tctx, r.Method, routePath) {
-		// No matching pattern. /api/* requests will be matched as "UNKNOWN"
-		// All other ones will be matched as "STATIC".
-		if strings.HasPrefix(routePath, "/api/") {
-			return "UNKNOWN"
-		}
-		return "STATIC"
-	}
-
-	// tctx has the updated pattern, since Match mutates it
-	return tctx.RoutePattern()
-}

coderd/httpmw/prometheus_test.go

@@ -29,9 +29,9 @@ func TestPrometheus(t *testing.T) {
 		req = req.WithContext(context.WithValue(req.Context(), chi.RouteCtxKey, chi.NewRouteContext()))
 		res := &tracing.StatusWriter{ResponseWriter: httptest.NewRecorder()}
 		reg := prometheus.NewRegistry()
-		httpmw.Prometheus(reg)(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		httpmw.HTTPRoute(httpmw.Prometheus(reg)(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 			w.WriteHeader(http.StatusOK)
-		})).ServeHTTP(res, req)
+		}))).ServeHTTP(res, req)
 		metrics, err := reg.Gather()
 		require.NoError(t, err)
 		require.Greater(t, len(metrics), 0)
@@ -57,7 +57,7 @@ func TestPrometheus(t *testing.T) {
 		wrappedHandler := promMW(testHandler)
 
 		r := chi.NewRouter()
-		r.Use(tracing.StatusWriterMiddleware, promMW)
+		r.Use(tracing.StatusWriterMiddleware, httpmw.HTTPRoute, promMW)
 		r.Get("/api/v2/build/{build}/logs", func(rw http.ResponseWriter, r *http.Request) {
 			wrappedHandler.ServeHTTP(rw, r)
 		})
@@ -85,7 +85,7 @@ func TestPrometheus(t *testing.T) {
 		promMW := httpmw.Prometheus(reg)
 
 		r := chi.NewRouter()
-		r.With(promMW).Get("/api/v2/users/{user}", func(w http.ResponseWriter, r *http.Request) {})
+		r.With(httpmw.HTTPRoute).With(promMW).Get("/api/v2/users/{user}", func(w http.ResponseWriter, r *http.Request) {})
 
 		req := httptest.NewRequest("GET", "/api/v2/users/john", nil)
 
@@ -115,6 +115,7 @@ func TestPrometheus(t *testing.T) {
 		promMW := httpmw.Prometheus(reg)
 
 		r := chi.NewRouter()
+		r.Use(httpmw.HTTPRoute)
 		r.Use(promMW)
 		r.NotFound(func(w http.ResponseWriter, r *http.Request) {
 			w.WriteHeader(http.StatusNotFound)
@@ -145,6 +146,7 @@ func TestPrometheus(t *testing.T) {
 		promMW := httpmw.Prometheus(reg)
 
 		r := chi.NewRouter()
+		r.Use(httpmw.HTTPRoute)
 		r.Use(promMW)
 		r.NotFound(func(w http.ResponseWriter, r *http.Request) {
 			w.WriteHeader(http.StatusNotFound)
@@ -173,6 +175,7 @@ func TestPrometheus(t *testing.T) {
 		promMW := httpmw.Prometheus(reg)
 
 		r := chi.NewRouter()
+		r.Use(httpmw.HTTPRoute)
 		r.Use(promMW)
 		r.Get("/api/v2/workspaceagents/{workspaceagent}/pty", func(w http.ResponseWriter, r *http.Request) {})