fi stop tracing 4xx http status codes as errors (#3707 )

CLI: coder licensese delete (#3699 )
Signed-off-by: Spike Curtis <spike@coder.com> Signed-off-by: Spike Curtis <spike@coder.com>
2022-08-26 15:18:42 +00:00 · 2022-08-26 08:15:46 -07:00 · 2022-08-26 17:52:25 +03:00 · 2022-08-26 17:38:40 +03:00 · 2022-08-26 12:28:38 +03:00 · 2022-08-25 19:20:31 -04:00
4590 changed files with 41323 additions and 13811 deletions
@@ -7,7 +7,7 @@ trim_trailing_whitespace = true
 insert_final_newline = true
 indent_style = tab

-[*.{md,json,yaml,tf,tfvars}]
+[*.{md,json,yaml,yml,tf,tfvars}]
 indent_style = space
 indent_size = 2

@@ -1 +1,2 @@
 site/ @coder/frontend
+docs/ @ammario
@@ -9,14 +9,17 @@ github_checks:
  annotations: false

 coverage:
+  range: 50..75
+  round: down
+  precision: 2
  status:
    patch:
      default:
        informational: yes
    project:
      default:
-        target: 70%
-        informational: yes
+        target: 65%
+        informational: true

 ignore:
  # This is generated code.
@@ -34,3 +37,7 @@ ignore:
  - scripts
  - site/.storybook
  - rules.go
+  # Packages used for writing tests.
+  - cli/clitest
+  - coderd/coderdtest
+  - pty/ptytest
@@ -3,7 +3,7 @@ updates:
  - package-ecosystem: "github-actions"
    directory: "/"
    schedule:
-      interval: "weekly"
+      interval: "monthly"
      time: "06:00"
      timezone: "America/Chicago"
    labels: []
@@ -28,23 +28,32 @@ updates:
  - package-ecosystem: "gomod"
    directory: "/"
    schedule:
-      interval: "weekly"
-      time: "06:00"
-      timezone: "America/Chicago"
-    commit-message:
-      prefix: "chore"
-    labels: []
-
-  - package-ecosystem: "npm"
-    directory: "/site/"
-    schedule:
-      interval: "weekly"
+      interval: "monthly"
      time: "06:00"
      timezone: "America/Chicago"
    commit-message:
      prefix: "chore"
    labels: []
    ignore:
+      # Ignore patch updates for all dependencies
+      - dependency-name: "*"
+        update-types:
+        - version-update:semver-patch
+
+  - package-ecosystem: "npm"
+    directory: "/site/"
+    schedule:
+      interval: "monthly"
+      time: "06:00"
+      timezone: "America/Chicago"
+    commit-message:
+      prefix: "chore"
+    labels: []
+    ignore:
+      # Ignore patch updates for all dependencies
+      - dependency-name: "*"
+        update-types:
+        - version-update:semver-patch
      # Ignore major updates to Node.js types, because they need to
      # correspond to the Node.js engine version
      - dependency-name: "@types/node"
@@ -54,7 +63,7 @@ updates:
  - package-ecosystem: "terraform"
    directory: "/examples/templates"
    schedule:
-      interval: "weekly"
+      interval: "monthly"
      time: "06:00"
      timezone: "America/Chicago"
    commit-message:
@@ -1,12 +0,0 @@
-# Number of days of inactivity before an issue becomes stale
-daysUntilStale: 60
-# Number of days of inactivity before a stale issue is closed
-daysUntilClose: 7
-# Label to apply when stale.
-staleLabel: stale
-# Comment to post when marking an issue as stale. Set to `false` to disable
-markComment: >
-  This issue has been automatically marked as stale because it has not had
-  recent activity. It will be closed if no activity occurs in the next 5 days.
-# Comment to post when closing a stale issue. Set to `false` to disable
-closeComment: false
@@ -1,68 +0,0 @@
-# Note: Chromatic is a separate workflow for coder.yaml as suggested by the
-# chromatic docs. Explicitly, Chromatic works best on 'push' instead of other
-# event types (like pull request), keep in mind that it works build-over-build
-# by storing snapshots.
-#
-# SEE: https://www.chromatic.com/docs/ci
-name: chromatic
-
-# REMARK: We want Chromatic to run whenever anything in the FE or its deps
-#         change, including node_modules and generated code. Currently, all
-#         node_modules and generated code live in site. If any of these are
-#         hoisted, we'll want to adjust the paths filter to account for them.
-on:
-  push:
-    paths:
-      - site/**
-    branches:
-      - main
-    tags:
-      - "*"
-
-  pull_request:
-    paths:
-      - site/**
-
-jobs:
-  deploy:
-    # REMARK: this is only used to build storybook and deploy it to Chromatic.
-    runs-on: ubuntu-latest
-
-    steps:
-      - uses: actions/checkout@v3
-        with:
-          # Required by Chromatic for build-over-build history, otherwise we
-          # only get 1 commit on shallow checkout.
-          fetch-depth: 0
-
-      - name: Install dependencies
-        run: cd site && yarn
-
-      # This step is not meant for mainline because any detected changes to
-      # storybook snapshots will require manual approval/review in order for
-      # the check to pass. This is desired in PRs, but not in mainline.
-      - name: Publish to Chromatic (non-mainline)
-        if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@v1
-        with:
-          buildScriptName: "storybook:build"
-          exitOnceUploaded: true
-          # Chromatic states its fine to make this token public. See:
-          # https://www.chromatic.com/docs/github-actions#forked-repositories
-          projectToken: 695c25b6cb65
-          workingDir: "./site"
-
-      # This is a separate step for mainline only that auto accepts and changes
-      # instead of holding CI up. Since we squash/merge, this is defensive to
-      # avoid the same changeset from requiring review once squashed into
-      # main. Chromatic is supposed to be able to detect that we use squash
-      # commits, but it's good to be defensive in case, otherwise CI remains
-      # infinitely "in progress" in mainline unless we re-review each build.
-      - name: Publish to Chromatic (mainline)
-        if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
-        uses: chromaui/action@v1
-        with:
-          autoAcceptChanges: true
-          buildScriptName: "storybook:build"
-          projectToken: 695c25b6cb65
-          workingDir: "./site"
@@ -30,6 +30,64 @@ concurrency:
  cancel-in-progress: ${{ github.event_name == 'pull_request' }}

 jobs:
+  typos:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v2
+      - name: typos-action
+        uses: crate-ci/typos@master
+        with:
+          config: .github/workflows/typos.toml
+      - name: Fix Helper
+        if: ${{ failure() }}
+        run: |
+          echo "::notice:: you can automatically fix typos from your CLI:
+          cargo install typos-cli
+          typos -c .github/workflows/typos.toml -w"
+
+  changes:
+    runs-on: ubuntu-latest
+    outputs:
+      docs-only: ${{ steps.filter.outputs.docs_count == steps.filter.outputs.all_count }}
+      sh: ${{ steps.filter.outputs.sh }}
+      ts: ${{ steps.filter.outputs.ts }}
+      k8s: ${{ steps.filter.outputs.k8s }}
+    steps:
+      - uses: actions/checkout@v3
+      # For pull requests it's not necessary to checkout the code
+      - uses: dorny/paths-filter@v2
+        id: filter
+        with:
+          filters: |
+            all:
+              - '**'
+            docs:
+              - 'docs/**'
+              # For testing:
+              # - '.github/**'
+            sh:
+              - "**.sh"
+            ts:
+              - 'site/**'
+            k8s:
+              - 'helm/**'
+              - Dockerfile
+              - scripts/helm.sh
+      - id: debug
+        run: |
+          echo "${{ toJSON(steps.filter )}}"
+
+  # Debug step
+  debug-inputs:
+    needs:
+      - changes
+    runs-on: ubuntu-latest
+    steps:
+      - id: log
+        run: |
+          echo "${{ toJSON(needs) }}"
+
  style-lint-golangci:
    name: style/lint/golangci
    timeout-minutes: 5
@@ -38,11 +96,20 @@ jobs:
      - uses: actions/checkout@v3
      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"
      - name: golangci-lint
        uses: golangci/golangci-lint-action@v3.2.0
        with:
-          version: v1.46.0
+          version: v1.48.0
+
+  check-enterprise-imports:
+    name: check/enterprise-imports
+    timeout-minutes: 5
+    runs-on: ubuntu-latest
+    steps:
+      - uses: actions/checkout@v3
+      - name: Check imports of enterprise code
+        run: ./scripts/check_enterprise_imports.sh

  style-lint-shellcheck:
    name: style/lint/shellcheck
@@ -83,10 +150,32 @@ jobs:
        run: yarn lint
        working-directory: site

+  style-lint-k8s:
+    name: "style/lint/k8s"
+    timeout-minutes: 5
+    needs: changes
+    if: needs.changes.outputs.k8s == 'true'
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+
+      - name: Install helm
+        uses: azure/setup-helm@v3
+        with:
+          version: v3.9.2
+
+      - name: cd helm && make lint
+        run: |
+          cd helm
+          make lint
+
  gen:
    name: "style/gen"
-    timeout-minutes: 5
+    timeout-minutes: 8
    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.docs-only == 'false'
    steps:
      - uses: actions/checkout@v3

@@ -110,15 +199,41 @@ jobs:
          version: "3.20.0"
      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
-      - run: |
-          curl -sSL https://github.com/kyleconroy/sqlc/releases/download/v1.13.0/sqlc_1.13.0_linux_amd64.tar.gz | sudo tar -C /usr/bin -xz sqlc
+          go-version: "~1.19"

-      - run: go install google.golang.org/protobuf/cmd/protoc-gen-go@v1.26
-      - run: go install storj.io/drpc/cmd/protoc-gen-go-drpc@v0.0.26
-      - run: go install golang.org/x/tools/cmd/goimports@latest
-      - run: "make --output-sync -j -B gen"
-      - run: ./scripts/check_unstaged.sh
+      - name: Echo Go Cache Paths
+        id: go-cache-paths
+        run: |
+          echo "::set-output name=go-build::$(go env GOCACHE)"
+          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+
+      - name: Go Build Cache
+        uses: actions/cache@v3
+        with:
+          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          key: ${{ github.job }}-go-build-${{ hashFiles('**/go.sum', '**/**.go') }}
+
+      - name: Go Mod Cache
+        uses: actions/cache@v3
+        with:
+          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          key: ${{ github.job }}-go-mod-${{ hashFiles('**/go.sum') }}
+
+      - name: Install sqlc
+        run: |
+          curl -sSL https://github.com/kyleconroy/sqlc/releases/download/v1.13.0/sqlc_1.13.0_linux_amd64.tar.gz | sudo tar -C /usr/bin -xz sqlc
+      - name: Install protoc-gen-go
+        run: go install google.golang.org/protobuf/cmd/protoc-gen-go@v1.26
+      - name: Install protoc-gen-go-drpc
+        run: go install storj.io/drpc/cmd/protoc-gen-go-drpc@v0.0.26
+      - name: Install goimports
+        run: go install golang.org/x/tools/cmd/goimports@latest
+
+      - name: make gen
+        run: "make --output-sync -j -B gen"
+
+      - name: Check for unstaged files
+        run: ./scripts/check_unstaged.sh

  style-fmt:
    name: "style/fmt"
@@ -148,7 +263,8 @@ jobs:
      - name: Install shfmt
        run: go install mvdan.cc/sh/v3/cmd/shfmt@v3.5.0

-      - run: |
+      - name: make fmt
+        run: |
          export PATH=${PATH}:$(go env GOPATH)/bin
          make --output-sync -j -B fmt

@@ -167,7 +283,7 @@ jobs:

      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"

      - name: Echo Go Cache Paths
        id: go-cache-paths
@@ -179,7 +295,7 @@ jobs:
        uses: actions/cache@v3
        with:
          path: ${{ steps.go-cache-paths.outputs.go-build }}
-          key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.sum') }}
+          key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.**', '**.go') }}

      - name: Go Mod Cache
        uses: actions/cache@v3
@@ -197,21 +313,31 @@ jobs:

      - uses: hashicorp/setup-terraform@v2
        with:
-          terraform_version: 1.1.2
+          terraform_version: 1.1.9
          terraform_wrapper: false

      - name: Test with Mock Database
+        id: test
        shell: bash
-        env:
-          GOCOUNT: ${{ runner.os == 'Windows' && 1 || 2 }}
-          GOMAXPROCS: ${{ runner.os == 'Windows' && 1 || 2 }}
-        run: gotestsum --junitfile="gotests.xml" --packages="./..." --
-          -covermode=atomic -coverprofile="gotests.coverage"
-          -coverpkg=./...,github.com/coder/coder/codersdk
-          -timeout=5m -count=$GOCOUNT -short -failfast
+        run: |
+          # Code coverage is more computationally expensive and also
+          # prevents test caching, so we disable it on alternate operating
+          # systems.
+          if [ "${{ matrix.os }}" == "ubuntu-latest" ]; then
+            echo ::set-output name=cover::true
+            export COVERAGE_FLAGS='-covermode=atomic -coverprofile="gotests.coverage" -coverpkg=./...'
+          else
+            echo ::set-output name=cover::false
+          fi
+          set -x
+          test_timeout=5m
+          if [[ "${{ matrix.os }}" == windows* ]]; then
+            test_timeout=10m
+          fi
+          gotestsum --junitfile="gotests.xml" --packages="./..." -- -parallel=8 -timeout=$test_timeout -short -failfast $COVERAGE_FLAGS

      - name: Upload DataDog Trace
-        if: always() && github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
+        if: github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
        env:
          DATADOG_API_KEY: ${{ secrets.DATADOG_API_KEY }}
          DD_DATABASE: fake
@@ -220,24 +346,31 @@ jobs:
        run: go run scripts/datadog-cireport/main.go gotests.xml

      - uses: codecov/codecov-action@v3
-        if: github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
+        # This action has a tendency to error out unexpectedly, it has
+        # the `fail_ci_if_error` option that defaults to `false`, but
+        # that is no guarantee, see:
+        # https://github.com/codecov/codecov-action/issues/788
+        continue-on-error: true
+        if: steps.test.outputs.cover && github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
        with:
          token: ${{ secrets.CODECOV_TOKEN }}
          files: ./gotests.coverage
          flags: unittest-go-${{ matrix.os }}
-          # this flakes and sometimes fails the build
-          fail_ci_if_error: false

  test-go-postgres:
    name: "test/go/postgres"
    runs-on: ubuntu-latest
-    timeout-minutes: 20
+    # This timeout must be greater than the timeout set by `go test` in
+    # `make test-postgres` to ensure we receive a trace of running
+    # goroutines. Setting this to the timeout +5m should work quite well
+    # even if some of the preceding steps are slow.
+    timeout-minutes: 25
    steps:
      - uses: actions/checkout@v3

      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"

      - name: Echo Go Cache Paths
        id: go-cache-paths
@@ -249,7 +382,7 @@ jobs:
        uses: actions/cache@v3
        with:
          path: ${{ steps.go-cache-paths.outputs.go-build }}
-          key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.sum') }}
+          key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.sum', '**/**.go') }}

      - name: Go Mod Cache
        uses: actions/cache@v3
@@ -267,33 +400,11 @@ jobs:

      - uses: hashicorp/setup-terraform@v2
        with:
-          terraform_version: 1.1.2
+          terraform_version: 1.1.9
          terraform_wrapper: false

-      - name: Start PostgreSQL Database
-        env:
-          POSTGRES_PASSWORD: postgres
-          POSTGRES_USER: postgres
-          POSTGRES_DB: postgres
-          PGDATA: /tmp
-        run: |
-          docker run \
-            -e POSTGRES_PASSWORD=postgres \
-            -e POSTGRES_USER=postgres \
-            -e POSTGRES_DB=postgres \
-            -e PGDATA=/tmp \
-            -p 5432:5432 \
-            -d postgres:11 \
-            -c shared_buffers=1GB \
-            -c max_connections=1000
-          while ! pg_isready -h 127.0.0.1
-          do
-              echo "$(date) - waiting for database to start"
-              sleep 0.5
-          done
-
      - name: Test with PostgreSQL Database
-        run: "make test-postgres"
+        run: make test-postgres

      - name: Upload DataDog Trace
        if: always() && github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
@@ -304,19 +415,25 @@ jobs:
        run: go run scripts/datadog-cireport/main.go gotests.xml

      - uses: codecov/codecov-action@v3
+        # This action has a tendency to error out unexpectedly, it has
+        # the `fail_ci_if_error` option that defaults to `false`, but
+        # that is no guarantee, see:
+        # https://github.com/codecov/codecov-action/issues/788
+        continue-on-error: true
        if: github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
        with:
          token: ${{ secrets.CODECOV_TOKEN }}
          files: ./gotests.coverage
          flags: unittest-go-postgres-${{ matrix.os }}
-          # this flakes and sometimes fails the build
-          fail_ci_if_error: false

  deploy:
    name: "deploy"
    runs-on: ubuntu-latest
    timeout-minutes: 30
-    if: github.ref == 'refs/heads/main' && !github.event.pull_request.head.repo.fork
+    needs: changes
+    if: |
+      github.ref == 'refs/heads/main' && !github.event.pull_request.head.repo.fork
+      && needs.changes.outputs.docs-only == 'false'
    permissions:
      contents: read
      id-token: write
@@ -336,7 +453,7 @@ jobs:

      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"

      - name: Echo Go Cache Paths
        id: go-cache-paths
@@ -370,6 +487,9 @@ jobs:
      - name: Install nfpm
        run: go install github.com/goreleaser/nfpm/v2/cmd/nfpm@v2.16.0

+      - name: Install zstd
+        run: sudo apt-get install -y zstd
+
      - name: Build site
        run: make -B site/out/index.html

@@ -382,6 +502,7 @@ jobs:
          # build slim binaries
          ./scripts/build_go_slim.sh \
            --output ./dist/ \
+            --compress 22 \
            linux:amd64,armv7,arm64 \
            windows:amd64,arm64 \
            darwin:amd64,arm64
@@ -390,7 +511,8 @@ jobs:
          ./scripts/build_go_matrix.sh \
            --output ./dist/ \
            --package-linux \
-            linux:amd64
+            linux:amd64 \
+            windows:amd64

      - name: Install Release
        run: |
@@ -408,6 +530,7 @@ jobs:
          name: coder
          path: |
            ./dist/*.zip
+            ./dist/*.exe
            ./dist/*.tar.gz
            ./dist/*.apk
            ./dist/*.deb
@@ -435,7 +558,7 @@ jobs:
      # Go is required for uploading the test results to datadog
      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"

      - uses: actions/setup-node@v3
        with:
@@ -448,13 +571,16 @@ jobs:
        working-directory: site

      - uses: codecov/codecov-action@v3
+        # This action has a tendency to error out unexpectedly, it has
+        # the `fail_ci_if_error` option that defaults to `false`, but
+        # that is no guarantee, see:
+        # https://github.com/codecov/codecov-action/issues/788
+        continue-on-error: true
        if: github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
        with:
          token: ${{ secrets.CODECOV_TOKEN }}
          files: ./site/coverage/lcov.info
          flags: unittest-js
-          # this flakes and sometimes fails the build
-          fail_ci_if_error: false

      - name: Upload DataDog Trace
        if: always() && github.actor != 'dependabot[bot]' && !github.event.pull_request.head.repo.fork
@@ -466,6 +592,9 @@ jobs:

  test-e2e:
    name: "test/e2e/${{ matrix.os }}"
+    needs:
+      - changes
+    if: needs.changes.outputs.docs-only == 'false'
    runs-on: ${{ matrix.os }}
    timeout-minutes: 20
    strategy:
@@ -482,18 +611,16 @@ jobs:
          path: |
            **/node_modules
            .eslintcache
-          key: js-${{ runner.os }}-test-${{ hashFiles('**/yarn.lock') }}
-          restore-keys: |
-            js-${{ runner.os }}-
+          key: js-${{ runner.os }}-e2e-${{ hashFiles('**/yarn.lock') }}

      # Go is required for uploading the test results to datadog
      - uses: actions/setup-go@v3
        with:
-          go-version: "~1.18"
+          go-version: "~1.19"

      - uses: hashicorp/setup-terraform@v2
        with:
-          terraform_version: 1.1.2
+          terraform_version: 1.1.9
          terraform_wrapper: false

      - uses: actions/setup-node@v3
@@ -520,6 +647,7 @@ jobs:

      - name: Build
        run: |
+          sudo npm install -g prettier
          make -B site/out/index.html

      - run: yarn playwright:install
@@ -533,6 +661,14 @@ jobs:
          DEBUG: pw:api
        working-directory: site

+      - name: Upload Playwright Failed Tests
+        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
+        uses: actions/upload-artifact@v3
+        with:
+          name: failed-test-videos
+          path: ./site/test-results/**/*.webm
+          retention:days: 7
+
      - name: Upload DataDog Trace
        if: always() && github.actor != 'dependabot[bot]' && runner.os == 'Linux' && !github.event.pull_request.head.repo.fork
        env:
@@ -540,3 +676,47 @@ jobs:
          DD_CATEGORY: e2e
          GIT_COMMIT_MESSAGE: ${{ github.event.head_commit.message }}
        run: go run scripts/datadog-cireport/main.go site/test-results/junit.xml
+  chromatic:
+    # REMARK: this is only used to build storybook and deploy it to Chromatic.
+    runs-on: ubuntu-latest
+    needs:
+      - changes
+    if: needs.changes.outputs.ts == 'true'
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          # Required by Chromatic for build-over-build history, otherwise we
+          # only get 1 commit on shallow checkout.
+          fetch-depth: 0
+
+      - name: Install dependencies
+        run: cd site && yarn
+
+      # This step is not meant for mainline because any detected changes to
+      # storybook snapshots will require manual approval/review in order for
+      # the check to pass. This is desired in PRs, but not in mainline.
+      - name: Publish to Chromatic (non-mainline)
+        if: github.ref != 'refs/heads/main' && github.repository_owner == 'coder'
+        uses: chromaui/action@v1
+        with:
+          buildScriptName: "storybook:build"
+          exitOnceUploaded: true
+          # Chromatic states its fine to make this token public. See:
+          # https://www.chromatic.com/docs/github-actions#forked-repositories
+          projectToken: 695c25b6cb65
+          workingDir: "./site"
+
+      # This is a separate step for mainline only that auto accepts and changes
+      # instead of holding CI up. Since we squash/merge, this is defensive to
+      # avoid the same changeset from requiring review once squashed into
+      # main. Chromatic is supposed to be able to detect that we use squash
+      # commits, but it's good to be defensive in case, otherwise CI remains
+      # infinitely "in progress" in mainline unless we re-review each build.
+      - name: Publish to Chromatic (mainline)
+        if: github.ref == 'refs/heads/main' && github.repository_owner == 'coder'
+        uses: chromaui/action@v1
+        with:
+          autoAcceptChanges: true
+          buildScriptName: "storybook:build"
+          projectToken: 695c25b6cb65
+          workingDir: "./site"
@@ -0,0 +1,51 @@
+name: dogfood
+
+on:
+  push:
+    branches:
+      - main
+    tags:
+      - "*"
+    paths:
+      - "dogfood/**"
+  pull_request:
+    paths:
+      - "dogfood/**"
+  workflow_dispatch:
+
+jobs:
+  deploy:
+    runs-on: ubuntu-latest
+    steps:
+      - name: Get branch name
+        id: branch-name
+        uses: tj-actions/branch-names@v5.4
+
+      - name: "Branch name to Docker tag name"
+        id: docker-tag-name
+        run: |
+          tag=${{ steps.branch-name.outputs.current_branch }}
+          # Replace / with --, e.g. user/feature => user--feature.
+          tag=${tag//\//--}
+          echo "::set-output name=tag::${tag}"
+
+      - name: Set up QEMU
+        uses: docker/setup-qemu-action@v2
+
+      - name: Set up Docker Buildx
+        uses: docker/setup-buildx-action@v2
+
+      - name: Login to DockerHub
+        uses: docker/login-action@v2
+        with:
+          username: ${{ secrets.DOCKERHUB_USERNAME }}
+          password: ${{ secrets.DOCKERHUB_PASSWORD }}
+
+      - name: Build and push
+        uses: docker/build-push-action@v3
+        with:
+          context: "{{defaultContext}}:dogfood"
+          push: true
+          tags: "codercom/oss-dogfood:${{ steps.docker-tag-name.outputs.tag }},codercom/oss-dogfood:latest"
+          cache-from: type=registry,ref=codercom/oss-dogfood:latest
+          cache-to: type=inline
@@ -68,6 +68,9 @@ jobs:
      - name: Install nfpm
        run: go install github.com/goreleaser/nfpm/v2/cmd/nfpm@v2.16.0

+      - name: Install zstd
+        run: sudo apt-get install -y zstd
+
      - name: Build Site
        run: make site/out/index.html

@@ -80,6 +83,7 @@ jobs:
          # build slim binaries
          ./scripts/build_go_slim.sh \
            --output ./dist/ \
+            --compress 22 \
            linux:amd64,armv7,arm64 \
            windows:amd64,arm64 \
            darwin:amd64,arm64
@@ -183,10 +187,10 @@ jobs:
      - name: Install dependencies
        run: |
          set -euo pipefail
-          # The version of bash that MacOS ships with is too old
+          # The version of bash that macOS ships with is too old
          brew install bash

-          # The version of make that MacOS ships with is too old
+          # The version of make that macOS ships with is too old
          brew install make
          echo "$(brew --prefix)/opt/make/libexec/gnubin" >> $GITHUB_PATH

@@ -198,6 +202,9 @@ jobs:
          brew tap mitchellh/gon
          brew install mitchellh/gon/gon

+          # Used for compressing embedded slim binaries
+          brew install zstd
+
      - name: Build Site
        run: make site/out/index.html

@@ -210,6 +217,7 @@ jobs:
          # build slim binaries
          ./scripts/build_go_slim.sh \
            --output ./dist/ \
+            --compress 22 \
            linux:amd64,armv7,arm64 \
            windows:amd64,arm64 \
            darwin:amd64,arm64
@@ -267,12 +275,19 @@ jobs:
      - name: ls artifacts
        run: ls artifacts

+      - name: Publish Helm
+        run: |
+          set -euxo pipefail
+          ./scripts/helm.sh --push
+          mv ./dist/*.tgz ./artifacts/
+
      - name: Publish Release
        run: |
          ./scripts/publish_release.sh \
            ${{ (github.event.inputs.dry_run || github.event.inputs.snapshot) && '--dry-run' }} \
            ./artifacts/*.zip \
            ./artifacts/*.tar.gz \
+            ./artifacts/*.tgz \
            ./artifacts/*.apk \
            ./artifacts/*.deb \
            ./artifacts/*.rpm
@@ -0,0 +1,35 @@
+name: Stale Issue Cron
+on:
+  schedule:
+    # Every day at midnight
+    - cron: "0 0 * * *"
+  workflow_dispatch:
+jobs:
+  stale:
+    runs-on: ubuntu-latest
+    permissions:
+      issues: write
+      pull-requests: write
+    steps:
+      # v5.1.0 has a weird bug that makes stalebot add then remove its own label
+      # https://github.com/actions/stale/pull/775
+      - uses: actions/stale@v5.0.0
+        with:
+          stale-issue-label: stale
+          stale-pr-label: stale
+          # Pull Requests become stale more quickly due to merge conflicts.
+          # Also, we promote minimizing WIP.
+          days-before-pr-stale: 7
+          days-before-pr-close: 3
+          stale-pr-message: >
+            This Pull Request is becoming stale. In order to minimize WIP, 
+            prevent merge conflicts and keep the tracker readable, I'm going
+            close to this PR in 3 days if there isn't more activity.
+          stale-issue-message: >
+            This issue is becoming stale. In order to keep the tracker readable
+            and actionable, I'm going close to this issue in 7 days if there 
+            isn't more activity.
+          # Upped from 30 since we have a big tracker and was hitting the limit.
+          operations-per-run: 60
+          # Start with the oldest issues, always.
+          ascending: true
@@ -0,0 +1,19 @@
+[default.extend-identifiers]
+alog = "alog"
+Jetbrains = "JetBrains"
+IST = "IST"
+MacOS = "macOS"
+
+[default.extend-words]
+
+[files]
+extend-exclude = [
+    "**.svg",
+    "**.png",
+    "**.lock",
+    "go.sum",
+    "go.mod",
+    # These files contain base64 strings that confuse the detector
+    "**XService**.ts",
+    "**identity.go",
+]
@@ -13,6 +13,7 @@ node_modules
 vendor
 .eslintcache
 yarn-error.log
+gotests.coverage
 .idea
 .DS_Store

@@ -33,9 +34,11 @@ dist/
 site/out/

 *.tfstate
+*.tfstate.backup
 *.tfplan
 *.lock.hcl
 .terraform/

 .vscode/*.log
 **/*.swp
+.coderv2/*
@@ -2,6 +2,7 @@
  "cSpell.words": [
    "apps",
    "awsidentity",
+    "bodyclose",
    "buildinfo",
    "buildname",
    "circbuf",
@@ -11,6 +12,7 @@
    "coderdtest",
    "codersdk",
    "cronstrue",
+    "databasefake",
    "devel",
    "drpc",
    "drpcconn",
@@ -36,12 +38,14 @@
    "Jobf",
    "Keygen",
    "kirsle",
+    "Kubernetes",
    "ldflags",
    "manifoldco",
    "mapstructure",
    "mattn",
    "mitchellh",
    "moby",
+    "namesgenerator",
    "nfpms",
    "nhooyr",
    "nolint",
@@ -49,8 +53,10 @@
    "ntqry",
    "OIDC",
    "oneof",
+    "paralleltest",
    "parameterscopeid",
    "pqtype",
+    "prometheusmetrics",
    "promptui",
    "protobuf",
    "provisionerd",
@@ -71,10 +77,12 @@
    "templateversions",
    "testdata",
    "testid",
+    "testutil",
    "tfexec",
    "tfjson",
    "tfplan",
    "tfstate",
+    "tparallel",
    "trimprefix",
    "turnconn",
    "typegen",
@@ -117,7 +125,9 @@
  "go.coverOnSave": true,
  // The codersdk is used by coderd another other packages extensively.
  // To reduce redundancy in tests, it's covered by other packages.
-  "go.testFlags": ["-short", "-coverpkg=./.,github.com/coder/coder/codersdk"],
+  // Since package coverage pairing can't be defined, all packages cover
+  // all other packages.
+  "go.testFlags": ["-short", "-coverpkg=./..."],
  "go.coverageDecorator": {
    "type": "gutter",
    "coveredHighlightColor": "rgba(64,128,128,0.5)",
@@ -1,4 +1,8 @@
-FROM alpine
+# This is the multi-arch Dockerfile used for Coder. Since it's multi-arch and
+# cross-compiled, it cannot have ANY "RUN" commands. All binaries are built
+# using the go toolchain on the host and then copied into the build context by
+# scripts/build_docker.sh.
+FROM alpine:latest

 # LABEL doesn't add any real layers so it's fine (and easier) to do it here than
 # in the build script.
@@ -12,6 +16,15 @@ LABEL \
 	org.opencontainers.image.licenses="AGPL-3.0"

 # The coder binary is injected by scripts/build_docker.sh.
-ADD coder /opt/coder
+COPY --chown=coder:coder --chmod=755 coder /opt/coder
+
+# Create coder group and user. We cannot use `addgroup` and `adduser` because
+# they won't work if we're building the image for a different architecture.
+COPY --chown=root:root --chmod=644 group passwd /etc/
+COPY --chown=coder:coder --chmod=700 empty-dir /home/coder
+
+USER coder:coder
+ENV HOME=/home/coder
+WORKDIR /home/coder

 ENTRYPOINT [ "/opt/coder", "server" ]
@@ -0,0 +1,9 @@
+LICENSE (GNU Affero General Public License) applies to
+all files in this repository, except for those in or under
+any directory named "enterprise", which are Copyright Coder
+Technologies, Inc., All Rights Reserved.
+
+We plan to release an enterprise license covering these files
+as soon as possible.  Watch this space.
+
+
@@ -20,7 +20,9 @@ bin: $(shell find . -not -path './vendor/*' -type f -name '*.go') go.mod go.sum

 	mkdir -p ./dist
 	rm -rf ./dist/coder-slim_*
+	rm -f ./site/out/bin/coder*
 	./scripts/build_go_slim.sh \
+		--compress 6 \
 		--version "$(VERSION)" \
 		--output ./dist/ \
 		linux:amd64,armv7,arm64 \
@@ -31,10 +33,12 @@ bin: $(shell find . -not -path './vendor/*' -type f -name '*.go') go.mod go.sum
 build: site/out/index.html $(shell find . -not -path './vendor/*' -type f -name '*.go') go.mod go.sum $(shell find ./examples/templates)
 	rm -rf ./dist
 	mkdir -p ./dist
+	rm -f ./site/out/bin/coder*

 	# build slim artifacts and copy them to the site output directory
 	./scripts/build_go_slim.sh \
 		--version "$(VERSION)" \
+		--compress 6 \
 		--output ./dist/ \
 		linux:amd64,armv7,arm64 \
 		windows:amd64,arm64 \
@@ -52,17 +56,13 @@ build: site/out/index.html $(shell find . -not -path './vendor/*' -type f -name
 .PHONY: build

 # Runs migrations to output a dump of the database.
-coderd/database/dump.sql: $(wildcard coderd/database/migrations/*.sql)
+coderd/database/dump.sql: coderd/database/dump/main.go $(wildcard coderd/database/migrations/*.sql)
 	go run coderd/database/dump/main.go

 # Generates Go code for querying the database.
-coderd/database/querier.go: coderd/database/dump.sql $(wildcard coderd/database/queries/*.sql)
+coderd/database/querier.go: coderd/database/sqlc.yaml coderd/database/dump.sql $(wildcard coderd/database/queries/*.sql)
 	coderd/database/generate.sh

-dev:
-	./scripts/develop.sh
-.PHONY: dev
-
 fmt/prettier:
 	@echo "--- prettier"
 	cd site
@@ -116,6 +116,7 @@ lint: lint/shellcheck lint/go
 .PHONY: lint

 lint/go:
+	./scripts/check_enterprise_imports.sh
 	golangci-lint run
 .PHONY: lint/go

@@ -166,14 +167,17 @@ test: test-clean
 	gotestsum -- -v -short ./...
 .PHONY: test

-test-postgres: test-clean
-	DB=ci gotestsum --junitfile="gotests.xml" --packages="./..." -- \
-          -covermode=atomic -coverprofile="gotests.coverage" -timeout=30m \
-          -coverpkg=./...,github.com/coder/coder/codersdk \
-          -count=1 -race -failfast
+# When updating -timeout for this test, keep in sync with
+# test-go-postgres (.github/workflows/coder.yaml).
+test-postgres: test-clean test-postgres-docker
+	DB=ci DB_FROM=$(shell go run scripts/migrate-ci/main.go) gotestsum --junitfile="gotests.xml" --packages="./..." -- \
+		-covermode=atomic -coverprofile="gotests.coverage" -timeout=20m \
+		-coverpkg=./... \
+		-count=1 -race -failfast
 .PHONY: test-postgres

 test-postgres-docker:
+	docker rm -f test-postgres-docker || true
 	docker run \
 		--env POSTGRES_PASSWORD=postgres \
 		--env POSTGRES_USER=postgres \
@@ -184,12 +188,17 @@ test-postgres-docker:
 		--name test-postgres-docker \
 		--restart no \
 		--detach \
-		postgres:11 \
+		postgres:13 \
 		-c shared_buffers=1GB \
 		-c max_connections=1000 \
 		-c fsync=off \
 		-c synchronous_commit=off \
 		-c full_page_writes=off
+	while ! pg_isready -h 127.0.0.1
+	do
+		echo "$(date) - waiting for database to start"
+		sleep 0.5
+	done
 .PHONY: test-postgres-docker

 test-clean:
@@ -1,12 +1,11 @@
 # Coder

-[!["GitHub
-Discussions"](https://img.shields.io/badge/%20GitHub-%20Discussions-gray.svg?longCache=true&logo=github&colorB=purple)](https://github.com/coder/coder/discussions)
 [!["Join us on
-Discord"](https://img.shields.io/badge/join-us%20on%20Discord-gray.svg?longCache=true&logo=discord&colorB=purple)](https://discord.gg/coder)
-[![Twitter
-Follow](https://img.shields.io/twitter/follow/CoderHQ?label=%40CoderHQ&style=social)](https://twitter.com/coderhq)
+Discord"](https://img.shields.io/badge/join-us%20on%20Discord-gray.svg?longCache=true&logo=discord&colorB=green)](https://discord.gg/coder)
 [![codecov](https://codecov.io/gh/coder/coder/branch/main/graph/badge.svg?token=TNLW3OAP6G)](https://codecov.io/gh/coder/coder)
+[![Go Reference](https://pkg.go.dev/badge/github.com/coder/coder.svg)](https://pkg.go.dev/github.com/coder/coder)
+[![Twitter
+Follow](https://img.shields.io/twitter/follow/coderhq?label=%40coderhq&style=social)](https://twitter.com/coderhq)

 Coder creates remote development machines so your team can develop from anywhere.

@@ -31,23 +30,31 @@ Coder creates remote development machines so your team can develop from anywhere
 ## Getting Started

 > **Note**:
-> Coder is in an alpha state. [Report issues here](https://github.com/coder/coder/issues/new).
+> Coder is in a beta state. [Report issues here](https://github.com/coder/coder/issues/new).

-There are a few ways to install Coder: [install script](https://coder.com/docs/coder-oss/latest/install#installsh) (macOS, Linux), [docker-compose](https://coder.com/docs/coder-oss/latest/install#docker-compose), or [manually](https://coder.com/docs/coder-oss/latest/install#manual) via the latest release (macOS, Windows, and Linux).
-
-If you use the install script, you can preview what occurs during the install process:
-
-```sh
-curl -fsSL https://coder.com/install.sh | sh -s -- --dry-run
-```
+The easiest way to install Coder is to use our [install script](https://github.com/coder/coder/blob/main/install.sh) for Linux and macOS.

 To install, run:

-```sh
-curl -fsSL https://coder.com/install.sh | sh
+```bash
+curl -L https://coder.com/install.sh | sh
 ```

-Once installed, you can start a production deployment with a single command:
+You can preview what occurs during the install process:
+
+```bash
+curl -L https://coder.com/install.sh | sh -s -- --dry-run
+```
+
+You can modify the installation process by including flags. Run the help command for reference:
+
+```bash
+curl -L https://coder.com/install.sh | sh -s -- --help
+```
+
+> See [install](docs/install.md) for additional methods.
+
+Once installed, you can start a production deployment<sup>1</sup> with a single command:

 ```sh
 # Automatically sets up an external access URL on *.try.coder.app
@@ -57,6 +64,8 @@ coder server --tunnel
 coder server --postgres-url <url> --access-url <url>
 ```

+> <sup>1</sup> The embedded database is great for trying out Coder with small deployments, but do consider using an external database for increased assurance and control.
+
 Use `coder --help` to get a complete list of flags and environment variables. Use our [quickstart guide](https://coder.com/docs/coder-oss/latest/quickstart) for a full walkthrough.

 ## Documentation
@@ -88,4 +97,4 @@ Join our community on [Discord](https://discord.gg/coder) and [Twitter](https://

 Read the [contributing docs](https://coder.com/docs/coder-oss/latest/CONTRIBUTING).

-Find our list of contributors [here](./docs/CONTRIBUTORS.md).
+Find our list of contributors [here](https://github.com/coder/coder/graphs/contributors).
@@ -27,10 +27,13 @@ import (
 	"go.uber.org/atomic"
 	gossh "golang.org/x/crypto/ssh"
 	"golang.org/x/xerrors"
+	"inet.af/netaddr"
+	"tailscale.com/types/key"

 	"cdr.dev/slog"
 	"github.com/coder/coder/agent/usershell"
 	"github.com/coder/coder/peer"
+	"github.com/coder/coder/peer/peerwg"
 	"github.com/coder/coder/peerbroker"
 	"github.com/coder/coder/pty"
 	"github.com/coder/retry"
@@ -40,23 +43,37 @@ const (
 	ProtocolReconnectingPTY = "reconnecting-pty"
 	ProtocolSSH             = "ssh"
 	ProtocolDial            = "dial"
+
+	// MagicSessionErrorCode indicates that something went wrong with the session, rather than the
+	// command just returning a nonzero exit code, and is chosen as an arbitrary, high number
+	// unlikely to shadow other exit codes, which are typically 1, 2, 3, etc.
+	MagicSessionErrorCode = 229
 )

 type Options struct {
+	EnableWireguard        bool
+	UploadWireguardKeys    UploadWireguardKeys
+	ListenWireguardPeers   ListenWireguardPeers
 	ReconnectingPTYTimeout time.Duration
 	EnvironmentVariables   map[string]string
 	Logger                 slog.Logger
 }

 type Metadata struct {
-	OwnerEmail           string            `json:"owner_email"`
-	OwnerUsername        string            `json:"owner_username"`
-	EnvironmentVariables map[string]string `json:"environment_variables"`
-	StartupScript        string            `json:"startup_script"`
-	Directory            string            `json:"directory"`
+	WireguardAddresses   []netaddr.IPPrefix `json:"addresses"`
+	EnvironmentVariables map[string]string  `json:"environment_variables"`
+	StartupScript        string             `json:"startup_script"`
+	Directory            string             `json:"directory"`
+}
+
+type WireguardPublicKeys struct {
+	Public key.NodePublic  `json:"public"`
+	Disco  key.DiscoPublic `json:"disco"`
 }

 type Dialer func(ctx context.Context, logger slog.Logger) (Metadata, *peerbroker.Listener, error)
+type UploadWireguardKeys func(ctx context.Context, keys WireguardPublicKeys) error
+type ListenWireguardPeers func(ctx context.Context, logger slog.Logger) (<-chan peerwg.Handshake, func(), error)

 func New(dialer Dialer, options *Options) io.Closer {
 	if options == nil {
@@ -73,6 +90,9 @@ func New(dialer Dialer, options *Options) io.Closer {
 		closeCancel:            cancelFunc,
 		closed:                 make(chan struct{}),
 		envVars:                options.EnvironmentVariables,
+		enableWireguard:        options.EnableWireguard,
+		postKeys:               options.UploadWireguardKeys,
+		listenWireguardPeers:   options.ListenWireguardPeers,
 	}
 	server.init(ctx)
 	return server
@@ -95,6 +115,11 @@ type agent struct {
 	metadata      atomic.Value
 	startupScript atomic.Bool
 	sshServer     *ssh.Server
+
+	enableWireguard      bool
+	network              *peerwg.Network
+	postKeys             UploadWireguardKeys
+	listenWireguardPeers ListenWireguardPeers
 }

 func (a *agent) run(ctx context.Context) {
@@ -104,6 +129,7 @@ func (a *agent) run(ctx context.Context) {
 	// An exponential back-off occurs when the connection is failing to dial.
 	// This is to prevent server spam in case of a coderd outage.
 	for retrier := retry.New(50*time.Millisecond, 10*time.Second); retrier.Wait(ctx); {
+		a.logger.Info(ctx, "connecting")
 		metadata, peerListener, err = a.dialer(ctx, a.logger)
 		if err != nil {
 			if errors.Is(err, context.Canceled) {
@@ -138,6 +164,13 @@ func (a *agent) run(ctx context.Context) {
 		}()
 	}

+	if a.enableWireguard {
+		err = a.startWireguard(ctx, metadata.WireguardAddresses)
+		if err != nil {
+			a.logger.Error(ctx, "start wireguard", slog.Error(err))
+		}
+	}
+
 	for {
 		conn, err := peerListener.Accept()
 		if err != nil {
@@ -223,6 +256,7 @@ func (a *agent) handlePeerConn(ctx context.Context, conn *peer.Conn) {
 }

 func (a *agent) init(ctx context.Context) {
+	a.logger.Info(ctx, "generating host key")
 	// Clients' should ignore the host key when connecting.
 	// The agent needs to authenticate with coderd to SSH,
 	// so SSH authentication doesn't improve security.
@@ -246,9 +280,17 @@ func (a *agent) init(ctx context.Context) {
 		},
 		Handler: func(session ssh.Session) {
 			err := a.handleSSHSession(session)
+			var exitError *exec.ExitError
+			if xerrors.As(err, &exitError) {
+				a.logger.Debug(ctx, "ssh session returned", slog.Error(exitError))
+				_ = session.Exit(exitError.ExitCode())
+				return
+			}
 			if err != nil {
 				a.logger.Warn(ctx, "ssh session failed", slog.Error(err))
-				_ = session.Exit(1)
+				// This exit code is designed to be unlikely to be confused for a legit exit code
+				// from the process.
+				_ = session.Exit(MagicSessionErrorCode)
 				return
 			}
 		},
@@ -352,37 +394,44 @@ func (a *agent) createCommand(ctx context.Context, rawCommand string, env []stri
 	if err != nil {
 		return nil, xerrors.Errorf("getting os executable: %w", err)
 	}
+	// Set environment variables reliable detection of being inside a
+	// Coder workspace.
+	cmd.Env = append(cmd.Env, "CODER=true")
+
 	cmd.Env = append(cmd.Env, fmt.Sprintf("USER=%s", username))
 	// Git on Windows resolves with UNIX-style paths.
 	// If using backslashes, it's unable to find the executable.
 	unixExecutablePath := strings.ReplaceAll(executablePath, "\\", "/")
 	cmd.Env = append(cmd.Env, fmt.Sprintf(`GIT_SSH_COMMAND=%s gitssh --`, unixExecutablePath))
-	// These prevent the user from having to specify _anything_ to successfully commit.
-	// Both author and committer must be set!
-	cmd.Env = append(cmd.Env, fmt.Sprintf(`GIT_AUTHOR_EMAIL=%s`, metadata.OwnerEmail))
-	cmd.Env = append(cmd.Env, fmt.Sprintf(`GIT_COMMITTER_EMAIL=%s`, metadata.OwnerEmail))
-	cmd.Env = append(cmd.Env, fmt.Sprintf(`GIT_AUTHOR_NAME=%s`, metadata.OwnerUsername))
-	cmd.Env = append(cmd.Env, fmt.Sprintf(`GIT_COMMITTER_NAME=%s`, metadata.OwnerUsername))
+
+	// Set SSH connection environment variables (these are also set by OpenSSH
+	// and thus expected to be present by SSH clients). Since the agent does
+	// networking in-memory, trying to provide accurate values here would be
+	// nonsensical. For now, we hard code these values so that they're present.
+	srcAddr, srcPort := "0.0.0.0", "0"
+	dstAddr, dstPort := "0.0.0.0", "0"
+	cmd.Env = append(cmd.Env, fmt.Sprintf("SSH_CLIENT=%s %s %s", srcAddr, srcPort, dstPort))
+	cmd.Env = append(cmd.Env, fmt.Sprintf("SSH_CONNECTION=%s %s %s %s", srcAddr, srcPort, dstAddr, dstPort))

 	// Load environment variables passed via the agent.
 	// These should override all variables we manually specify.
-	for key, value := range metadata.EnvironmentVariables {
+	for envKey, value := range metadata.EnvironmentVariables {
 		// Expanding environment variables allows for customization
-		// of the $PATH, among other variables. Customers can prepand
+		// of the $PATH, among other variables. Customers can prepend
 		// or append to the $PATH, so allowing expand is required!
-		cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", key, os.ExpandEnv(value)))
+		cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", envKey, os.ExpandEnv(value)))
 	}

 	// Agent-level environment variables should take over all!
 	// This is used for setting agent-specific variables like "CODER_AGENT_TOKEN".
-	for key, value := range a.envVars {
-		cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", key, value))
+	for envKey, value := range a.envVars {
+		cmd.Env = append(cmd.Env, fmt.Sprintf("%s=%s", envKey, value))
 	}

 	return cmd, nil
 }

-func (a *agent) handleSSHSession(session ssh.Session) error {
+func (a *agent) handleSSHSession(session ssh.Session) (retErr error) {
 	cmd, err := a.createCommand(session.Context(), session.RawCommand(), session.Environ())
 	if err != nil {
 		return err
@@ -401,19 +450,31 @@ func (a *agent) handleSSHSession(session ssh.Session) error {
 	sshPty, windowSize, isPty := session.Pty()
 	if isPty {
 		cmd.Env = append(cmd.Env, fmt.Sprintf("TERM=%s", sshPty.Term))
+
+		// The pty package sets `SSH_TTY` on supported platforms.
 		ptty, process, err := pty.Start(cmd)
 		if err != nil {
 			return xerrors.Errorf("start command: %w", err)
 		}
+		defer func() {
+			closeErr := ptty.Close()
+			if closeErr != nil {
+				a.logger.Warn(context.Background(), "failed to close tty",
+					slog.Error(closeErr))
+				if retErr == nil {
+					retErr = closeErr
+				}
+			}
+		}()
 		err = ptty.Resize(uint16(sshPty.Window.Height), uint16(sshPty.Window.Width))
 		if err != nil {
 			return xerrors.Errorf("resize ptty: %w", err)
 		}
 		go func() {
 			for win := range windowSize {
-				err = ptty.Resize(uint16(win.Height), uint16(win.Width))
-				if err != nil {
-					a.logger.Warn(context.Background(), "failed to resize tty", slog.Error(err))
+				resizeErr := ptty.Resize(uint16(win.Height), uint16(win.Width))
+				if resizeErr != nil {
+					a.logger.Warn(context.Background(), "failed to resize tty", slog.Error(resizeErr))
 				}
 			}
 		}()
@@ -423,9 +484,15 @@ func (a *agent) handleSSHSession(session ssh.Session) error {
 		go func() {
 			_, _ = io.Copy(session, ptty.Output())
 		}()
-		_, _ = process.Wait()
-		_ = ptty.Close()
-		return nil
+		err = process.Wait()
+		var exitErr *exec.ExitError
+		// ExitErrors just mean the command we run returned a non-zero exit code, which is normal
+		// and not something to be concerned about.  But, if it's something else, we should log it.
+		if err != nil && !xerrors.As(err, &exitErr) {
+			a.logger.Warn(context.Background(), "wait error",
+				slog.Error(err))
+		}
+		return err
 	}

 	cmd.Stdout = session
@@ -438,6 +505,7 @@ func (a *agent) handleSSHSession(session ssh.Session) error {
 	}
 	go func() {
 		_, _ = io.Copy(stdinPipe, session)
+		_ = stdinPipe.Close()
 	}()
 	err = cmd.Start()
 	if err != nil {
@@ -527,7 +595,7 @@ func (a *agent) handleReconnectingPTY(ctx context.Context, rawID string, conn ne
 		go func() {
 			// If the process dies randomly, we should
 			// close the pty.
-			_, _ = process.Wait()
+			_ = process.Wait()
 			rpty.Close()
 		}()
 		go func() {
@@ -744,7 +812,9 @@ func (r *reconnectingPTY) Close() {
 		_ = conn.Close()
 	}
 	_ = r.ptty.Close()
+	r.circularBufferMutex.Lock()
 	r.circularBuffer.Reset()
+	r.circularBufferMutex.Unlock()
 	r.timeout.Stop()
 }

@@ -16,6 +16,9 @@ import (
 	"testing"
 	"time"

+	"golang.org/x/xerrors"
+
+	scp "github.com/bramvdbogaerde/go-scp"
 	"github.com/google/uuid"
 	"github.com/pion/udp"
 	"github.com/pion/webrtc/v3"
@@ -35,6 +38,7 @@ import (
 	"github.com/coder/coder/peerbroker/proto"
 	"github.com/coder/coder/provisionersdk"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 func TestMain(m *testing.M) {
@@ -68,7 +72,7 @@ func TestAgent(t *testing.T) {
 		require.True(t, strings.HasSuffix(strings.TrimSpace(string(output)), "gitssh --"))
 	})

-	t.Run("SessionTTY", func(t *testing.T) {
+	t.Run("SessionTTYShell", func(t *testing.T) {
 		t.Parallel()
 		if runtime.GOOS == "windows" {
 			// This might be our implementation, or ConPTY itself.
@@ -102,6 +106,29 @@ func TestAgent(t *testing.T) {
 		require.NoError(t, err)
 	})

+	t.Run("SessionTTYExitCode", func(t *testing.T) {
+		t.Parallel()
+		session := setupSSHSession(t, agent.Metadata{})
+		command := "areallynotrealcommand"
+		err := session.RequestPty("xterm", 128, 128, ssh.TerminalModes{})
+		require.NoError(t, err)
+		ptty := ptytest.New(t)
+		require.NoError(t, err)
+		session.Stdout = ptty.Output()
+		session.Stderr = ptty.Output()
+		session.Stdin = ptty.Input()
+		err = session.Start(command)
+		require.NoError(t, err)
+		err = session.Wait()
+		exitErr := &ssh.ExitError{}
+		require.True(t, xerrors.As(err, &exitErr))
+		if runtime.GOOS == "windows" {
+			assert.Equal(t, 1, exitErr.ExitStatus())
+		} else {
+			assert.Equal(t, 127, exitErr.ExitStatus())
+		}
+	})
+
 	t.Run("LocalForwarding", func(t *testing.T) {
 		t.Parallel()
 		random, err := net.Listen("tcp", "127.0.0.1:0")
@@ -119,10 +146,12 @@ func TestAgent(t *testing.T) {
 		localPort := tcpAddr.Port
 		done := make(chan struct{})
 		go func() {
+			defer close(done)
 			conn, err := local.Accept()
-			assert.NoError(t, err)
+			if !assert.NoError(t, err) {
+				return
+			}
 			_ = conn.Close()
-			close(done)
 		}()

 		err = setupSSHCommand(t, []string{"-L", fmt.Sprintf("%d:127.0.0.1:%d", randomPort, localPort)}, []string{"echo", "test"}).Start()
@@ -149,6 +178,20 @@ func TestAgent(t *testing.T) {
 		require.NoError(t, err)
 	})

+	t.Run("SCP", func(t *testing.T) {
+		t.Parallel()
+		sshClient, err := setupAgent(t, agent.Metadata{}, 0).SSHClient()
+		require.NoError(t, err)
+		scpClient, err := scp.NewClientBySSH(sshClient)
+		require.NoError(t, err)
+		tempFile := filepath.Join(t.TempDir(), "scp")
+		content := "hello world"
+		err = scpClient.CopyFile(context.Background(), strings.NewReader(content), tempFile, "0755")
+		require.NoError(t, err)
+		_, err = os.Stat(tempFile)
+		require.NoError(t, err)
+	})
+
 	t.Run("EnvironmentVariables", func(t *testing.T) {
 		t.Parallel()
 		key := "EXAMPLE"
@@ -189,9 +232,52 @@ func TestAgent(t *testing.T) {
 		require.Equal(t, expect, strings.TrimSpace(string(output)))
 	})

+	t.Run("Coder env vars", func(t *testing.T) {
+		t.Parallel()
+
+		for _, key := range []string{"CODER"} {
+			key := key
+			t.Run(key, func(t *testing.T) {
+				t.Parallel()
+
+				session := setupSSHSession(t, agent.Metadata{})
+				command := "sh -c 'echo $" + key + "'"
+				if runtime.GOOS == "windows" {
+					command = "cmd.exe /c echo %" + key + "%"
+				}
+				output, err := session.Output(command)
+				require.NoError(t, err)
+				require.NotEmpty(t, strings.TrimSpace(string(output)))
+			})
+		}
+	})
+
+	t.Run("SSH connection env vars", func(t *testing.T) {
+		t.Parallel()
+
+		// Note: the SSH_TTY environment variable should only be set for TTYs.
+		// For some reason this test produces a TTY locally and a non-TTY in CI
+		// so we don't test for the absence of SSH_TTY.
+		for _, key := range []string{"SSH_CONNECTION", "SSH_CLIENT"} {
+			key := key
+			t.Run(key, func(t *testing.T) {
+				t.Parallel()
+
+				session := setupSSHSession(t, agent.Metadata{})
+				command := "sh -c 'echo $" + key + "'"
+				if runtime.GOOS == "windows" {
+					command = "cmd.exe /c echo %" + key + "%"
+				}
+				output, err := session.Output(command)
+				require.NoError(t, err)
+				require.NotEmpty(t, strings.TrimSpace(string(output)))
+			})
+		}
+	})
+
 	t.Run("StartupScript", func(t *testing.T) {
 		t.Parallel()
-		tempPath := filepath.Join(os.TempDir(), "content.txt")
+		tempPath := filepath.Join(t.TempDir(), "content.txt")
 		content := "somethingnice"
 		setupAgent(t, agent.Metadata{
 			StartupScript: fmt.Sprintf("echo %s > %s", content, tempPath),
@@ -209,11 +295,13 @@ func TestAgent(t *testing.T) {
 			if runtime.GOOS == "windows" {
 				// Windows uses UTF16! 🪟🪟🪟
 				content, _, err = transform.Bytes(unicode.UTF16(unicode.LittleEndian, unicode.UseBOM).NewDecoder(), content)
-				require.NoError(t, err)
+				if !assert.NoError(t, err) {
+					return false
+				}
 			}
 			gotContent = string(content)
 			return true
-		}, 15*time.Second, 100*time.Millisecond)
+		}, testutil.WaitMedium, testutil.IntervalMedium)
 		require.Equal(t, content, strings.TrimSpace(gotContent))
 	})

@@ -309,12 +397,7 @@ func TestAgent(t *testing.T) {
 						t.Skip("Unix socket forwarding isn't supported on Windows")
 					}

-					tmpDir, err := os.MkdirTemp("", "coderd_agent_test_")
-					require.NoError(t, err, "create temp dir for unix listener")
-					t.Cleanup(func() {
-						_ = os.RemoveAll(tmpDir)
-					})
-
+					tmpDir := t.TempDir()
 					l, err := net.Listen("unix", filepath.Join(tmpDir, "test.sock"))
 					require.NoError(t, err, "create UDP listener")
 					return l
@@ -387,15 +470,18 @@ func setupSSHCommand(t *testing.T, beforeArgs []string, afterArgs []string) *exe
 	listener, err := net.Listen("tcp", "127.0.0.1:0")
 	require.NoError(t, err)
 	go func() {
+		defer listener.Close()
 		for {
 			conn, err := listener.Accept()
 			if err != nil {
 				return
 			}
 			ssh, err := agentConn.SSH()
-			assert.NoError(t, err)
-			go io.Copy(conn, ssh)
-			go io.Copy(ssh, conn)
+			if !assert.NoError(t, err) {
+				_ = conn.Close()
+				return
+			}
+			go agent.Bicopy(context.Background(), conn, ssh)
 		}
 	}()
 	t.Cleanup(func() {
@@ -0,0 +1,28 @@
+package reaper
+
+import "github.com/hashicorp/go-reap"
+
+type Option func(o *options)
+
+// WithExecArgs specifies the exec arguments for the fork exec call.
+// By default the same arguments as the parent are used as dictated by
+// os.Args. Since ForkReap calls a fork-exec it is the responsibility of
+// the caller to avoid fork-bombing oneself.
+func WithExecArgs(args ...string) Option {
+	return func(o *options) {
+		o.ExecArgs = args
+	}
+}
+
+// WithPIDCallback sets the channel that reaped child process PIDs are pushed
+// onto.
+func WithPIDCallback(ch reap.PidCh) Option {
+	return func(o *options) {
+		o.PIDs = ch
+	}
+}
+
+type options struct {
+	ExecArgs []string
+	PIDs     reap.PidCh
+}
@@ -2,18 +2,11 @@

 package reaper

-import "github.com/hashicorp/go-reap"
-
-// IsChild returns true if we're the forked process.
-func IsChild() bool {
-	return false
-}
-
 // IsInitProcess returns true if the current process's PID is 1.
 func IsInitProcess() bool {
 	return false
 }

-func ForkReap(_ reap.PidCh) error {
+func ForkReap(_ ...Option) error {
 	return nil
 }
@@ -12,6 +12,7 @@ import (
 	"github.com/stretchr/testify/require"

 	"github.com/coder/coder/agent/reaper"
+	"github.com/coder/coder/testutil"
 )

 func TestReap(t *testing.T) {
@@ -24,17 +25,17 @@ func TestReap(t *testing.T) {
 		t.Skip("Detected CI, skipping reaper tests")
 	}

-	// Because we're forkexecing these tests will try to run twice...
-	if reaper.IsChild() {
-		t.Skip("I'm a child!")
-	}
-
 	// OK checks that's the reaper is successfully reaping
 	// exited processes and passing the PIDs through the shared
 	// channel.
 	t.Run("OK", func(t *testing.T) {
+		t.Parallel()
 		pids := make(reap.PidCh, 1)
-		err := reaper.ForkReap(pids)
+		err := reaper.ForkReap(
+			reaper.WithPIDCallback(pids),
+			// Provide some argument that immediately exits.
+			reaper.WithExecArgs("/bin/sh", "-c", "exit 0"),
+		)
 		require.NoError(t, err)

 		cmd := exec.Command("tail", "-f", "/dev/null")
@@ -53,10 +54,9 @@ func TestReap(t *testing.T) {

 		expectedPIDs := []int{cmd.Process.Pid, cmd2.Process.Pid}

-		deadline := time.NewTimer(time.Second * 5)
 		for i := 0; i < len(expectedPIDs); i++ {
 			select {
-			case <-deadline.C:
+			case <-time.After(testutil.WaitShort):
 				t.Fatalf("Timed out waiting for process")
 			case pid := <-pids:
 				require.Contains(t, expectedPIDs, pid)
@@ -3,7 +3,6 @@
 package reaper

 import (
-	"fmt"
 	"os"
 	"syscall"

@@ -11,17 +10,6 @@ import (
 	"golang.org/x/xerrors"
 )

-// agentEnvMark is a simple environment variable that we use as a marker
-// to indicated that the process is a child as opposed to the reaper.
-// Since we are forkexec'ing we need to be able to differentiate between
-// the two to avoid fork bombing ourselves.
-const agentEnvMark = "CODER_DO_NOT_REAP"
-
-// IsChild returns true if we're the forked process.
-func IsChild() bool {
-	return os.Getenv(agentEnvMark) != ""
-}
-
 // IsInitProcess returns true if the current process's PID is 1.
 func IsInitProcess() bool {
 	return os.Getpid() == 1
@@ -33,19 +21,16 @@ func IsInitProcess() bool {
 // the reaper and an exec.Command waiting for its process to complete.
 // The provided 'pids' channel may be nil if the caller does not care about the
 // reaped children PIDs.
-func ForkReap(pids reap.PidCh) error {
-	// Check if the process is the parent or the child.
-	// If it's the child we want to skip attempting to reap.
-	if IsChild() {
-		return nil
+func ForkReap(opt ...Option) error {
+	opts := &options{
+		ExecArgs: os.Args,
 	}

-	go reap.ReapChildren(pids, nil, nil, nil)
+	for _, o := range opt {
+		o(opts)
+	}

-	args := os.Args
-	// This is simply done to help identify the real agent process
-	// when viewing in something like 'ps'.
-	args = append(args, "#Agent")
+	go reap.ReapChildren(opts.PIDs, nil, nil, nil)

 	pwd, err := os.Getwd()
 	if err != nil {
@@ -54,8 +39,7 @@ func ForkReap(pids reap.PidCh) error {

 	pattrs := &syscall.ProcAttr{
 		Dir: pwd,
-		// Add our marker for identifying the child process.
-		Env: append(os.Environ(), fmt.Sprintf("%s=true", agentEnvMark)),
+		Env: os.Environ(),
 		Sys: &syscall.SysProcAttr{
 			Setsid: true,
 		},
@@ -67,7 +51,7 @@ func ForkReap(pids reap.PidCh) error {
 	}

 	//#nosec G204
-	pid, _ := syscall.ForkExec(args[0], args, pattrs)
+	pid, _ := syscall.ForkExec(opts.ExecArgs[0], opts.ExecArgs, pattrs)

 	var wstatus syscall.WaitStatus
 	_, err = syscall.Wait4(pid, &wstatus, 0, nil)
@@ -0,0 +1,97 @@
+package agent
+
+import (
+	"context"
+	"net"
+	"strconv"
+
+	"golang.org/x/xerrors"
+	"inet.af/netaddr"
+
+	"cdr.dev/slog"
+	"github.com/coder/coder/peer/peerwg"
+)
+
+func (a *agent) startWireguard(ctx context.Context, addrs []netaddr.IPPrefix) error {
+	if a.network != nil {
+		_ = a.network.Close()
+		a.network = nil
+	}
+
+	// We can't create a wireguard network without these.
+	if len(addrs) == 0 || a.listenWireguardPeers == nil || a.postKeys == nil {
+		return xerrors.New("wireguard is enabled, but no addresses were provided or necessary functions were not provided")
+	}
+
+	wg, err := peerwg.New(a.logger.Named("wireguard"), addrs)
+	if err != nil {
+		return xerrors.Errorf("create wireguard network: %w", err)
+	}
+
+	// A new keypair is generated on each agent start.
+	// This keypair must be sent to Coder to allow for incoming connections.
+	err = a.postKeys(ctx, WireguardPublicKeys{
+		Public: wg.NodePrivateKey.Public(),
+		Disco:  wg.DiscoPublicKey,
+	})
+	if err != nil {
+		a.logger.Warn(ctx, "post keys", slog.Error(err))
+	}
+
+	go func() {
+		for {
+			ch, listenClose, err := a.listenWireguardPeers(ctx, a.logger)
+			if err != nil {
+				a.logger.Warn(ctx, "listen wireguard peers", slog.Error(err))
+				return
+			}
+
+			for {
+				peer, ok := <-ch
+				if !ok {
+					break
+				}
+
+				err := wg.AddPeer(peer)
+				a.logger.Info(ctx, "added wireguard peer", slog.F("peer", peer.NodePublicKey.ShortString()), slog.Error(err))
+			}
+
+			listenClose()
+		}
+	}()
+
+	a.startWireguardListeners(ctx, wg, []handlerPort{
+		{port: 12212, handler: a.sshServer.HandleConn},
+	})
+
+	a.network = wg
+	return nil
+}
+
+type handlerPort struct {
+	handler func(conn net.Conn)
+	port    uint16
+}
+
+func (a *agent) startWireguardListeners(ctx context.Context, network *peerwg.Network, handlers []handlerPort) {
+	for _, h := range handlers {
+		go func(h handlerPort) {
+			a.logger.Debug(ctx, "starting wireguard listener", slog.F("port", h.port))
+
+			listener, err := network.Listen("tcp", net.JoinHostPort("", strconv.Itoa(int(h.port))))
+			if err != nil {
+				a.logger.Warn(ctx, "listen wireguard", slog.F("port", h.port), slog.Error(err))
+				return
+			}
+
+			for {
+				conn, err := listener.Accept()
+				if err != nil {
+					return
+				}
+
+				go h.handler(conn)
+			}
+		}(h)
+	}
+}
@@ -3,6 +3,7 @@ package buildinfo
 import (
 	"fmt"
 	"runtime/debug"
+	"strings"
 	"sync"
 	"time"

@@ -24,6 +25,11 @@ var (
 	tag string
 )

+const (
+	// develPrefix is prefixed to developer versions of the application.
+	develPrefix = "v0.0.0-devel"
+)
+
 // Version returns the semantic version of the build.
 // Use golang.org/x/mod/semver to compare versions.
 func Version() string {
@@ -35,7 +41,7 @@ func Version() string {
 		if tag == "" {
 			// This occurs when the tag hasn't been injected,
 			// like when using "go run".
-			version = "v0.0.0-devel" + revision
+			version = develPrefix + revision
 			return
 		}
 		version = "v" + tag
@@ -48,6 +54,20 @@ func Version() string {
 	return version
 }

+// VersionsMatch compares the two versions. It assumes the versions match if
+// the major and the minor versions are equivalent. Patch versions are
+// disregarded. If it detects that either version is a developer build it
+// returns true.
+func VersionsMatch(v1, v2 string) bool {
+	// Developer versions are disregarded...hopefully they know what they are
+	// doing.
+	if strings.HasPrefix(v1, develPrefix) || strings.HasPrefix(v2, develPrefix) {
+		return true
+	}
+
+	return semver.MajorMinor(v1) == semver.MajorMinor(v2)
+}
+
 // ExternalURL returns a URL referencing the current Coder version.
 // For production builds, this will link directly to a release.
 // For development builds, this will link to a commit.
@@ -1,6 +1,7 @@
 package buildinfo_test

 import (
+	"fmt"
 	"testing"

 	"github.com/stretchr/testify/require"
@@ -29,4 +30,70 @@ func TestBuildInfo(t *testing.T) {
 		_, valid := buildinfo.Time()
 		require.False(t, valid)
 	})
+
+	t.Run("VersionsMatch", func(t *testing.T) {
+		t.Parallel()
+
+		type testcase struct {
+			name        string
+			v1          string
+			v2          string
+			expectMatch bool
+		}
+
+		cases := []testcase{
+			{
+				name:        "OK",
+				v1:          "v1.2.3",
+				v2:          "v1.2.3",
+				expectMatch: true,
+			},
+			// Test that we return true if a developer version is detected.
+			// Developers do not need to be warned of mismatched versions.
+			{
+				name:        "DevelIgnored",
+				v1:          "v0.0.0-devel+123abac",
+				v2:          "v1.2.3",
+				expectMatch: true,
+			},
+			// Our CI instance uses a "-devel" prerelease
+			// flag. This is not the same as a developer WIP build.
+			{
+				name:        "DevelPreleaseNotIgnored",
+				v1:          "v1.1.1-devel+123abac",
+				v2:          "v1.2.3",
+				expectMatch: false,
+			},
+			{
+				name:        "MajorMismatch",
+				v1:          "v1.2.3",
+				v2:          "v0.1.2",
+				expectMatch: false,
+			},
+			{
+				name:        "MinorMismatch",
+				v1:          "v1.2.3",
+				v2:          "v1.3.2",
+				expectMatch: false,
+			},
+			// Different patches are ok, breaking changes are not allowed
+			// in patches.
+			{
+				name:        "PatchMismatch",
+				v1:          "v1.2.3+hash.whocares",
+				v2:          "v1.2.4+somestuff.hm.ok",
+				expectMatch: true,
+			},
+		}
+
+		for _, c := range cases {
+			c := c
+			t.Run(c.name, func(t *testing.T) {
+				t.Parallel()
+				require.Equal(t, c.expectMatch, buildinfo.VersionsMatch(c.v1, c.v2),
+					fmt.Sprintf("expected match=%v for version %s and %s", c.expectMatch, c.v1, c.v2),
+				)
+			})
+		}
+	})
 }
@@ -14,17 +14,15 @@ import (
 	"cloud.google.com/go/compute/metadata"
 	"github.com/spf13/cobra"
 	"golang.org/x/xerrors"
+	"gopkg.in/natefinch/lumberjack.v2"

 	"cdr.dev/slog"
 	"cdr.dev/slog/sloggers/sloghuman"
-
 	"github.com/coder/coder/agent"
 	"github.com/coder/coder/agent/reaper"
 	"github.com/coder/coder/cli/cliflag"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/retry"
-
-	"gopkg.in/natefinch/lumberjack.v2"
 )

 func workspaceAgent() *cobra.Command {
@@ -32,6 +30,8 @@ func workspaceAgent() *cobra.Command {
 		auth         string
 		pprofEnabled bool
 		pprofAddress string
+		noReap       bool
+		wireguard    bool
 	)
 	cmd := &cobra.Command{
 		Use: "agent",
@@ -58,9 +58,12 @@ func workspaceAgent() *cobra.Command {

 			// Spawn a reaper so that we don't accumulate a ton
 			// of zombie processes.
-			if reaper.IsInitProcess() && !reaper.IsChild() && isLinux {
+			if reaper.IsInitProcess() && !noReap && isLinux {
 				logger.Info(cmd.Context(), "spawning reaper process")
-				err := reaper.ForkReap(nil)
+				// Do not start a reaper on the child process. It's important
+				// to do this else we fork bomb ourselves.
+				args := append(os.Args, "--no-reap")
+				err := reaper.ForkReap(reaper.WithExecArgs(args...))
 				if err != nil {
 					logger.Error(cmd.Context(), "failed to reap", slog.Error(err))
 					return xerrors.Errorf("fork reap: %w", err)
@@ -70,6 +73,7 @@ func workspaceAgent() *cobra.Command {
 				return nil
 			}

+			logger.Info(cmd.Context(), "starting agent", slog.F("url", coderURL), slog.F("auth", auth))
 			client := codersdk.New(coderURL)

 			if pprofEnabled {
@@ -135,6 +139,7 @@ func workspaceAgent() *cobra.Command {
 			}

 			if exchangeToken != nil {
+				logger.Info(cmd.Context(), "exchanging identity token")
 				// Agent's can start before resources are returned from the provisioner
 				// daemon. If there are many resources being provisioned, this time
 				// could be significant. This is arbitrarily set at an hour to prevent
@@ -174,6 +179,9 @@ func workspaceAgent() *cobra.Command {
 					// shells so "gitssh" works!
 					"CODER_AGENT_TOKEN": client.SessionToken,
 				},
+				EnableWireguard:      wireguard,
+				UploadWireguardKeys:  client.UploadWorkspaceAgentKeys,
+				ListenWireguardPeers: client.WireguardPeerListener,
 			})
 			<-cmd.Context().Done()
 			return closer.Close()
@@ -182,6 +190,8 @@ func workspaceAgent() *cobra.Command {

 	cliflag.StringVarP(cmd.Flags(), &auth, "auth", "", "CODER_AGENT_AUTH", "token", "Specify the authentication type to use for the agent")
 	cliflag.BoolVarP(cmd.Flags(), &pprofEnabled, "pprof-enable", "", "CODER_AGENT_PPROF_ENABLE", false, "Enable serving pprof metrics on the address defined by --pprof-address.")
+	cliflag.BoolVarP(cmd.Flags(), &noReap, "no-reap", "", "", false, "Do not start a process reaper.")
 	cliflag.StringVarP(cmd.Flags(), &pprofAddress, "pprof-address", "", "CODER_AGENT_PPROF_ADDRESS", "127.0.0.1:6060", "The address to serve pprof.")
+	cliflag.BoolVarP(cmd.Flags(), &wireguard, "wireguard", "", "CODER_AGENT_WIREGUARD", true, "Whether to start the Wireguard interface.")
 	return cmd
 }
@@ -46,7 +46,7 @@ func TestWorkspaceAgent(t *testing.T) {
 		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
 		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

-		cmd, _ := clitest.New(t, "agent", "--auth", "azure-instance-identity", "--agent-url", client.URL.String())
+		cmd, _ := clitest.New(t, "agent", "--auth", "azure-instance-identity", "--agent-url", client.URL.String(), "--wireguard=false")
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
 		errC := make(chan error)
@@ -101,7 +101,7 @@ func TestWorkspaceAgent(t *testing.T) {
 		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
 		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

-		cmd, _ := clitest.New(t, "agent", "--auth", "aws-instance-identity", "--agent-url", client.URL.String())
+		cmd, _ := clitest.New(t, "agent", "--auth", "aws-instance-identity", "--agent-url", client.URL.String(), "--wireguard=false")
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
 		errC := make(chan error)
@@ -156,7 +156,7 @@ func TestWorkspaceAgent(t *testing.T) {
 		workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
 		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

-		cmd, _ := clitest.New(t, "agent", "--auth", "google-instance-identity", "--agent-url", client.URL.String())
+		cmd, _ := clitest.New(t, "agent", "--auth", "google-instance-identity", "--agent-url", client.URL.String(), "--wireguard=false")
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
 		errC := make(chan error)
@@ -6,8 +6,7 @@
 //
 // Will produce the following usage docs:
 //
-//   -a, --address string              The address to serve the API and dashboard (uses $CODER_ADDRESS). (default "127.0.0.1:3000")
-//
+//	-a, --address string              The address to serve the API and dashboard (uses $CODER_ADDRESS). (default "127.0.0.1:3000")
 package cliflag

 import (
@@ -17,9 +16,33 @@ import (
 	"strings"
 	"time"

+	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
 )

+// IsSetBool returns the value of the boolean flag if it is set.
+// It returns false if the flag isn't set or if any error occurs attempting
+// to parse the value of the flag.
+func IsSetBool(cmd *cobra.Command, name string) bool {
+	val, ok := IsSet(cmd, name)
+	if !ok {
+		return false
+	}
+
+	b, err := strconv.ParseBool(val)
+	return err == nil && b
+}
+
+// IsSet returns the string value of the flag and whether it was set.
+func IsSet(cmd *cobra.Command, name string) (string, bool) {
+	flag := cmd.Flag(name)
+	if flag == nil {
+		return "", false
+	}
+
+	return flag.Value.String(), flag.Changed
+}
+
 // String sets a string flag on the given flag set.
 func String(flagset *pflag.FlagSet, name, shorthand, env, def, usage string) {
 	v, ok := os.LookupEnv(env)
@@ -47,7 +70,7 @@ func StringArrayVarP(flagset *pflag.FlagSet, ptr *[]string, name string, shortha
 			def = strings.Split(val, ",")
 		}
 	}
-	flagset.StringArrayVarP(ptr, name, shorthand, def, usage)
+	flagset.StringArrayVarP(ptr, name, shorthand, def, fmtUsage(usage, env))
 }

 // Uint8VarP sets a uint8 flag on the given flag set.
@@ -67,6 +90,22 @@ func Uint8VarP(flagset *pflag.FlagSet, ptr *uint8, name string, shorthand string
 	flagset.Uint8VarP(ptr, name, shorthand, uint8(vi64), fmtUsage(usage, env))
 }

+func Bool(flagset *pflag.FlagSet, name, shorthand, env string, def bool, usage string) {
+	val, ok := os.LookupEnv(env)
+	if !ok || val == "" {
+		flagset.BoolP(name, shorthand, def, fmtUsage(usage, env))
+		return
+	}
+
+	valb, err := strconv.ParseBool(val)
+	if err != nil {
+		flagset.BoolP(name, shorthand, def, fmtUsage(usage, env))
+		return
+	}
+
+	flagset.BoolP(name, shorthand, valb, fmtUsage(usage, env))
+}
+
 // BoolVarP sets a bool flag on the given flag set.
 func BoolVarP(flagset *pflag.FlagSet, ptr *bool, name string, shorthand string, env string, def bool, usage string) {
 	val, ok := os.LookupEnv(env)
@@ -102,9 +141,14 @@ func DurationVarP(flagset *pflag.FlagSet, ptr *time.Duration, name string, short
 }

 func fmtUsage(u string, env string) string {
-	if env == "" {
-		return fmt.Sprintf("%s.", u)
+	if env != "" {
+		// Avoid double dotting.
+		dot := "."
+		if strings.HasSuffix(u, ".") {
+			dot = ""
+		}
+		u = fmt.Sprintf("%s%s\nConsumes $%s", u, dot, env)
 	}

-	return fmt.Sprintf("%s - consumes $%s.", u, env)
+	return u
 }
@@ -14,6 +14,7 @@ import (
 )

 // Testcliflag cannot run in parallel because it uses t.Setenv.
+//
 //nolint:paralleltest
 func TestCliflag(t *testing.T) {
 	t.Run("StringDefault", func(t *testing.T) {
@@ -24,7 +25,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, def, got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf(" - consumes $%s", env))
+		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf("Consumes $%s", env))
 	})

 	t.Run("StringEnvVar", func(t *testing.T) {
@@ -48,7 +49,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, def, got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf(" - consumes $%s", env))
+		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf("Consumes $%s", env))
 	})

 	t.Run("StringVarPEnvVar", func(t *testing.T) {
@@ -74,7 +75,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, def, got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.NotContains(t, flagset.FlagUsages(), " - consumes")
+		require.NotContains(t, flagset.FlagUsages(), "Consumes")
 	})

 	t.Run("StringArrayDefault", func(t *testing.T) {
@@ -117,7 +118,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, uint8(def), got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf(" - consumes $%s", env))
+		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf("Consumes $%s", env))
 	})

 	t.Run("IntEnvVar", func(t *testing.T) {
@@ -156,7 +157,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, def, got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf(" - consumes $%s", env))
+		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf("Consumes $%s", env))
 	})

 	t.Run("BoolEnvVar", func(t *testing.T) {
@@ -195,7 +196,7 @@ func TestCliflag(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, def, got)
 		require.Contains(t, flagset.FlagUsages(), usage)
-		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf(" - consumes $%s", env))
+		require.Contains(t, flagset.FlagUsages(), fmt.Sprintf("Consumes $%s", env))
 	})

 	t.Run("DurationEnvVar", func(t *testing.T) {
@@ -21,10 +21,22 @@ import (
 // New creates a CLI instance with a configuration pointed to a
 // temporary testing directory.
 func New(t *testing.T, args ...string) (*cobra.Command, config.Root) {
-	cmd := cli.Root()
+	return NewWithSubcommands(t, cli.AGPL(), args...)
+}
+
+func NewWithSubcommands(
+	t *testing.T, subcommands []*cobra.Command, args ...string,
+) (*cobra.Command, config.Root) {
+	cmd := cli.Root(subcommands)
 	dir := t.TempDir()
 	root := config.Root(dir)
 	cmd.SetArgs(append([]string{"--global-config", dir}, args...))
+
+	// We could consider using writers
+	// that log via t.Log here instead.
+	cmd.SetOut(io.Discard)
+	cmd.SetErr(io.Discard)
+
 	return cmd, root
 }

@@ -79,7 +79,7 @@ func Agent(ctx context.Context, writer io.Writer, opts AgentOptions) error {
 		defer resourceMutex.Unlock()
 		message := "Don't panic, your workspace is booting up!"
 		if agent.Status == codersdk.WorkspaceAgentDisconnected {
-			message = "The workspace agent lost connection! Wait for it to reconnect or run: " + Styles.Code.Render("coder rebuild "+opts.WorkspaceName)
+			message = "The workspace agent lost connection! Wait for it to reconnect or restart your workspace."
 		}
 		// This saves the cursor position, then defers clearing from the cursor
 		// position to the end of the screen.
@@ -26,6 +26,7 @@ var Styles = struct {
 	Checkmark,
 	Code,
 	Crossmark,
+	DateTimeStamp,
 	Error,
 	Field,
 	Keyword,
@@ -33,7 +34,7 @@ var Styles = struct {
 	Placeholder,
 	Prompt,
 	FocusedPrompt,
-	Fuschia,
+	Fuchsia,
 	Logo,
 	Warn,
 	Wrap lipgloss.Style
@@ -42,15 +43,16 @@ var Styles = struct {
 	Checkmark:     defaultStyles.Checkmark,
 	Code:          defaultStyles.Code,
 	Crossmark:     defaultStyles.Error.Copy().SetString("✘"),
+	DateTimeStamp: defaultStyles.LabelDim,
 	Error:         defaultStyles.Error,
 	Field:         defaultStyles.Code.Copy().Foreground(lipgloss.AdaptiveColor{Light: "#000000", Dark: "#FFFFFF"}),
 	Keyword:       defaultStyles.Keyword,
 	Paragraph:     defaultStyles.Paragraph,
-	Placeholder:   lipgloss.NewStyle().Foreground(lipgloss.Color("240")),
+	Placeholder:   lipgloss.NewStyle().Foreground(lipgloss.AdaptiveColor{Light: "#585858", Dark: "#005fff"}),
 	Prompt:        defaultStyles.Prompt.Foreground(lipgloss.AdaptiveColor{Light: "#9B9B9B", Dark: "#5C5C5C"}),
 	FocusedPrompt: defaultStyles.FocusedPrompt.Foreground(lipgloss.Color("#651fff")),
-	Fuschia:       defaultStyles.SelectedMenuItem.Copy(),
+	Fuchsia:       defaultStyles.SelectedMenuItem.Copy(),
 	Logo:          defaultStyles.Logo.SetString("Coder"),
 	Warn:          lipgloss.NewStyle().Foreground(lipgloss.AdaptiveColor{Light: "#04B575", Dark: "#ECFD65"}),
-	Wrap:          defaultStyles.Wrap,
+	Wrap:          lipgloss.NewStyle().Width(80),
 }
@@ -47,6 +47,7 @@ func ParameterSchema(cmd *cobra.Command, parameterSchema codersdk.ParameterSchem
 		value, err = Prompt(cmd, PromptOptions{
 			Text: Styles.Bold.Render(text),
 		})
+		value = strings.TrimSpace(value)
 	}
 	if err != nil {
 		return "", err
@@ -24,25 +24,41 @@ type PromptOptions struct {
 	Validate  func(string) error
 }

+const skipPromptFlag = "yes"
+
 func AllowSkipPrompt(cmd *cobra.Command) {
-	cmd.Flags().BoolP("yes", "y", false, "Bypass prompts")
+	cmd.Flags().BoolP(skipPromptFlag, "y", false, "Bypass prompts")
 }

+const (
+	ConfirmYes = "yes"
+	ConfirmNo  = "no"
+)
+
 // Prompt asks the user for input.
 func Prompt(cmd *cobra.Command, opts PromptOptions) (string, error) {
 	// If the cmd has a "yes" flag for skipping confirm prompts, honor it.
 	// If it's not a "Confirm" prompt, then don't skip. As the default value of
 	// "yes" makes no sense.
-	if opts.IsConfirm && cmd.Flags().Lookup("yes") != nil {
-		if skip, _ := cmd.Flags().GetBool("yes"); skip {
-			return "yes", nil
+	if opts.IsConfirm && cmd.Flags().Lookup(skipPromptFlag) != nil {
+		if skip, _ := cmd.Flags().GetBool(skipPromptFlag); skip {
+			return ConfirmYes, nil
 		}
 	}

 	_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.FocusedPrompt.String()+opts.Text+" ")
 	if opts.IsConfirm {
-		opts.Default = "yes"
-		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+Styles.Bold.Render("yes")+Styles.Placeholder.Render("/no) ")))
+		if len(opts.Default) == 0 {
+			opts.Default = ConfirmYes
+		}
+		renderedYes := Styles.Placeholder.Render(ConfirmYes)
+		renderedNo := Styles.Placeholder.Render(ConfirmNo)
+		if opts.Default == ConfirmYes {
+			renderedYes = Styles.Bold.Render(ConfirmYes)
+		} else {
+			renderedNo = Styles.Bold.Render(ConfirmNo)
+		}
+		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+renderedYes+Styles.Placeholder.Render("/"+renderedNo+Styles.Placeholder.Render(") "))))
 	} else if opts.Default != "" {
 		_, _ = fmt.Fprint(cmd.OutOrStdout(), Styles.Placeholder.Render("("+opts.Default+") "))
 	}
@@ -7,7 +7,6 @@ import (
 	"os"
 	"os/exec"
 	"testing"
-	"time"

 	"github.com/spf13/cobra"
 	"github.com/stretchr/testify/assert"
@@ -16,6 +15,7 @@ import (
 	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/pty"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 func TestPrompt(t *testing.T) {
@@ -61,7 +61,7 @@ func TestPrompt(t *testing.T) {
 		// Copy all data written out to a buffer. When we close the ptty, we can
 		// no longer read from the ptty.Output(), but we can read what was
 		// written to the buffer.
-		dataRead, doneReading := context.WithTimeout(context.Background(), time.Second*2)
+		dataRead, doneReading := context.WithTimeout(context.Background(), testutil.WaitShort)
 		go func() {
 			// This will throw an error sometimes. The underlying ptty
 			// has its own cleanup routines in t.Cleanup. Instead of
@@ -165,9 +165,6 @@ func newPrompt(ptty *ptytest.PTY, opts cliui.PromptOptions, cmdOpt func(cmd *cob
 }

 func TestPasswordTerminalState(t *testing.T) {
-	// TODO: fix this test so that it runs reliably
-	t.Skip()
-
 	if os.Getenv("TEST_SUBPROCESS") == "1" {
 		passwordHelper()
 		return
@@ -185,27 +182,28 @@ func TestPasswordTerminalState(t *testing.T) {
 	// connect the child process's stdio to the PTY directly, not via a pipe
 	cmd.Stdin = ptty.Input().Reader
 	cmd.Stdout = ptty.Output().Writer
-	cmd.Stderr = os.Stderr
+	cmd.Stderr = ptty.Output().Writer
 	err := cmd.Start()
 	require.NoError(t, err)
 	process := cmd.Process
 	defer process.Kill()

 	ptty.ExpectMatch("Password: ")
-	time.Sleep(100 * time.Millisecond) // wait for child process to turn off echo and start reading input

-	echo, err := ptyWithFlags.EchoEnabled()
-	require.NoError(t, err)
-	require.False(t, echo, "echo is on while reading password")
+	require.Eventually(t, func() bool {
+		echo, err := ptyWithFlags.EchoEnabled()
+		return err == nil && !echo
+	}, testutil.WaitShort, testutil.IntervalMedium, "echo is on while reading password")

 	err = process.Signal(os.Interrupt)
 	require.NoError(t, err)
 	_, err = process.Wait()
 	require.NoError(t, err)

-	echo, err = ptyWithFlags.EchoEnabled()
-	require.NoError(t, err)
-	require.True(t, echo, "echo is off after reading password")
+	require.Eventually(t, func() bool {
+		echo, err := ptyWithFlags.EchoEnabled()
+		return err == nil && echo
+	}, testutil.WaitShort, testutil.IntervalMedium, "echo is off after reading password")
 }

 // nolint:unused
@@ -1,9 +1,14 @@
 package cliui

 import (
+	"fmt"
+	"reflect"
 	"strings"
+	"time"

+	"github.com/fatih/structtag"
 	"github.com/jedib0t/go-pretty/v6/table"
+	"golang.org/x/xerrors"
 )

 // Table creates a new table with standardized styles.
@@ -41,3 +46,262 @@ func FilterTableColumns(header table.Row, columns []string) []table.ColumnConfig
 	}
 	return columnConfigs
 }
+
+// DisplayTable renders a table as a string. The input argument must be a slice
+// of structs. At least one field in the struct must have a `table:""` tag
+// containing the name of the column in the outputted table.
+//
+// Nested structs are processed if the field has the `table:"$NAME,recursive"`
+// tag and their fields will be named as `$PARENT_NAME $NAME`. If the tag is
+// malformed or a field is marked as recursive but does not contain a struct or
+// a pointer to a struct, this function will return an error (even with an empty
+// input slice).
+//
+// If sort is empty, the input order will be used. If filterColumns is empty or
+// nil, all available columns are included.
+func DisplayTable(out any, sort string, filterColumns []string) (string, error) {
+	v := reflect.Indirect(reflect.ValueOf(out))
+
+	if v.Kind() != reflect.Slice {
+		return "", xerrors.Errorf("DisplayTable called with a non-slice type")
+	}
+
+	// Get the list of table column headers.
+	headersRaw, err := typeToTableHeaders(v.Type().Elem())
+	if err != nil {
+		return "", xerrors.Errorf("get table headers recursively for type %q: %w", v.Type().Elem().String(), err)
+	}
+	if len(headersRaw) == 0 {
+		return "", xerrors.New(`no table headers found on the input type, make sure there is at least one "table" struct tag`)
+	}
+	headers := make(table.Row, len(headersRaw))
+	for i, header := range headersRaw {
+		headers[i] = header
+	}
+
+	// Verify that the given sort column and filter columns are valid.
+	if sort != "" || len(filterColumns) != 0 {
+		headersMap := make(map[string]string, len(headersRaw))
+		for _, header := range headersRaw {
+			headersMap[strings.ToLower(header)] = header
+		}
+
+		if sort != "" {
+			sort = strings.ToLower(strings.ReplaceAll(sort, "_", " "))
+			h, ok := headersMap[sort]
+			if !ok {
+				return "", xerrors.Errorf(`specified sort column %q not found in table headers, available columns are "%v"`, sort, strings.Join(headersRaw, `", "`))
+			}
+
+			// Autocorrect
+			sort = h
+		}
+
+		for i, column := range filterColumns {
+			column := strings.ToLower(strings.ReplaceAll(column, "_", " "))
+			h, ok := headersMap[column]
+			if !ok {
+				return "", xerrors.Errorf(`specified filter column %q not found in table headers, available columns are "%v"`, sort, strings.Join(headersRaw, `", "`))
+			}
+
+			// Autocorrect
+			filterColumns[i] = h
+		}
+	}
+
+	// Verify that the given sort column is valid.
+	if sort != "" {
+		sort = strings.ReplaceAll(sort, "_", " ")
+		found := false
+		for _, header := range headersRaw {
+			if strings.EqualFold(sort, header) {
+				found = true
+				sort = header
+				break
+			}
+		}
+		if !found {
+			return "", xerrors.Errorf("specified sort column %q not found in table headers, available columns are %q", sort, strings.Join(headersRaw, `", "`))
+		}
+	}
+
+	// Setup the table formatter.
+	tw := Table()
+	tw.AppendHeader(headers)
+	tw.SetColumnConfigs(FilterTableColumns(headers, filterColumns))
+	if sort != "" {
+		tw.SortBy([]table.SortBy{{
+			Name: sort,
+		}})
+	}
+
+	// Write each struct to the table.
+	for i := 0; i < v.Len(); i++ {
+		// Format the row as a slice.
+		rowMap, err := valueToTableMap(v.Index(i))
+		if err != nil {
+			return "", xerrors.Errorf("get table row map %v: %w", i, err)
+		}
+
+		rowSlice := make([]any, len(headers))
+		for i, h := range headersRaw {
+			v, ok := rowMap[h]
+			if !ok {
+				v = nil
+			}
+
+			// Special type formatting.
+			switch val := v.(type) {
+			case time.Time:
+				v = val.Format(time.Stamp)
+			case *time.Time:
+				if val != nil {
+					v = val.Format(time.Stamp)
+				}
+			case fmt.Stringer:
+				if val != nil {
+					v = val.String()
+				}
+			}
+
+			rowSlice[i] = v
+		}
+
+		tw.AppendRow(table.Row(rowSlice))
+	}
+
+	return tw.Render(), nil
+}
+
+// parseTableStructTag returns the name of the field according to the `table`
+// struct tag. If the table tag does not exist or is "-", an empty string is
+// returned. If the table tag is malformed, an error is returned.
+//
+// The returned name is transformed from "snake_case" to "normal text".
+func parseTableStructTag(field reflect.StructField) (name string, recurse bool, err error) {
+	tags, err := structtag.Parse(string(field.Tag))
+	if err != nil {
+		return "", false, xerrors.Errorf("parse struct field tag %q: %w", string(field.Tag), err)
+	}
+
+	tag, err := tags.Get("table")
+	if err != nil || tag.Name == "-" {
+		// tags.Get only returns an error if the tag is not found.
+		return "", false, nil
+	}
+
+	recursive := false
+	for _, opt := range tag.Options {
+		if opt == "recursive" {
+			recursive = true
+			continue
+		}
+
+		return "", false, xerrors.Errorf("unknown option %q in struct field tag", opt)
+	}
+
+	return strings.ReplaceAll(tag.Name, "_", " "), recursive, nil
+}
+
+func isStructOrStructPointer(t reflect.Type) bool {
+	return t.Kind() == reflect.Struct || (t.Kind() == reflect.Pointer && t.Elem().Kind() == reflect.Struct)
+}
+
+// typeToTableHeaders converts a type to a slice of column names. If the given
+// type is invalid (not a struct or a pointer to a struct, has invalid table
+// tags, etc.), an error is returned.
+func typeToTableHeaders(t reflect.Type) ([]string, error) {
+	if !isStructOrStructPointer(t) {
+		return nil, xerrors.Errorf("typeToTableHeaders called with a non-struct or a non-pointer-to-a-struct type")
+	}
+	if t.Kind() == reflect.Pointer {
+		t = t.Elem()
+	}
+
+	headers := []string{}
+	for i := 0; i < t.NumField(); i++ {
+		field := t.Field(i)
+		name, recursive, err := parseTableStructTag(field)
+		if err != nil {
+			return nil, xerrors.Errorf("parse struct tags for field %q in type %q: %w", field.Name, t.String(), err)
+		}
+		if name == "" {
+			continue
+		}
+
+		fieldType := field.Type
+		if recursive {
+			if !isStructOrStructPointer(fieldType) {
+				return nil, xerrors.Errorf("field %q in type %q is marked as recursive but does not contain a struct or a pointer to a struct", field.Name, t.String())
+			}
+
+			childNames, err := typeToTableHeaders(fieldType)
+			if err != nil {
+				return nil, xerrors.Errorf("get child field header names for field %q in type %q: %w", field.Name, fieldType.String(), err)
+			}
+			for _, childName := range childNames {
+				headers = append(headers, fmt.Sprintf("%s %s", name, childName))
+			}
+			continue
+		}
+
+		headers = append(headers, name)
+	}
+
+	return headers, nil
+}
+
+// valueToTableMap converts a struct to a map of column name to value. If the
+// given type is invalid (not a struct or a pointer to a struct, has invalid
+// table tags, etc.), an error is returned.
+func valueToTableMap(val reflect.Value) (map[string]any, error) {
+	if !isStructOrStructPointer(val.Type()) {
+		return nil, xerrors.Errorf("valueToTableMap called with a non-struct or a non-pointer-to-a-struct type")
+	}
+	if val.Kind() == reflect.Pointer {
+		if val.IsNil() {
+			// No data for this struct, so return an empty map. All values will
+			// be rendered as nil in the resulting table.
+			return map[string]any{}, nil
+		}
+
+		val = val.Elem()
+	}
+
+	row := map[string]any{}
+	for i := 0; i < val.NumField(); i++ {
+		field := val.Type().Field(i)
+		fieldVal := val.Field(i)
+		name, recursive, err := parseTableStructTag(field)
+		if err != nil {
+			return nil, xerrors.Errorf("parse struct tags for field %q in type %T: %w", field.Name, val, err)
+		}
+		if name == "" {
+			continue
+		}
+
+		// Recurse if it's a struct.
+		fieldType := field.Type
+		if recursive {
+			if !isStructOrStructPointer(fieldType) {
+				return nil, xerrors.Errorf("field %q in type %q is marked as recursive but does not contain a struct or a pointer to a struct", field.Name, fieldType.String())
+			}
+
+			// valueToTableMap does nothing on pointers so we don't need to
+			// filter here.
+			childMap, err := valueToTableMap(fieldVal)
+			if err != nil {
+				return nil, xerrors.Errorf("get child field values for field %q in type %q: %w", field.Name, fieldType.String(), err)
+			}
+			for childName, childValue := range childMap {
+				row[fmt.Sprintf("%s %s", name, childName)] = childValue
+			}
+			continue
+		}
+
+		// Otherwise, we just use the field value.
+		row[name] = val.Field(i).Interface()
+	}
+
+	return row, nil
+}
@@ -0,0 +1,352 @@
+package cliui_test
+
+import (
+	"fmt"
+	"log"
+	"strings"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/cliui"
+)
+
+type stringWrapper struct {
+	str string
+}
+
+var _ fmt.Stringer = stringWrapper{}
+
+func (s stringWrapper) String() string {
+	return s.str
+}
+
+type tableTest1 struct {
+	Name        string      `table:"name"`
+	NotIncluded string      // no table tag
+	Age         int         `table:"age"`
+	Roles       []string    `table:"roles"`
+	Sub1        tableTest2  `table:"sub_1,recursive"`
+	Sub2        *tableTest2 `table:"sub_2,recursive"`
+	Sub3        tableTest3  `table:"sub 3,recursive"`
+	Sub4        tableTest2  `table:"sub 4"` // not recursive
+
+	// Types with special formatting.
+	Time    time.Time  `table:"time"`
+	TimePtr *time.Time `table:"time_ptr"`
+}
+
+type tableTest2 struct {
+	Name        stringWrapper `table:"name"`
+	Age         int           `table:"age"`
+	NotIncluded string        `table:"-"`
+}
+
+type tableTest3 struct {
+	NotIncluded string     // no table tag
+	Sub         tableTest2 `table:"inner,recursive"`
+}
+
+func Test_DisplayTable(t *testing.T) {
+	t.Parallel()
+
+	someTime := time.Date(2022, 8, 2, 15, 49, 10, 0, time.Local)
+	in := []tableTest1{
+		{
+			Name:  "foo",
+			Age:   10,
+			Roles: []string{"a", "b", "c"},
+			Sub1: tableTest2{
+				Name: stringWrapper{str: "foo1"},
+				Age:  11,
+			},
+			Sub2: &tableTest2{
+				Name: stringWrapper{str: "foo2"},
+				Age:  12,
+			},
+			Sub3: tableTest3{
+				Sub: tableTest2{
+					Name: stringWrapper{str: "foo3"},
+					Age:  13,
+				},
+			},
+			Sub4: tableTest2{
+				Name: stringWrapper{str: "foo4"},
+				Age:  14,
+			},
+			Time:    someTime,
+			TimePtr: &someTime,
+		},
+		{
+			Name:  "bar",
+			Age:   20,
+			Roles: []string{"a"},
+			Sub1: tableTest2{
+				Name: stringWrapper{str: "bar1"},
+				Age:  21,
+			},
+			Sub2: nil,
+			Sub3: tableTest3{
+				Sub: tableTest2{
+					Name: stringWrapper{str: "bar3"},
+					Age:  23,
+				},
+			},
+			Sub4: tableTest2{
+				Name: stringWrapper{str: "bar4"},
+				Age:  24,
+			},
+			Time:    someTime,
+			TimePtr: nil,
+		},
+		{
+			Name:  "baz",
+			Age:   30,
+			Roles: nil,
+			Sub1: tableTest2{
+				Name: stringWrapper{str: "baz1"},
+				Age:  31,
+			},
+			Sub2: nil,
+			Sub3: tableTest3{
+				Sub: tableTest2{
+					Name: stringWrapper{str: "baz3"},
+					Age:  33,
+				},
+			},
+			Sub4: tableTest2{
+				Name: stringWrapper{str: "baz4"},
+				Age:  34,
+			},
+			Time:    someTime,
+			TimePtr: nil,
+		},
+	}
+
+	// This test tests skipping fields without table tags, recursion, pointer
+	// dereferencing, and nil pointer skipping.
+	t.Run("OK", func(t *testing.T) {
+		t.Parallel()
+
+		expected := `
+NAME  AGE  ROLES    SUB 1 NAME  SUB 1 AGE  SUB 2 NAME  SUB 2 AGE  SUB 3 INNER NAME  SUB 3 INNER AGE  SUB 4       TIME             TIME PTR
+foo    10  [a b c]  foo1               11  foo2        12         foo3                           13  {foo4 14 }  Aug  2 15:49:10  Aug  2 15:49:10
+bar    20  [a]      bar1               21  <nil>       <nil>      bar3                           23  {bar4 24 }  Aug  2 15:49:10  <nil>
+baz    30  []       baz1               31  <nil>       <nil>      baz3                           33  {baz4 34 }  Aug  2 15:49:10  <nil>
+		`
+
+		// Test with non-pointer values.
+		out, err := cliui.DisplayTable(in, "", nil)
+		log.Println("rendered table:\n" + out)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+
+		// Test with pointer values.
+		inPtr := make([]*tableTest1, len(in))
+		for i, v := range in {
+			v := v
+			inPtr[i] = &v
+		}
+		out, err = cliui.DisplayTable(inPtr, "", nil)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+	})
+
+	t.Run("Sort", func(t *testing.T) {
+		t.Parallel()
+
+		expected := `
+NAME  AGE  ROLES    SUB 1 NAME  SUB 1 AGE  SUB 2 NAME  SUB 2 AGE  SUB 3 INNER NAME  SUB 3 INNER AGE  SUB 4       TIME             TIME PTR
+bar    20  [a]      bar1               21  <nil>       <nil>      bar3                           23  {bar4 24 }  Aug  2 15:49:10  <nil>
+baz    30  []       baz1               31  <nil>       <nil>      baz3                           33  {baz4 34 }  Aug  2 15:49:10  <nil>
+foo    10  [a b c]  foo1               11  foo2        12         foo3                           13  {foo4 14 }  Aug  2 15:49:10  Aug  2 15:49:10
+		`
+
+		out, err := cliui.DisplayTable(in, "name", nil)
+		log.Println("rendered table:\n" + out)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+	})
+
+	t.Run("Filter", func(t *testing.T) {
+		t.Parallel()
+
+		expected := `
+NAME  SUB 1 NAME  SUB 3 INNER NAME  TIME
+foo   foo1        foo3              Aug  2 15:49:10
+bar   bar1        bar3              Aug  2 15:49:10
+baz   baz1        baz3              Aug  2 15:49:10
+		`
+
+		out, err := cliui.DisplayTable(in, "", []string{"name", "sub_1_name", "sub_3 inner name", "time"})
+		log.Println("rendered table:\n" + out)
+		require.NoError(t, err)
+		compareTables(t, expected, out)
+	})
+
+	// This test ensures that safeties against invalid use of `table` tags
+	// causes errors (even without data).
+	t.Run("Errors", func(t *testing.T) {
+		t.Parallel()
+
+		t.Run("NotSlice", func(t *testing.T) {
+			t.Parallel()
+
+			var in string
+			_, err := cliui.DisplayTable(in, "", nil)
+			require.Error(t, err)
+		})
+
+		t.Run("BadSortColumn", func(t *testing.T) {
+			t.Parallel()
+
+			_, err := cliui.DisplayTable(in, "bad_column_does_not_exist", nil)
+			require.Error(t, err)
+		})
+
+		t.Run("BadFilterColumns", func(t *testing.T) {
+			t.Parallel()
+
+			_, err := cliui.DisplayTable(in, "", []string{"name", "bad_column_does_not_exist"})
+			require.Error(t, err)
+		})
+
+		t.Run("Interfaces", func(t *testing.T) {
+			t.Parallel()
+
+			t.Run("WithoutData", func(t *testing.T) {
+				t.Parallel()
+
+				var in []any
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+
+			t.Run("WithData", func(t *testing.T) {
+				t.Parallel()
+
+				in := []any{tableTest1{}}
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+		})
+
+		t.Run("NotStruct", func(t *testing.T) {
+			t.Parallel()
+
+			t.Run("WithoutData", func(t *testing.T) {
+				t.Parallel()
+
+				var in []string
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+
+			t.Run("WithData", func(t *testing.T) {
+				t.Parallel()
+
+				in := []string{"foo", "bar", "baz"}
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+		})
+
+		t.Run("NoTableTags", func(t *testing.T) {
+			t.Parallel()
+
+			type noTableTagsTest struct {
+				Field string `json:"field"`
+			}
+
+			t.Run("WithoutData", func(t *testing.T) {
+				t.Parallel()
+
+				var in []noTableTagsTest
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+
+			t.Run("WithData", func(t *testing.T) {
+				t.Parallel()
+
+				in := []noTableTagsTest{{Field: "hi"}}
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+		})
+
+		t.Run("InvalidTag/NoName", func(t *testing.T) {
+			t.Parallel()
+
+			type noNameTest struct {
+				Field string `table:""`
+			}
+
+			t.Run("WithoutData", func(t *testing.T) {
+				t.Parallel()
+
+				var in []noNameTest
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+
+			t.Run("WithData", func(t *testing.T) {
+				t.Parallel()
+
+				in := []noNameTest{{Field: "test"}}
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+		})
+
+		t.Run("InvalidTag/BadSyntax", func(t *testing.T) {
+			t.Parallel()
+
+			type invalidSyntaxTest struct {
+				Field string `table:"asda,asdjada"`
+			}
+
+			t.Run("WithoutData", func(t *testing.T) {
+				t.Parallel()
+
+				var in []invalidSyntaxTest
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+
+			t.Run("WithData", func(t *testing.T) {
+				t.Parallel()
+
+				in := []invalidSyntaxTest{{Field: "test"}}
+				_, err := cliui.DisplayTable(in, "", nil)
+				require.Error(t, err)
+			})
+		})
+	})
+}
+
+// compareTables normalizes the incoming table lines
+func compareTables(t *testing.T, expected, out string) {
+	t.Helper()
+
+	expectedLines := strings.Split(strings.TrimSpace(expected), "\n")
+	gotLines := strings.Split(strings.TrimSpace(out), "\n")
+	assert.Equal(t, len(expectedLines), len(gotLines), "expected line count does not match generated line count")
+
+	// Map the expected and got lines to normalize them.
+	expectedNormalized := make([]string, len(expectedLines))
+	gotNormalized := make([]string, len(gotLines))
+	normalizeLine := func(s string) string {
+		return strings.Join(strings.Fields(strings.TrimSpace(s)), " ")
+	}
+	for i, s := range expectedLines {
+		expectedNormalized[i] = normalizeLine(s)
+	}
+	for i, s := range gotLines {
+		gotNormalized[i] = normalizeLine(s)
+	}
+
+	require.Equal(t, expectedNormalized, gotNormalized, "expected lines to match generated lines")
+}
@@ -57,13 +57,6 @@ func (o sshConfigOptions) equal(other sshConfigOptions) bool {
 	return slices.Equal(opt1, opt2)
 }

-func (o sshConfigOptions) asArgs() (args []string) {
-	for _, opt := range o.sshOptions {
-		args = append(args, "--ssh-option", fmt.Sprintf("%q", opt))
-	}
-	return args
-}
-
 func (o sshConfigOptions) asList() (list []string) {
 	for _, opt := range o.sshOptions {
 		list = append(list, fmt.Sprintf("ssh-option: %s", opt))
@@ -96,18 +89,23 @@ func sshFetchWorkspaceConfigs(ctx context.Context, client *codersdk.Client) ([]s
 			}

 			wc := sshWorkspaceConfig{Name: workspace.Name}
+			var agents []codersdk.WorkspaceAgent
 			for _, resource := range resources {
 				if resource.Transition != codersdk.WorkspaceTransitionStart {
 					continue
 				}
-				for _, agent := range resource.Agents {
-					hostname := workspace.Name
-					if len(resource.Agents) > 1 {
-						hostname += "." + agent.Name
-					}
-					wc.Hosts = append(wc.Hosts, hostname)
-				}
+				agents = append(agents, resource.Agents...)
 			}
+
+			// handle both WORKSPACE and WORKSPACE.AGENT syntax
+			if len(agents) == 1 {
+				wc.Hosts = append(wc.Hosts, workspace.Name)
+			}
+			for _, agent := range agents {
+				hostname := workspace.Name + "." + agent.Name
+				wc.Hosts = append(wc.Hosts, hostname)
+			}
+
 			workspaceConfigs[i] = wc

 			return nil
@@ -139,33 +137,27 @@ func configSSH() *cobra.Command {
 		sshConfigFile    string
 		sshConfigOpts    sshConfigOptions
 		usePreviousOpts  bool
-		coderConfigFile  string
-		showDiff         bool
+		dryRun           bool
 		skipProxyCommand bool
-
-		// Diff should exit with status 1 when files differ.
-		filesDiffer bool
+		wireguard        bool
 	)
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "config-ssh",
 		Short:       "Populate your SSH config with Host entries for all of your workspaces",
-		Example: `
-  - You can use -o (or --ssh-option) so set SSH options to be used for all your
-    workspaces.
-
-    ` + cliui.Styles.Code.Render("$ coder config-ssh -o ForwardAgent=yes") + `
-
-  - You can use -D (or --diff) to display the changes that will be made.
-
-    ` + cliui.Styles.Code.Render("$ coder config-ssh --diff"),
-		PostRun: func(cmd *cobra.Command, args []string) {
-			if showDiff && filesDiffer {
-				os.Exit(1) //nolint: revive
-			}
-		},
-		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+		Example: formatExamples(
+			example{
+				Description: "You can use -o (or --ssh-option) so set SSH options to be used for all your workspaces",
+				Command:     "coder config-ssh -o ForwardAgent=yes",
+			},
+			example{
+				Description: "You can use --dry-run (or -n) to see the changes that would be made",
+				Command:     "coder config-ssh --dry-run",
+			},
+		),
+		Args: cobra.ExactArgs(0),
+		RunE: func(cmd *cobra.Command, _ []string) error {
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -173,7 +165,9 @@ func configSSH() *cobra.Command {
 			recvWorkspaceConfigs := sshPrepareWorkspaceConfigs(cmd.Context(), client)

 			out := cmd.OutOrStdout()
-			if showDiff {
+			if dryRun {
+				// Print everything except diff to stderr so
+				// that it's possible to capture the diff.
 				out = cmd.OutOrStderr()
 			}
 			binaryFile, err := currentBinPath(out)
@@ -186,7 +180,6 @@ func configSSH() *cobra.Command {
 				return xerrors.Errorf("user home dir failed: %w", err)
 			}

-			sshConfigFileOrig := sshConfigFile
 			if strings.HasPrefix(sshConfigFile, "~/") {
 				sshConfigFile = filepath.Join(homedir, sshConfigFile[2:])
 			}
@@ -204,15 +197,7 @@ func configSSH() *cobra.Command {
 			// Parse the previous configuration only if config-ssh
 			// has been run previously.
 			var lastConfig *sshConfigOptions
-			var ok bool
-			var coderConfigRaw []byte
-			if coderConfigFile, coderConfigRaw, ok = readDeprecatedCoderConfigFile(homedir, coderConfigFile); ok {
-				// Deprecated: Remove after migration period.
-				changes = append(changes, fmt.Sprintf("Remove old auto-generated coder config file at %s", coderConfigFile))
-				// Backwards compate, restore old options.
-				c := sshConfigParseLastOptions(bytes.NewReader(coderConfigRaw))
-				lastConfig = &c
-			} else if section, ok := sshConfigGetCoderSection(configRaw); ok {
+			if section, ok := sshConfigGetCoderSection(configRaw); ok {
 				c := sshConfigParseLastOptions(bytes.NewReader(section))
 				lastConfig = &c
 			}
@@ -221,7 +206,7 @@ func configSSH() *cobra.Command {
 			// or when a previous config does not exist.
 			if usePreviousOpts && lastConfig != nil {
 				sshConfigOpts = *lastConfig
-			} else if !showDiff && lastConfig != nil && !sshConfigOpts.equal(*lastConfig) {
+			} else if lastConfig != nil && !sshConfigOpts.equal(*lastConfig) {
 				newOpts := sshConfigOpts.asList()
 				newOptsMsg := "\n\n  New options: none"
 				if len(newOpts) > 0 {
@@ -243,19 +228,16 @@ func configSSH() *cobra.Command {
 					}
 					// Selecting "no" will use the last config.
 					sshConfigOpts = *lastConfig
+				} else {
+					changes = append(changes, "Use new SSH options")
+				}
+				// Only print when prompts are shown.
+				if yes, _ := cmd.Flags().GetBool("yes"); !yes {
+					_, _ = fmt.Fprint(out, "\n")
 				}
-				_, _ = fmt.Fprint(out, "\n")
 			}

 			configModified := configRaw
-
-			// Check for the presence of the coder Include
-			// statement is present and add if missing.
-			// Deprecated: Remove after migration period.
-			if configModified, ok = removeDeprecatedSSHIncludeStatement(configModified); ok {
-				changes = append(changes, fmt.Sprintf("Remove %q from %s", "Include coder", sshConfigFile))
-			}
-
 			root := createConfig(cmd)

 			buf := &bytes.Buffer{}
@@ -298,7 +280,11 @@ func configSSH() *cobra.Command {
 						"\tLogLevel ERROR",
 					)
 					if !skipProxyCommand {
-						configOptions = append(configOptions, fmt.Sprintf("\tProxyCommand %q --global-config %q ssh --stdio %s", binaryFile, root, hostname))
+						if !wireguard {
+							configOptions = append(configOptions, fmt.Sprintf("\tProxyCommand %q --global-config %q ssh --stdio %s", binaryFile, root, hostname))
+						} else {
+							configOptions = append(configOptions, fmt.Sprintf("\tProxyCommand %q --global-config %q ssh --wireguard --stdio %s", binaryFile, root, hostname))
+						}
 					}

 					_, _ = buf.WriteString(strings.Join(configOptions, "\n"))
@@ -312,96 +298,69 @@ func configSSH() *cobra.Command {
 			_, _ = buf.Write(after)

 			if !bytes.Equal(configModified, buf.Bytes()) {
-				changes = append(changes, fmt.Sprintf("Update coder config section in %s", sshConfigFile))
+				changes = append(changes, fmt.Sprintf("Update the coder section in %s", sshConfigFile))
 				configModified = buf.Bytes()
 			}

-			if showDiff {
-				if len(changes) > 0 {
-					// Write to stderr to avoid dirtying the diff output.
-					_, _ = fmt.Fprint(out, "The following changes will be made to your SSH configuration:\n\n")
-					for _, change := range changes {
-						_, _ = fmt.Fprintf(out, "  * %s\n", change)
-					}
-				}
+			if len(changes) == 0 {
+				_, _ = fmt.Fprintf(out, "No changes to make.\n")
+				return nil
+			}
+
+			if dryRun {
+				_, _ = fmt.Fprintf(out, "Dry run, the following changes would be made to your SSH configuration:\n\n  * %s\n\n", strings.Join(changes, "\n  * "))

 				color := isTTYOut(cmd)
-				diffFns := []func() ([]byte, error){
-					func() ([]byte, error) { return diffBytes(sshConfigFile, configRaw, configModified, color) },
+				diff, err := diffBytes(sshConfigFile, configRaw, configModified, color)
+				if err != nil {
+					return xerrors.Errorf("diff failed: %w", err)
 				}
-				if len(coderConfigRaw) > 0 {
-					// Deprecated: Remove after migration period.
-					diffFns = append(diffFns, func() ([]byte, error) { return diffBytes(coderConfigFile, coderConfigRaw, nil, color) })
-				}
-
-				for _, diffFn := range diffFns {
-					diff, err := diffFn()
-					if err != nil {
-						return xerrors.Errorf("diff failed: %w", err)
-					}
-					if len(diff) > 0 {
-						filesDiffer = true
-						// Always write to stdout.
-						_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\n%s", diff)
-					}
+				if len(diff) > 0 {
+					// Write diff to stdout.
+					_, _ = fmt.Fprintf(cmd.OutOrStdout(), "%s", diff)
 				}

 				return nil
 			}

 			if len(changes) > 0 {
-				// In diff mode we don't prompt re-using the previous
-				// configuration, so we output the entire command.
-				var args []string
-				if sshConfigFileOrig != sshDefaultConfigFileName {
-					args = append(args, "--ssh-config-file", sshConfigFileOrig)
-				}
-				args = append(args, sshConfigOpts.asArgs()...)
-				args = append(args, "--diff")
-				diffCommand := fmt.Sprintf("$ %s %s", cmd.CommandPath(), strings.Join(args, " "))
 				_, err = cliui.Prompt(cmd, cliui.PromptOptions{
-					Text:      fmt.Sprintf("The following changes will be made to your SSH configuration:\n\n    * %s\n\n  To see changes, run diff:\n\n    %s\n\n  Continue?", strings.Join(changes, "\n    * "), diffCommand),
+					Text:      fmt.Sprintf("The following changes will be made to your SSH configuration:\n\n    * %s\n\n  Continue?", strings.Join(changes, "\n    * ")),
 					IsConfirm: true,
 				})
 				if err != nil {
 					return nil
 				}
-				_, _ = fmt.Fprint(out, "\n")
-
-				if !bytes.Equal(configRaw, configModified) {
-					err = writeWithTempFileAndMove(sshConfigFile, bytes.NewReader(configModified))
-					if err != nil {
-						return xerrors.Errorf("write ssh config failed: %w", err)
-					}
+				// Only print when prompts are shown.
+				if yes, _ := cmd.Flags().GetBool("yes"); !yes {
+					_, _ = fmt.Fprint(out, "\n")
 				}
-				// Deprecated: Remove after migration period.
-				if len(coderConfigRaw) > 0 {
-					err = os.Remove(coderConfigFile)
-					if err != nil {
-						return xerrors.Errorf("remove coder config failed: %w", err)
-					}
+			}
+
+			if !bytes.Equal(configRaw, configModified) {
+				err = writeWithTempFileAndMove(sshConfigFile, bytes.NewReader(configModified))
+				if err != nil {
+					return xerrors.Errorf("write ssh config failed: %w", err)
 				}
 			}

 			if len(workspaceConfigs) > 0 {
 				_, _ = fmt.Fprintln(out, "You should now be able to ssh into your workspace.")
-				_, _ = fmt.Fprintf(out, "For example, try running:\n\n\t$ ssh coder.%s\n\n", workspaceConfigs[0].Name)
+				_, _ = fmt.Fprintf(out, "For example, try running:\n\n\t$ ssh coder.%s\n", workspaceConfigs[0].Name)
 			} else {
-				_, _ = fmt.Fprint(out, "You don't have any workspaces yet, try creating one with:\n\n\t$ coder create <workspace>\n\n")
+				_, _ = fmt.Fprint(out, "You don't have any workspaces yet, try creating one with:\n\n\t$ coder create <workspace>\n")
 			}
 			return nil
 		},
 	}
 	cliflag.StringVarP(cmd.Flags(), &sshConfigFile, "ssh-config-file", "", "CODER_SSH_CONFIG_FILE", sshDefaultConfigFileName, "Specifies the path to an SSH config.")
 	cmd.Flags().StringArrayVarP(&sshConfigOpts.sshOptions, "ssh-option", "o", []string{}, "Specifies additional SSH options to embed in each host stanza.")
-	cmd.Flags().BoolVarP(&showDiff, "diff", "D", false, "Show diff of changes that will be made.")
+	cmd.Flags().BoolVarP(&dryRun, "dry-run", "n", false, "Perform a trial run with no changes made, showing a diff at the end.")
 	cmd.Flags().BoolVarP(&skipProxyCommand, "skip-proxy-command", "", false, "Specifies whether the ProxyCommand option should be skipped. Useful for testing.")
 	_ = cmd.Flags().MarkHidden("skip-proxy-command")
 	cliflag.BoolVarP(cmd.Flags(), &usePreviousOpts, "use-previous-options", "", "CODER_SSH_USE_PREVIOUS_OPTIONS", false, "Specifies whether or not to keep options from previous run of config-ssh.")
-
-	// Deprecated: Remove after migration period.
-	cmd.Flags().StringVar(&coderConfigFile, "test.ssh-coder-config-file", sshDefaultCoderConfigFileName, "Specifies the path to an Coder SSH config file. Useful for testing.")
-	_ = cmd.Flags().MarkHidden("test.ssh-coder-config-file")
+	cliflag.BoolVarP(cmd.Flags(), &wireguard, "wireguard", "", "CODER_CONFIG_SSH_WIREGUARD", false, "Whether to use Wireguard for SSH tunneling.")
+	_ = cmd.Flags().MarkHidden("wireguard")

 	cliui.AllowSkipPrompt(cmd)

@@ -563,19 +522,19 @@ func currentBinPath(w io.Writer) (string, error) {
 		_, _ = fmt.Fprint(w, "\n")
 	}

-	return binName, nil
+	return exePath, nil
 }

 // diffBytes takes two byte slices and diffs them as if they were in a
 // file named name.
-//nolint: revive // Color is an option, not a control coupling.
+// nolint: revive // Color is an option, not a control coupling.
 func diffBytes(name string, b1, b2 []byte, color bool) ([]byte, error) {
 	var buf bytes.Buffer
 	var opts []write.Option
 	if color {
 		opts = append(opts, write.TerminalColor())
 	}
-	err := diff.Text(name, name+".new", b1, b2, &buf, opts...)
+	err := diff.Text(name, name, b1, b2, &buf, opts...)
 	if err != nil {
 		return nil, err
 	}
@@ -584,7 +543,7 @@ func diffBytes(name string, b1, b2 []byte, color bool) ([]byte, error) {
 	//
 	// Example:
 	// 	--- /home/user/.ssh/config
-	// 	+++ /home/user/.ssh/config.new
+	// 	+++ /home/user/.ssh/config
 	if bytes.Count(b, []byte{'\n'}) == 2 {
 		b = nil
 	}
@@ -1,66 +0,0 @@
-package cli
-
-import (
-	"bytes"
-	"os"
-	"path/filepath"
-	"regexp"
-	"strings"
-)
-
-// This file contains config-ssh definitions that are deprecated, they
-// will be removed after a migratory period.
-
-const (
-	sshDefaultCoderConfigFileName = "~/.ssh/coder"
-	sshCoderConfigHeader          = "# This file is managed by coder. DO NOT EDIT."
-)
-
-// Regular expressions are used because SSH configs do not have
-// meaningful indentation and keywords are case-insensitive.
-var (
-	// Find the semantically correct include statement. Since the user can
-	// modify their configuration as they see fit, there could be:
-	// - Leading indentation (space, tab)
-	// - Trailing indentation (space, tab)
-	// - Select newline after Include statement for cleaner removal
-	// In the following cases, we will not recognize the Include statement
-	// and leave as-is (i.e. they're not supported):
-	// - User adds another file to the Include statement
-	// - User adds a comment on the same line as the Include statement
-	sshCoderIncludedRe = regexp.MustCompile(`(?m)^[\t ]*((?i)Include) coder[\t ]*[\r]?[\n]?$`)
-)
-
-// removeDeprecatedSSHIncludeStatement checks for the Include coder statement
-// and returns modified = true if it was removed.
-func removeDeprecatedSSHIncludeStatement(data []byte) (modifiedData []byte, modified bool) {
-	coderInclude := sshCoderIncludedRe.FindIndex(data)
-	if coderInclude == nil {
-		return data, false
-	}
-
-	// Remove Include statement.
-	d := append([]byte{}, data[:coderInclude[0]]...)
-	d = append(d, data[coderInclude[1]:]...)
-	data = d
-
-	return data, true
-}
-
-// readDeprecatedCoderConfigFile reads the deprecated split config file.
-func readDeprecatedCoderConfigFile(homedir, coderConfigFile string) (name string, data []byte, ok bool) {
-	if strings.HasPrefix(coderConfigFile, "~/") {
-		coderConfigFile = filepath.Join(homedir, coderConfigFile[2:])
-	}
-
-	b, err := os.ReadFile(coderConfigFile)
-	if err != nil {
-		return coderConfigFile, nil, false
-	}
-	if len(b) > 0 {
-		if !bytes.HasPrefix(b, []byte(sshCoderConfigHeader)) {
-			return coderConfigFile, nil, false
-		}
-	}
-	return coderConfigFile, b, true
-}
@@ -1,10 +1,11 @@
 package cli_test

 import (
+	"bufio"
+	"bytes"
 	"context"
 	"fmt"
 	"io"
-	"io/fs"
 	"net"
 	"os"
 	"os/exec"
@@ -28,15 +29,14 @@ import (
 	"github.com/coder/coder/pty/ptytest"
 )

-func sshConfigFileNames(t *testing.T) (sshConfig string, coderConfig string) {
+func sshConfigFileName(t *testing.T) (sshConfig string) {
 	t.Helper()
 	tmpdir := t.TempDir()
 	dotssh := filepath.Join(tmpdir, ".ssh")
 	err := os.Mkdir(dotssh, 0o700)
 	require.NoError(t, err)
-	n1 := filepath.Join(dotssh, "config")
-	n2 := filepath.Join(dotssh, "coder")
-	return n1, n2
+	n := filepath.Join(dotssh, "config")
+	return n
 }

 func sshConfigFileCreate(t *testing.T, name string, data io.Reader) {
@@ -107,9 +107,9 @@ func TestConfigSSH(t *testing.T) {
 	agentCloser := agent.New(agentClient.ListenWorkspaceAgent, &agent.Options{
 		Logger: slogtest.Make(t, nil),
 	})
-	t.Cleanup(func() {
+	defer func() {
 		_ = agentCloser.Close()
-	})
+	}()
 	resources := coderdtest.AwaitWorkspaceAgents(t, client, workspace.LatestBuild.ID)
 	agentConn, err := client.DialWorkspaceAgent(context.Background(), resources[0].Agents[0].ID, nil)
 	require.NoError(t, err)
@@ -117,9 +117,9 @@ func TestConfigSSH(t *testing.T) {

 	listener, err := net.Listen("tcp", "127.0.0.1:0")
 	require.NoError(t, err)
-	t.Cleanup(func() {
+	defer func() {
 		_ = listener.Close()
-	})
+	}()
 	go func() {
 		for {
 			conn, err := listener.Accept()
@@ -132,11 +132,8 @@ func TestConfigSSH(t *testing.T) {
 			go io.Copy(ssh, conn)
 		}
 	}()
-	t.Cleanup(func() {
-		_ = listener.Close()
-	})

-	sshConfigFile, _ := sshConfigFileNames(t)
+	sshConfigFile := sshConfigFileName(t)

 	tcpAddr, valid := listener.Addr().(*net.TCPAddr)
 	require.True(t, valid)
@@ -171,9 +168,10 @@ func TestConfigSSH(t *testing.T) {
 	home := filepath.Dir(filepath.Dir(sshConfigFile))
 	// #nosec
 	sshCmd := exec.Command("ssh", "-F", sshConfigFile, "coder."+workspace.Name, "echo", "test")
+	pty = ptytest.New(t)
 	// Set HOME because coder config is included from ~/.ssh/coder.
 	sshCmd.Env = append(sshCmd.Env, fmt.Sprintf("HOME=%s", home))
-	sshCmd.Stderr = os.Stderr
+	sshCmd.Stderr = pty.Output()
 	data, err := sshCmd.Output()
 	require.NoError(t, err)
 	require.Equal(t, "test", strings.TrimSpace(string(data)))
@@ -197,12 +195,10 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 	}, "\n")

 	type writeConfig struct {
-		ssh   string
-		coder string
+		ssh string
 	}
 	type wantConfig struct {
-		ssh       string
-		coderKept bool
+		ssh string
 	}
 	type match struct {
 		match, write string
@@ -494,74 +490,13 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				"--yes",
 			},
 		},
-
-		// Tests for deprecated split coder config.
 		{
-			name: "Do not overwrite unknown coder config",
+			name: "Do not overwrite config when using --dry-run",
 			writeConfig: writeConfig{
 				ssh: strings.Join([]string{
 					baseHeader,
 					"",
 				}, "\n"),
-				coder: strings.Join([]string{
-					"We're no strangers to love",
-					"You know the rules and so do I (do I)",
-				}, "\n"),
-			},
-			wantConfig: wantConfig{
-				coderKept: true,
-			},
-		},
-		{
-			name: "Transfer options from coder to ssh config",
-			writeConfig: writeConfig{
-				ssh: strings.Join([]string{
-					"Include coder",
-					"",
-				}, "\n"),
-				coder: strings.Join([]string{
-					"# This file is managed by coder. DO NOT EDIT.",
-					"#",
-					"# You should not hand-edit this file, all changes will be lost when running",
-					"# \"coder config-ssh\".",
-					"#",
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-				}, "\n"),
-			},
-			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
-			},
-			matches: []match{
-				{match: "Use new options?", write: "no"},
-				{match: "Continue?", write: "yes"},
-			},
-		},
-		{
-			name: "Allow overwriting previous options from coder config",
-			writeConfig: writeConfig{
-				ssh: strings.Join([]string{
-					"Include coder",
-					"",
-				}, "\n"),
-				coder: strings.Join([]string{
-					"# This file is managed by coder. DO NOT EDIT.",
-					"#",
-					"# You should not hand-edit this file, all changes will be lost when running",
-					"# \"coder config-ssh\".",
-					"#",
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-				}, "\n"),
 			},
 			wantConfig: wantConfig{
 				ssh: strings.Join([]string{
@@ -569,43 +504,10 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 					"",
 				}, "\n"),
 			},
-			matches: []match{
-				{match: "Use new options?", write: "yes"},
-				{match: "Continue?", write: "yes"},
-			},
-		},
-		{
-			name: "Allow overwriting previous options from coder config when they differ",
-			writeConfig: writeConfig{
-				ssh: strings.Join([]string{
-					"Include coder",
-					"",
-				}, "\n"),
-				coder: strings.Join([]string{
-					"# This file is managed by coder. DO NOT EDIT.",
-					"#",
-					"# You should not hand-edit this file, all changes will be lost when running",
-					"# \"coder config-ssh\".",
-					"#",
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=yes",
-					"#",
-				}, "\n"),
-			},
-			wantConfig: wantConfig{
-				ssh: strings.Join([]string{
-					headerStart,
-					"# Last config-ssh options:",
-					"# :ssh-option=ForwardAgent=no",
-					"#",
-					headerEnd,
-					"",
-				}, "\n"),
-			},
-			args: []string{"--ssh-option", "ForwardAgent=no"},
-			matches: []match{
-				{match: "Use new options?", write: "yes"},
-				{match: "Continue?", write: "yes"},
+			args: []string{
+				"--ssh-option", "ForwardAgent=yes",
+				"--dry-run",
+				"--yes",
 			},
 		},
 	}
@@ -625,18 +527,14 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 			)

 			// Prepare ssh config files.
-			sshConfigName, coderConfigName := sshConfigFileNames(t)
+			sshConfigName := sshConfigFileName(t)
 			if tt.writeConfig.ssh != "" {
 				sshConfigFileCreate(t, sshConfigName, strings.NewReader(tt.writeConfig.ssh))
 			}
-			if tt.writeConfig.coder != "" {
-				sshConfigFileCreate(t, coderConfigName, strings.NewReader(tt.writeConfig.coder))
-			}

 			args := []string{
 				"config-ssh",
 				"--ssh-config-file", sshConfigName,
-				"--test.ssh-coder-config-file", coderConfigName,
 			}
 			args = append(args, tt.args...)
 			cmd, root := clitest.New(t, args...)
@@ -665,10 +563,155 @@ func TestConfigSSH_FileWriteAndOptionsFlow(t *testing.T) {
 				got := sshConfigFileRead(t, sshConfigName)
 				assert.Equal(t, tt.wantConfig.ssh, got)
 			}
-			if !tt.wantConfig.coderKept {
-				_, err := os.ReadFile(coderConfigName)
-				assert.ErrorIs(t, err, fs.ErrNotExist)
-			}
 		})
 	}
 }
+
+func TestConfigSSH_Hostnames(t *testing.T) {
+	t.Parallel()
+
+	type resourceSpec struct {
+		name   string
+		agents []string
+	}
+	tests := []struct {
+		name      string
+		resources []resourceSpec
+		expected  []string
+	}{
+		{
+			name: "one resource with one agent",
+			resources: []resourceSpec{
+				{name: "foo", agents: []string{"agent1"}},
+			},
+			expected: []string{"coder.@", "coder.@.agent1"},
+		},
+		{
+			name: "one resource with two agents",
+			resources: []resourceSpec{
+				{name: "foo", agents: []string{"agent1", "agent2"}},
+			},
+			expected: []string{"coder.@.agent1", "coder.@.agent2"},
+		},
+		{
+			name: "two resources with one agent",
+			resources: []resourceSpec{
+				{name: "foo", agents: []string{"agent1"}},
+				{name: "bar"},
+			},
+			expected: []string{"coder.@", "coder.@.agent1"},
+		},
+		{
+			name: "two resources with two agents",
+			resources: []resourceSpec{
+				{name: "foo", agents: []string{"agent1"}},
+				{name: "bar", agents: []string{"agent2"}},
+			},
+			expected: []string{"coder.@.agent1", "coder.@.agent2"},
+		},
+	}
+
+	for _, tt := range tests {
+		tt := tt
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			var resources []*proto.Resource
+			for _, resourceSpec := range tt.resources {
+				resource := &proto.Resource{
+					Name: resourceSpec.name,
+					Type: "aws_instance",
+				}
+				for _, agentName := range resourceSpec.agents {
+					resource.Agents = append(resource.Agents, &proto.Agent{
+						Id:   uuid.NewString(),
+						Name: agentName,
+					})
+				}
+				resources = append(resources, resource)
+			}
+
+			provisionResponse := []*proto.Provision_Response{{
+				Type: &proto.Provision_Response_Complete{
+					Complete: &proto.Provision_Complete{
+						Resources: resources,
+					},
+				},
+			}}
+
+			client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+			user := coderdtest.CreateFirstUser(t, client)
+			// authToken := uuid.NewString()
+			version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
+				Parse:           echo.ParseComplete,
+				ProvisionDryRun: provisionResponse,
+				Provision:       provisionResponse,
+			})
+			coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+			template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+			workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+			coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
+
+			sshConfigFile := sshConfigFileName(t)
+
+			cmd, root := clitest.New(t, "config-ssh", "--ssh-config-file", sshConfigFile)
+			clitest.SetupConfig(t, client, root)
+			doneChan := make(chan struct{})
+			pty := ptytest.New(t)
+			cmd.SetIn(pty.Input())
+			cmd.SetOut(pty.Output())
+			go func() {
+				defer close(doneChan)
+				err := cmd.Execute()
+				assert.NoError(t, err)
+			}()
+
+			matches := []struct {
+				match, write string
+			}{
+				{match: "Continue?", write: "yes"},
+			}
+			for _, m := range matches {
+				pty.ExpectMatch(m.match)
+				pty.WriteLine(m.write)
+			}
+
+			<-doneChan
+
+			var expectedHosts []string
+			for _, hostnamePattern := range tt.expected {
+				hostname := strings.ReplaceAll(hostnamePattern, "@", workspace.Name)
+				expectedHosts = append(expectedHosts, hostname)
+			}
+
+			hosts := sshConfigFileParseHosts(t, sshConfigFile)
+			require.ElementsMatch(t, expectedHosts, hosts)
+		})
+	}
+}
+
+// sshConfigFileParseHosts reads a file in the format of .ssh/config and extracts
+// the hostnames that are listed in "Host" directives.
+func sshConfigFileParseHosts(t *testing.T, name string) []string {
+	t.Helper()
+	b, err := os.ReadFile(name)
+	require.NoError(t, err)
+
+	var result []string
+	lineScanner := bufio.NewScanner(bytes.NewBuffer(b))
+	for lineScanner.Scan() {
+		line := lineScanner.Text()
+		line = strings.TrimSpace(line)
+
+		tokenScanner := bufio.NewScanner(bytes.NewBufferString(line))
+		tokenScanner.Split(bufio.ScanWords)
+		ok := tokenScanner.Scan()
+		if ok && tokenScanner.Text() == "Host" {
+			for tokenScanner.Scan() {
+				result = append(result, tokenScanner.Text())
+			}
+		}
+	}
+
+	return result
+}
@@ -27,7 +27,7 @@ func create() *cobra.Command {
 		Use:         "create [name]",
 		Short:       "Create a workspace from a template",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -120,87 +120,11 @@ func create() *cobra.Command {
 				schedSpec = ptr.Ref(sched.String())
 			}

-			templateVersion, err := client.TemplateVersion(cmd.Context(), template.ActiveVersionID)
-			if err != nil {
-				return err
-			}
-			parameterSchemas, err := client.TemplateVersionSchema(cmd.Context(), templateVersion.ID)
-			if err != nil {
-				return err
-			}
-
-			// parameterMapFromFile can be nil if parameter file is not specified
-			var parameterMapFromFile map[string]string
-			if parameterFile != "" {
-				_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Paragraph.Render("Attempting to read the variables from the parameter file.")+"\r\n")
-				parameterMapFromFile, err = createParameterMapFromFile(parameterFile)
-				if err != nil {
-					return err
-				}
-			}
-
-			disclaimerPrinted := false
-			parameters := make([]codersdk.CreateParameterRequest, 0)
-			for _, parameterSchema := range parameterSchemas {
-				if !parameterSchema.AllowOverrideSource {
-					continue
-				}
-				if !disclaimerPrinted {
-					_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Paragraph.Render("This template has customizable parameters. Values can be changed after create, but may have unintended side effects (like data loss).")+"\r\n")
-					disclaimerPrinted = true
-				}
-				parameterValue, err := getParameterValueFromMapOrInput(cmd, parameterMapFromFile, parameterSchema)
-				if err != nil {
-					return err
-				}
-				parameters = append(parameters, codersdk.CreateParameterRequest{
-					Name:              parameterSchema.Name,
-					SourceValue:       parameterValue,
-					SourceScheme:      codersdk.ParameterSourceSchemeData,
-					DestinationScheme: parameterSchema.DefaultDestinationScheme,
-				})
-			}
-			_, _ = fmt.Fprintln(cmd.OutOrStdout())
-
-			// Run a dry-run with the given parameters to check correctness
-			after := time.Now()
-			dryRun, err := client.CreateTemplateVersionDryRun(cmd.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
-				WorkspaceName:   workspaceName,
-				ParameterValues: parameters,
-			})
-			if err != nil {
-				return xerrors.Errorf("begin workspace dry-run: %w", err)
-			}
-			_, _ = fmt.Fprintln(cmd.OutOrStdout(), "Planning workspace...")
-			err = cliui.ProvisionerJob(cmd.Context(), cmd.OutOrStdout(), cliui.ProvisionerJobOptions{
-				Fetch: func() (codersdk.ProvisionerJob, error) {
-					return client.TemplateVersionDryRun(cmd.Context(), templateVersion.ID, dryRun.ID)
-				},
-				Cancel: func() error {
-					return client.CancelTemplateVersionDryRun(cmd.Context(), templateVersion.ID, dryRun.ID)
-				},
-				Logs: func() (<-chan codersdk.ProvisionerJobLog, error) {
-					return client.TemplateVersionDryRunLogsAfter(cmd.Context(), templateVersion.ID, dryRun.ID, after)
-				},
-				// Don't show log output for the dry-run unless there's an error.
-				Silent: true,
-			})
-			if err != nil {
-				// TODO (Dean): reprompt for parameter values if we deem it to
-				// be a validation error
-				return xerrors.Errorf("dry-run workspace: %w", err)
-			}
-
-			resources, err := client.TemplateVersionDryRunResources(cmd.Context(), templateVersion.ID, dryRun.ID)
-			if err != nil {
-				return xerrors.Errorf("get workspace dry-run resources: %w", err)
-			}
-
-			err = cliui.WorkspaceResources(cmd.OutOrStdout(), resources, cliui.WorkspaceResourcesOptions{
-				WorkspaceName: workspaceName,
-				// Since agent's haven't connected yet, hiding this makes more sense.
-				HideAgentState: true,
-				Title:          "Workspace Preview",
+			parameters, err := prepWorkspaceBuild(cmd, client, prepWorkspaceBuildArgs{
+				Template:         template,
+				ExistingParams:   []codersdk.Parameter{},
+				ParameterFile:    parameterFile,
+				NewWorkspaceName: workspaceName,
 			})
 			if err != nil {
 				return err
@@ -214,6 +138,7 @@ func create() *cobra.Command {
 				return err
 			}

+			after := time.Now()
 			workspace, err := client.CreateWorkspace(cmd.Context(), organization.ID, codersdk.CreateWorkspaceRequest{
 				TemplateID:        template.ID,
 				Name:              workspaceName,
@@ -230,7 +155,7 @@ func create() *cobra.Command {
 				return err
 			}

-			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nThe %s workspace has been created!\n", cliui.Styles.Keyword.Render(workspace.Name))
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nThe %s workspace has been created at %s!\n", cliui.Styles.Keyword.Render(workspace.Name), cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
 			return nil
 		},
 	}
@@ -242,3 +167,118 @@ func create() *cobra.Command {
 	cliflag.DurationVarP(cmd.Flags(), &stopAfter, "stop-after", "", "CODER_WORKSPACE_STOP_AFTER", 8*time.Hour, "Specify a duration after which the workspace should shut down (e.g. 8h).")
 	return cmd
 }
+
+type prepWorkspaceBuildArgs struct {
+	Template         codersdk.Template
+	ExistingParams   []codersdk.Parameter
+	ParameterFile    string
+	NewWorkspaceName string
+}
+
+// prepWorkspaceBuild will ensure a workspace build will succeed on the latest template version.
+// Any missing params will be prompted to the user.
+func prepWorkspaceBuild(cmd *cobra.Command, client *codersdk.Client, args prepWorkspaceBuildArgs) ([]codersdk.CreateParameterRequest, error) {
+	ctx := cmd.Context()
+	templateVersion, err := client.TemplateVersion(ctx, args.Template.ActiveVersionID)
+	if err != nil {
+		return nil, err
+	}
+	parameterSchemas, err := client.TemplateVersionSchema(ctx, templateVersion.ID)
+	if err != nil {
+		return nil, err
+	}
+
+	// parameterMapFromFile can be nil if parameter file is not specified
+	var parameterMapFromFile map[string]string
+	useParamFile := false
+	if args.ParameterFile != "" {
+		useParamFile = true
+		_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Paragraph.Render("Attempting to read the variables from the parameter file.")+"\r\n")
+		parameterMapFromFile, err = createParameterMapFromFile(args.ParameterFile)
+		if err != nil {
+			return nil, err
+		}
+	}
+	disclaimerPrinted := false
+	parameters := make([]codersdk.CreateParameterRequest, 0)
+PromptParamLoop:
+	for _, parameterSchema := range parameterSchemas {
+		if !parameterSchema.AllowOverrideSource {
+			continue
+		}
+		if !disclaimerPrinted {
+			_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Paragraph.Render("This template has customizable parameters. Values can be changed after create, but may have unintended side effects (like data loss).")+"\r\n")
+			disclaimerPrinted = true
+		}
+
+		// Param file is all or nothing
+		if !useParamFile {
+			for _, e := range args.ExistingParams {
+				if e.Name == parameterSchema.Name {
+					// If the param already exists, we do not need to prompt it again.
+					// The workspace scope will reuse params for each build.
+					continue PromptParamLoop
+				}
+			}
+		}
+
+		parameterValue, err := getParameterValueFromMapOrInput(cmd, parameterMapFromFile, parameterSchema)
+		if err != nil {
+			return nil, err
+		}
+
+		parameters = append(parameters, codersdk.CreateParameterRequest{
+			Name:              parameterSchema.Name,
+			SourceValue:       parameterValue,
+			SourceScheme:      codersdk.ParameterSourceSchemeData,
+			DestinationScheme: parameterSchema.DefaultDestinationScheme,
+		})
+	}
+	_, _ = fmt.Fprintln(cmd.OutOrStdout())
+
+	// Run a dry-run with the given parameters to check correctness
+	after := time.Now()
+	dryRun, err := client.CreateTemplateVersionDryRun(cmd.Context(), templateVersion.ID, codersdk.CreateTemplateVersionDryRunRequest{
+		WorkspaceName:   args.NewWorkspaceName,
+		ParameterValues: parameters,
+	})
+	if err != nil {
+		return nil, xerrors.Errorf("begin workspace dry-run: %w", err)
+	}
+	_, _ = fmt.Fprintln(cmd.OutOrStdout(), "Planning workspace...")
+	err = cliui.ProvisionerJob(cmd.Context(), cmd.OutOrStdout(), cliui.ProvisionerJobOptions{
+		Fetch: func() (codersdk.ProvisionerJob, error) {
+			return client.TemplateVersionDryRun(cmd.Context(), templateVersion.ID, dryRun.ID)
+		},
+		Cancel: func() error {
+			return client.CancelTemplateVersionDryRun(cmd.Context(), templateVersion.ID, dryRun.ID)
+		},
+		Logs: func() (<-chan codersdk.ProvisionerJobLog, error) {
+			return client.TemplateVersionDryRunLogsAfter(cmd.Context(), templateVersion.ID, dryRun.ID, after)
+		},
+		// Don't show log output for the dry-run unless there's an error.
+		Silent: true,
+	})
+	if err != nil {
+		// TODO (Dean): reprompt for parameter values if we deem it to
+		// be a validation error
+		return nil, xerrors.Errorf("dry-run workspace: %w", err)
+	}
+
+	resources, err := client.TemplateVersionDryRunResources(cmd.Context(), templateVersion.ID, dryRun.ID)
+	if err != nil {
+		return nil, xerrors.Errorf("get workspace dry-run resources: %w", err)
+	}
+
+	err = cliui.WorkspaceResources(cmd.OutOrStdout(), resources, cliui.WorkspaceResourcesOptions{
+		WorkspaceName: args.NewWorkspaceName,
+		// Since agents haven't connected yet, hiding this makes more sense.
+		HideAgentState: true,
+		Title:          "Workspace Preview",
+	})
+	if err != nil {
+		return nil, err
+	}
+
+	return parameters, nil
+}
@@ -2,7 +2,6 @@ package cli_test

 import (
 	"context"
-	"database/sql"
 	"fmt"
 	"os"
 	"testing"
@@ -13,11 +12,11 @@ import (

 	"github.com/coder/coder/cli/clitest"
 	"github.com/coder/coder/coderd/coderdtest"
-	"github.com/coder/coder/coderd/database"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 func TestCreate(t *testing.T) {
@@ -90,7 +89,7 @@ func TestCreate(t *testing.T) {

 		member := coderdtest.CreateAnotherUser(t, client, user.OrganizationID)
 		clitest.SetupConfig(t, member, root)
-		cmdCtx, done := context.WithTimeout(context.Background(), time.Second*3)
+		cmdCtx, done := context.WithTimeout(context.Background(), testutil.WaitLong)
 		go func() {
 			defer done()
 			err := cmd.ExecuteContext(cmdCtx)
@@ -194,6 +193,7 @@ func TestCreate(t *testing.T) {
 		coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 		_ = coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 		tempDir := t.TempDir()
+		removeTmpDirUntilSuccessAfterTest(t, tempDir)
 		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
 		_, _ = parameterFile.WriteString("region: \"bingo\"\nusername: \"boingo\"")
 		cmd, root := clitest.New(t, "create", "", "--parameter-file", parameterFile.Name())
@@ -219,7 +219,6 @@ func TestCreate(t *testing.T) {
 			pty.WriteLine(value)
 		}
 		<-doneChan
-		removeTmpDirUntilSuccess(t, tempDir)
 	})

 	t.Run("WithParameterFileNotContainingTheValue", func(t *testing.T) {
@@ -236,6 +235,7 @@ func TestCreate(t *testing.T) {
 		coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 		tempDir := t.TempDir()
+		removeTmpDirUntilSuccessAfterTest(t, tempDir)
 		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
 		_, _ = parameterFile.WriteString("zone: \"bananas\"")
 		cmd, root := clitest.New(t, "create", "my-workspace", "--template", template.Name, "--parameter-file", parameterFile.Name())
@@ -250,43 +250,42 @@ func TestCreate(t *testing.T) {
 			assert.EqualError(t, err, "Parameter value absent in parameter file for \"region\"!")
 		}()
 		<-doneChan
-		removeTmpDirUntilSuccess(t, tempDir)
 	})

 	t.Run("FailedDryRun", func(t *testing.T) {
 		t.Parallel()
-		client, api := coderdtest.NewWithAPI(t, &coderdtest.Options{IncludeProvisionerD: true})
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
 		user := coderdtest.CreateFirstUser(t, client)
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
-			Parse: echo.ParseComplete,
+			Parse: []*proto.Parse_Response{{
+				Type: &proto.Parse_Response_Complete{
+					Complete: &proto.Parse_Complete{
+						ParameterSchemas: echo.ParameterSuccess,
+					},
+				},
+			}},
 			ProvisionDryRun: []*proto.Provision_Response{
 				{
 					Type: &proto.Provision_Response_Complete{
-						Complete: &proto.Provision_Complete{
-							Error: "test error",
-						},
+						Complete: &proto.Provision_Complete{},
 					},
 				},
 			},
 		})

+		tempDir := t.TempDir()
+		parameterFile, err := os.CreateTemp(tempDir, "testParameterFile*.yaml")
+		require.NoError(t, err)
+		defer parameterFile.Close()
+		_, _ = parameterFile.WriteString(fmt.Sprintf("%s: %q", echo.ParameterExecKey, echo.ParameterError("fail")))
+
 		// The template import job should end up failed, but we need it to be
 		// succeeded so the dry-run can begin.
 		version = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
-		require.Equal(t, codersdk.ProvisionerJobFailed, version.Job.Status, "job is not failed")
-		err := api.Database.UpdateProvisionerJobWithCompleteByID(context.Background(), database.UpdateProvisionerJobWithCompleteByIDParams{
-			ID: version.Job.ID,
-			CompletedAt: sql.NullTime{
-				Time:  time.Now(),
-				Valid: true,
-			},
-			UpdatedAt: time.Now(),
-			Error:     sql.NullString{},
-		})
-		require.NoError(t, err, "update provisioner job")
+		require.Equal(t, codersdk.ProvisionerJobSucceeded, version.Job.Status, "job is not failed")

 		_ = coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
-		cmd, root := clitest.New(t, "create", "test")
+		cmd, root := clitest.New(t, "create", "test", "--parameter-file", parameterFile.Name())
 		clitest.SetupConfig(t, client, root)
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
@@ -1,6 +1,7 @@
 package cli

 import (
+	"fmt"
 	"time"

 	"github.com/spf13/cobra"
@@ -10,7 +11,7 @@ import (
 )

 // nolint
-func delete() *cobra.Command {
+func deleteWorkspace() *cobra.Command {
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "delete <workspace>",
@@ -21,12 +22,13 @@ func delete() *cobra.Command {
 			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      "Confirm delete workspace?",
 				IsConfirm: true,
+				Default:   cliui.ConfirmNo,
 			})
 			if err != nil {
 				return err
 			}

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -41,7 +43,14 @@ func delete() *cobra.Command {
 			if err != nil {
 				return err
 			}
-			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+
+			err = cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+			if err != nil {
+				return err
+			}
+
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nThe %s workspace has been deleted at %s!\n", cliui.Styles.Keyword.Render(workspace.Name), cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
+			return nil
 		},
 	}
 	cliui.AllowSkipPrompt(cmd)
@@ -15,6 +15,7 @@ import (
 )

 func TestDelete(t *testing.T) {
+	t.Parallel()
 	t.Run("WithParameter", func(t *testing.T) {
 		t.Parallel()
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
@@ -18,14 +18,17 @@ import (
 )

 func dotfiles() *cobra.Command {
-	var (
-		symlinkDir string
-	)
+	var symlinkDir string
 	cmd := &cobra.Command{
-		Use:     "dotfiles [git_repo_url]",
-		Args:    cobra.ExactArgs(1),
-		Short:   "Checkout and install a dotfiles repository.",
-		Example: "coder dotfiles [-y] git@github.com:example/dotfiles.git",
+		Use:   "dotfiles [git_repo_url]",
+		Args:  cobra.ExactArgs(1),
+		Short: "Check out and install a dotfiles repository.",
+		Example: formatExamples(
+			example{
+				Description: "Check out and install a dotfiles repository without prompts",
+				Command:     "coder dotfiles --yes git@github.com:example/dotfiles.git",
+			},
+		),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			var (
 				dotfilesRepoDir = "dotfiles"
@@ -0,0 +1,102 @@
+package cli
+
+import (
+	"encoding/json"
+	"fmt"
+	"strings"
+
+	"github.com/spf13/cobra"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/cli/cliui"
+	"github.com/coder/coder/codersdk"
+)
+
+var featureColumns = []string{"Name", "Entitlement", "Enabled", "Limit", "Actual"}
+
+func features() *cobra.Command {
+	cmd := &cobra.Command{
+		Short:   "List features",
+		Use:     "features",
+		Aliases: []string{"feature"},
+	}
+	cmd.AddCommand(
+		featuresList(),
+	)
+	return cmd
+}
+
+func featuresList() *cobra.Command {
+	var (
+		columns      []string
+		outputFormat string
+	)
+
+	cmd := &cobra.Command{
+		Use:     "list",
+		Aliases: []string{"ls"},
+		RunE: func(cmd *cobra.Command, args []string) error {
+			client, err := CreateClient(cmd)
+			if err != nil {
+				return err
+			}
+			entitlements, err := client.Entitlements(cmd.Context())
+			if err != nil {
+				return err
+			}
+
+			out := ""
+			switch outputFormat {
+			case "table", "":
+				out, err = displayFeatures(columns, entitlements.Features)
+				if err != nil {
+					return xerrors.Errorf("render table: %w", err)
+				}
+			case "json":
+				outBytes, err := json.Marshal(entitlements)
+				if err != nil {
+					return xerrors.Errorf("marshal features to JSON: %w", err)
+				}
+
+				out = string(outBytes)
+			default:
+				return xerrors.Errorf(`unknown output format %q, only "table" and "json" are supported`, outputFormat)
+			}
+
+			_, err = fmt.Fprintln(cmd.OutOrStdout(), out)
+			return err
+		},
+	}
+
+	cmd.Flags().StringArrayVarP(&columns, "column", "c", featureColumns,
+		fmt.Sprintf("Specify a column to filter in the table. Available columns are: %s",
+			strings.Join(featureColumns, ", ")))
+	cmd.Flags().StringVarP(&outputFormat, "output", "o", "table", "Output format. Available formats are: table, json.")
+	return cmd
+}
+
+type featureRow struct {
+	Name        string `table:"name"`
+	Entitlement string `table:"entitlement"`
+	Enabled     bool   `table:"enabled"`
+	Limit       *int64 `table:"limit"`
+	Actual      *int64 `table:"actual"`
+}
+
+// displayFeatures will return a table displaying all features passed in.
+// filterColumns must be a subset of the feature fields and will determine which
+// columns to display
+func displayFeatures(filterColumns []string, features map[string]codersdk.Feature) (string, error) {
+	rows := make([]featureRow, 0, len(features))
+	for name, feat := range features {
+		rows = append(rows, featureRow{
+			Name:        name,
+			Entitlement: string(feat.Entitlement),
+			Enabled:     feat.Enabled,
+			Limit:       feat.Limit,
+			Actual:      feat.Actual,
+		})
+	}
+
+	return cliui.DisplayTable(rows, "name", filterColumns)
+}
@@ -0,0 +1,66 @@
+package cli_test
+
+import (
+	"bytes"
+	"encoding/json"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/codersdk"
+	"github.com/coder/coder/pty/ptytest"
+)
+
+func TestFeaturesList(t *testing.T) {
+	t.Parallel()
+	t.Run("Table", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		cmd, root := clitest.New(t, "features", "list")
+		clitest.SetupConfig(t, client, root)
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+		errC := make(chan error)
+		go func() {
+			errC <- cmd.Execute()
+		}()
+		require.NoError(t, <-errC)
+		pty.ExpectMatch("user_limit")
+		pty.ExpectMatch("not_entitled")
+	})
+	t.Run("JSON", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+		cmd, root := clitest.New(t, "features", "list", "-o", "json")
+		clitest.SetupConfig(t, client, root)
+		doneChan := make(chan struct{})
+
+		buf := bytes.NewBuffer(nil)
+		cmd.SetOut(buf)
+		go func() {
+			defer close(doneChan)
+			err := cmd.Execute()
+			assert.NoError(t, err)
+		}()
+
+		<-doneChan
+
+		var entitlements codersdk.Entitlements
+		err := json.Unmarshal(buf.Bytes(), &entitlements)
+		require.NoError(t, err, "unmarshal JSON output")
+		assert.Len(t, entitlements.Features, 2)
+		assert.Empty(t, entitlements.Warnings)
+		assert.Equal(t, codersdk.EntitlementNotEntitled,
+			entitlements.Features[codersdk.FeatureUserLimit].Entitlement)
+		assert.Equal(t, codersdk.EntitlementNotEntitled,
+			entitlements.Features[codersdk.FeatureAuditLog].Entitlement)
+		assert.False(t, entitlements.HasLicense)
+	})
+}
@@ -22,6 +22,7 @@ import (
 func TestGitSSH(t *testing.T) {
 	t.Parallel()
 	t.Run("Dial", func(t *testing.T) {
+		t.Parallel()
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
 		user := coderdtest.CreateFirstUser(t, client)

@@ -58,7 +59,7 @@ func TestGitSSH(t *testing.T) {
 		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

 		// start workspace agent
-		cmd, root := clitest.New(t, "agent", "--agent-token", agentToken, "--agent-url", client.URL.String())
+		cmd, root := clitest.New(t, "agent", "--agent-token", agentToken, "--agent-url", client.URL.String(), "--wireguard=false")
 		agentClient := client
 		clitest.SetupConfig(t, agentClient, root)
 		ctx, cancelFunc := context.WithCancel(context.Background())
@@ -5,7 +5,6 @@ import (
 	"time"

 	"github.com/google/uuid"
-	"github.com/jedib0t/go-pretty/v6/table"
 	"github.com/spf13/cobra"

 	"github.com/coder/coder/cli/cliui"
@@ -14,29 +13,85 @@ import (
 	"github.com/coder/coder/codersdk"
 )

+type workspaceListRow struct {
+	Workspace  string `table:"workspace"`
+	Template   string `table:"template"`
+	Status     string `table:"status"`
+	LastBuilt  string `table:"last built"`
+	Outdated   bool   `table:"outdated"`
+	StartsAt   string `table:"starts at"`
+	StopsAfter string `table:"stops after"`
+}
+
+func workspaceListRowFromWorkspace(now time.Time, usersByID map[uuid.UUID]codersdk.User, workspace codersdk.Workspace) workspaceListRow {
+	status := codersdk.WorkspaceDisplayStatus(workspace.LatestBuild.Job.Status, workspace.LatestBuild.Transition)
+
+	lastBuilt := now.UTC().Sub(workspace.LatestBuild.Job.CreatedAt).Truncate(time.Second)
+	autostartDisplay := "-"
+	if !ptr.NilOrEmpty(workspace.AutostartSchedule) {
+		if sched, err := schedule.Weekly(*workspace.AutostartSchedule); err == nil {
+			autostartDisplay = fmt.Sprintf("%s %s (%s)", sched.Time(), sched.DaysOfWeek(), sched.Location())
+		}
+	}
+
+	autostopDisplay := "-"
+	if !ptr.NilOrZero(workspace.TTLMillis) {
+		dur := time.Duration(*workspace.TTLMillis) * time.Millisecond
+		autostopDisplay = durationDisplay(dur)
+		if !workspace.LatestBuild.Deadline.IsZero() && workspace.LatestBuild.Deadline.Time.After(now) && status == "Running" {
+			remaining := time.Until(workspace.LatestBuild.Deadline.Time)
+			autostopDisplay = fmt.Sprintf("%s (%s)", autostopDisplay, relative(remaining))
+		}
+	}
+
+	user := usersByID[workspace.OwnerID]
+	return workspaceListRow{
+		Workspace:  user.Username + "/" + workspace.Name,
+		Template:   workspace.TemplateName,
+		Status:     status,
+		LastBuilt:  durationDisplay(lastBuilt),
+		Outdated:   workspace.Outdated,
+		StartsAt:   autostartDisplay,
+		StopsAfter: autostopDisplay,
+	}
+}
+
 func list() *cobra.Command {
 	var (
-		columns []string
+		columns     []string
+		searchQuery string
+		me          bool
 	)
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
 		Use:         "list",
 		Short:       "List all workspaces",
 		Aliases:     []string{"ls"},
+		Args:        cobra.ExactArgs(0),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
-			workspaces, err := client.Workspaces(cmd.Context(), codersdk.WorkspaceFilter{})
+			filter := codersdk.WorkspaceFilter{
+				FilterQuery: searchQuery,
+			}
+			if me {
+				myUser, err := client.User(cmd.Context(), codersdk.Me)
+				if err != nil {
+					return err
+				}
+				filter.Owner = myUser.Username
+			}
+			workspaces, err := client.Workspaces(cmd.Context(), filter)
 			if err != nil {
 				return err
 			}
 			if len(workspaces) == 0 {
-				_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Prompt.String()+"No workspaces found! Create one:")
-				_, _ = fmt.Fprintln(cmd.OutOrStdout())
-				_, _ = fmt.Fprintln(cmd.OutOrStdout(), "  "+cliui.Styles.Code.Render("coder create <name>"))
-				_, _ = fmt.Fprintln(cmd.OutOrStdout())
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), cliui.Styles.Prompt.String()+"No workspaces found! Create one:")
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr())
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), "  "+cliui.Styles.Code.Render("coder create <name>"))
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr())
 				return nil
 			}
 			users, err := client.Users(cmd.Context(), codersdk.UsersRequest{})
@@ -48,78 +103,24 @@ func list() *cobra.Command {
 				usersByID[user.ID] = user
 			}

-			tableWriter := cliui.Table()
-			header := table.Row{"workspace", "template", "status", "last built", "outdated", "starts at", "stops after"}
-			tableWriter.AppendHeader(header)
-			tableWriter.SortBy([]table.SortBy{{
-				Name: "workspace",
-			}})
-			tableWriter.SetColumnConfigs(cliui.FilterTableColumns(header, columns))
-
 			now := time.Now()
-			for _, workspace := range workspaces {
-				status := ""
-				inProgress := false
-				if workspace.LatestBuild.Job.Status == codersdk.ProvisionerJobRunning ||
-					workspace.LatestBuild.Job.Status == codersdk.ProvisionerJobCanceling {
-					inProgress = true
-				}
-
-				switch workspace.LatestBuild.Transition {
-				case codersdk.WorkspaceTransitionStart:
-					status = "Running"
-					if inProgress {
-						status = "Starting"
-					}
-				case codersdk.WorkspaceTransitionStop:
-					status = "Stopped"
-					if inProgress {
-						status = "Stopping"
-					}
-				case codersdk.WorkspaceTransitionDelete:
-					status = "Deleted"
-					if inProgress {
-						status = "Deleting"
-					}
-				}
-				if workspace.LatestBuild.Job.Status == codersdk.ProvisionerJobFailed {
-					status = "Failed"
-				}
-
-				lastBuilt := time.Now().UTC().Sub(workspace.LatestBuild.Job.CreatedAt).Truncate(time.Second)
-				autostartDisplay := "-"
-				if !ptr.NilOrEmpty(workspace.AutostartSchedule) {
-					if sched, err := schedule.Weekly(*workspace.AutostartSchedule); err == nil {
-						autostartDisplay = fmt.Sprintf("%s %s (%s)", sched.Time(), sched.DaysOfWeek(), sched.Location())
-					}
-				}
-
-				autostopDisplay := "-"
-				if !ptr.NilOrZero(workspace.TTLMillis) {
-					dur := time.Duration(*workspace.TTLMillis) * time.Millisecond
-					autostopDisplay = durationDisplay(dur)
-					if !workspace.LatestBuild.Deadline.IsZero() && workspace.LatestBuild.Deadline.After(now) && status == "Running" {
-						remaining := time.Until(workspace.LatestBuild.Deadline)
-						autostopDisplay = fmt.Sprintf("%s (%s)", autostopDisplay, relative(remaining))
-					}
-				}
-
-				user := usersByID[workspace.OwnerID]
-				tableWriter.AppendRow(table.Row{
-					user.Username + "/" + workspace.Name,
-					workspace.TemplateName,
-					status,
-					durationDisplay(lastBuilt),
-					workspace.Outdated,
-					autostartDisplay,
-					autostopDisplay,
-				})
+			displayWorkspaces := make([]workspaceListRow, len(workspaces))
+			for i, workspace := range workspaces {
+				displayWorkspaces[i] = workspaceListRowFromWorkspace(now, usersByID, workspace)
 			}
-			_, err = fmt.Fprintln(cmd.OutOrStdout(), tableWriter.Render())
+
+			out, err := cliui.DisplayTable(displayWorkspaces, "workspace", columns)
+			if err != nil {
+				return err
+			}
+
+			_, err = fmt.Fprintln(cmd.OutOrStdout(), out)
 			return err
 		},
 	}
 	cmd.Flags().StringArrayVarP(&columns, "column", "c", nil,
 		"Specify a column to filter in the table.")
+	cmd.Flags().StringVar(&searchQuery, "search", "", "Search for a workspace with a query.")
+	cmd.Flags().BoolVar(&me, "me", false, "Only show workspaces owned by the current user.")
 	return cmd
 }
@@ -3,21 +3,19 @@ package cli_test
 import (
 	"context"
 	"testing"
-	"time"

 	"github.com/stretchr/testify/assert"

 	"github.com/coder/coder/cli/clitest"
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 func TestList(t *testing.T) {
 	t.Parallel()
 	t.Run("Single", func(t *testing.T) {
 		t.Parallel()
-		ctx, cancelFunc := context.WithTimeout(context.Background(), 5*time.Second)
-		defer cancelFunc()
 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
 		user := coderdtest.CreateFirstUser(t, client)
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
@@ -30,6 +28,9 @@ func TestList(t *testing.T) {
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
 		cmd.SetOut(pty.Output())
+
+		ctx, cancelFunc := context.WithTimeout(context.Background(), testutil.WaitLong)
+		defer cancelFunc()
 		done := make(chan any)
 		go func() {
 			errC := cmd.ExecuteContext(ctx)
@@ -37,7 +38,7 @@ func TestList(t *testing.T) {
 			close(done)
 		}()
 		pty.ExpectMatch(workspace.Name)
-		pty.ExpectMatch("Running")
+		pty.ExpectMatch("Started")
 		cancelFunc()
 		<-done
 	})
@@ -67,6 +67,17 @@ func login() *cobra.Command {
 			}

 			client := codersdk.New(serverURL)
+
+			// Try to check the version of the server prior to logging in.
+			// It may be useful to warn the user if they are trying to login
+			// on a very old client.
+			err = checkVersions(cmd, client)
+			if err != nil {
+				// Checking versions isn't a fatal error so we print a warning
+				// and proceed.
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), cliui.Styles.Warn.Render(err.Error()))
+			}
+
 			hasInitialUser, err := client.HasFirstUser(cmd.Context())
 			if err != nil {
 				return xerrors.Errorf("has initial user: %w", err)
@@ -80,7 +91,7 @@ func login() *cobra.Command {
 					}
 					_, err := cliui.Prompt(cmd, cliui.PromptOptions{
 						Text:      "Would you like to create the first user?",
-						Default:   "yes",
+						Default:   cliui.ConfirmYes,
 						IsConfirm: true,
 					})
 					if errors.Is(err, cliui.Canceled) {
@@ -122,26 +133,29 @@ func login() *cobra.Command {
 				}

 				if password == "" {
-					password, err = cliui.Prompt(cmd, cliui.PromptOptions{
-						Text:     "Enter a " + cliui.Styles.Field.Render("password") + ":",
-						Secret:   true,
-						Validate: cliui.ValidateNotEmpty,
-					})
-					if err != nil {
-						return xerrors.Errorf("specify password prompt: %w", err)
-					}
-					_, err = cliui.Prompt(cmd, cliui.PromptOptions{
-						Text:   "Confirm " + cliui.Styles.Field.Render("password") + ":",
-						Secret: true,
-						Validate: func(s string) error {
-							if s != password {
-								return xerrors.Errorf("Passwords do not match")
-							}
-							return nil
-						},
-					})
-					if err != nil {
-						return xerrors.Errorf("confirm password prompt: %w", err)
+					var matching bool
+
+					for !matching {
+						password, err = cliui.Prompt(cmd, cliui.PromptOptions{
+							Text:     "Enter a " + cliui.Styles.Field.Render("password") + ":",
+							Secret:   true,
+							Validate: cliui.ValidateNotEmpty,
+						})
+						if err != nil {
+							return xerrors.Errorf("specify password prompt: %w", err)
+						}
+						confirm, err := cliui.Prompt(cmd, cliui.PromptOptions{
+							Text:   "Confirm " + cliui.Styles.Field.Render("password") + ":",
+							Secret: true,
+						})
+						if err != nil {
+							return xerrors.Errorf("confirm password prompt: %w", err)
+						}
+
+						matching = confirm == password
+						if !matching {
+							_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Error.Render("Passwords do not match"))
+						}
 					}
 				}

@@ -8,6 +8,7 @@ import (
 	"github.com/stretchr/testify/require"

 	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/pty/ptytest"
 )
@@ -92,7 +93,7 @@ func TestLogin(t *testing.T) {
 		go func() {
 			defer close(doneChan)
 			err := root.ExecuteContext(ctx)
-			assert.ErrorIs(t, err, context.Canceled)
+			assert.NoError(t, err)
 		}()

 		matches := []string{
@@ -108,9 +109,15 @@ func TestLogin(t *testing.T) {
 			pty.ExpectMatch(match)
 			pty.WriteLine(value)
 		}
+
+		// Validate that we reprompt for matching passwords.
 		pty.ExpectMatch("Passwords do not match")
-		pty.ExpectMatch("password") // Re-prompt password.
-		cancel()
+		pty.ExpectMatch("Enter a " + cliui.Styles.Field.Render("password"))
+
+		pty.WriteLine("pass")
+		pty.ExpectMatch("Confirm")
+		pty.WriteLine("pass")
+		pty.ExpectMatch("Welcome to Coder")
 		<-doneChan
 	})

@@ -16,7 +16,7 @@ func logout() *cobra.Command {
 		Use:   "logout",
 		Short: "Remove the local authenticated session",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -26,9 +26,9 @@ func logout() *cobra.Command {
 			config := createConfig(cmd)

 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
-				Text:      "Are you sure you want to logout?",
+				Text:      "Are you sure you want to log out?",
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
@@ -41,7 +41,7 @@ func TestLogout(t *testing.T) {
 			assert.NoFileExists(t, string(config.Session()))
 		}()

-		pty.ExpectMatch("Are you sure you want to logout?")
+		pty.ExpectMatch("Are you sure you want to log out?")
 		pty.WriteLine("yes")
 		pty.ExpectMatch("You are no longer logged in. You can log in using 'coder login <url>'.")
 		<-logoutChan
@@ -152,19 +152,19 @@ func TestLogout(t *testing.T) {
 			err = os.Chmod(string(config), 0500)
 			require.NoError(t, err)
 		}
-		t.Cleanup(func() {
+		defer func() {
 			if runtime.GOOS == "windows" {
 				// Closing the opened files for cleanup.
 				err = urlFile.Close()
-				require.NoError(t, err)
+				assert.NoError(t, err)
 				err = sessionFile.Close()
-				require.NoError(t, err)
+				assert.NoError(t, err)
 			} else {
 				// Setting the permissions back for cleanup.
-				err = os.Chmod(string(config), 0700)
-				require.NoError(t, err)
+				err = os.Chmod(string(config), 0o700)
+				assert.NoError(t, err)
 			}
-		})
+		}()

 		logoutChan := make(chan struct{})
 		logout, _ := clitest.New(t, "logout", "--global-config", string(config))
@@ -186,7 +186,7 @@ func TestLogout(t *testing.T) {
 			assert.Regexp(t, errRegex, err.Error())
 		}()

-		pty.ExpectMatch("Are you sure you want to logout?")
+		pty.ExpectMatch("Are you sure you want to log out?")
 		pty.WriteLine("yes")
 		<-logoutChan
 	})
@@ -1,18 +1,18 @@
 package cli

 import (
-	"github.com/jedib0t/go-pretty/v6/table"
 	"github.com/spf13/cobra"
-
-	"github.com/coder/coder/cli/cliui"
-	"github.com/coder/coder/codersdk"
 )

 func parameters() *cobra.Command {
 	cmd := &cobra.Command{
-		Short:   "List parameters for a given scope",
-		Example: "coder parameters list workspace my-workspace",
-		Use:     "parameters",
+		Short: "List parameters for a given scope",
+		Example: formatExamples(
+			example{
+				Command: "coder parameters list workspace my-workspace",
+			},
+		),
+		Use: "parameters",
 		// Currently hidden as this shows parameter values, not parameter
 		// schemes. Until we have a good way to distinguish the two, it's better
 		// not to add confusion or lock ourselves into a certain api.
@@ -26,29 +26,3 @@ func parameters() *cobra.Command {
 	)
 	return cmd
 }
-
-// displayParameters will return a table displaying all parameters passed in.
-// filterColumns must be a subset of the parameter fields and will determine which
-// columns to display
-func displayParameters(filterColumns []string, params ...codersdk.Parameter) string {
-	tableWriter := cliui.Table()
-	header := table.Row{"id", "scope", "scope id", "name", "source scheme", "destination scheme", "created at", "updated at"}
-	tableWriter.AppendHeader(header)
-	tableWriter.SetColumnConfigs(cliui.FilterTableColumns(header, filterColumns))
-	tableWriter.SortBy([]table.SortBy{{
-		Name: "name",
-	}})
-	for _, param := range params {
-		tableWriter.AppendRow(table.Row{
-			param.ID.String(),
-			param.Scope,
-			param.ScopeID.String(),
-			param.Name,
-			param.SourceScheme,
-			param.DestinationScheme,
-			param.CreatedAt,
-			param.UpdatedAt,
-		})
-	}
-	return tableWriter.Render()
-}
@@ -7,6 +7,7 @@ import (
 	"github.com/spf13/cobra"
 	"golang.org/x/xerrors"

+	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/codersdk"
 )

@@ -21,7 +22,7 @@ func parameterList() *cobra.Command {
 		RunE: func(cmd *cobra.Command, args []string) error {
 			scope, name := args[0], args[1]

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -70,11 +71,16 @@ func parameterList() *cobra.Command {
 				return xerrors.Errorf("fetch params: %w", err)
 			}

-			_, err = fmt.Fprintln(cmd.OutOrStdout(), displayParameters(columns, params...))
+			out, err := cliui.DisplayTable(params, "name", columns)
+			if err != nil {
+				return xerrors.Errorf("render table: %w", err)
+			}
+
+			_, err = fmt.Fprintln(cmd.OutOrStdout(), out)
 			return err
 		},
 	}
-	cmd.Flags().StringArrayVarP(&columns, "column", "c", []string{"name", "source_scheme", "destination_scheme"},
+	cmd.Flags().StringArrayVarP(&columns, "column", "c", []string{"name", "scope", "destination scheme"},
 		"Specify a column to filter in the table.")
 	return cmd
 }
@@ -29,31 +29,35 @@ func portForward() *cobra.Command {
 	)
 	cmd := &cobra.Command{
 		Use:     "port-forward <workspace>",
+		Short:   "Forward one or more ports from the local machine to the remote workspace",
 		Aliases: []string{"tunnel"},
 		Args:    cobra.ExactArgs(1),
-		Example: `
-  - Port forward a single TCP port from 1234 in the workspace to port 5678 on
-    your local machine
-
-    ` + cliui.Styles.Code.Render("$ coder port-forward <workspace> --tcp 5678:1234") + `
-
-  - Port forward a single UDP port from port 9000 to port 9000 on your local
-    machine
-
-    ` + cliui.Styles.Code.Render("$ coder port-forward <workspace> --udp 9000") + `
-
-  - Forward a Unix socket in the workspace to a local Unix socket
-
-    ` + cliui.Styles.Code.Render("$ coder port-forward <workspace> --unix ./local.sock:~/remote.sock") + `
-
-  - Forward a Unix socket in the workspace to a local TCP port
-
-    ` + cliui.Styles.Code.Render("$ coder port-forward <workspace> --unix 8080:~/remote.sock") + `
-
-  - Port forward multiple TCP ports and a UDP port
-
-    ` + cliui.Styles.Code.Render("$ coder port-forward <workspace> --tcp 8080:8080 --tcp 9000:3000 --udp 5353:53"),
+		Example: formatExamples(
+			example{
+				Description: "Port forward a single TCP port from 1234 in the workspace to port 5678 on your local machine",
+				Command:     "coder port-forward <workspace> --tcp 5678:1234",
+			},
+			example{
+				Description: "Port forward a single UDP port from port 9000 to port 9000 on your local machine",
+				Command:     "coder port-forward <workspace> --udp 9000",
+			},
+			example{
+				Description: "Forward a Unix socket in the workspace to a local Unix socket",
+				Command:     "coder port-forward <workspace> --unix ./local.sock:~/remote.sock",
+			},
+			example{
+				Description: "Forward a Unix socket in the workspace to a local TCP port",
+				Command:     "coder port-forward <workspace> --unix 8080:~/remote.sock",
+			},
+			example{
+				Description: "Port forward multiple TCP ports and a UDP port",
+				Command:     "coder port-forward <workspace> --tcp 8080:8080 --tcp 9000:3000 --udp 5353:53",
+			},
+		),
 		RunE: func(cmd *cobra.Command, args []string) error {
+			ctx, cancel := context.WithCancel(cmd.Context())
+			defer cancel()
+
 			specs, err := parsePortForwards(tcpForwards, udpForwards, unixForwards)
 			if err != nil {
 				return xerrors.Errorf("parse port-forward specs: %w", err)
@@ -66,12 +70,12 @@ func portForward() *cobra.Command {
 				return xerrors.New("no port-forwards requested")
 			}

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}

-			workspace, agent, err := getWorkspaceAndAgent(cmd, client, codersdk.Me, args[0], false)
+			workspace, agent, err := getWorkspaceAndAgent(ctx, cmd, client, codersdk.Me, args[0], false)
 			if err != nil {
 				return err
 			}
@@ -79,13 +83,13 @@ func portForward() *cobra.Command {
 				return xerrors.New("workspace must be in start transition to port-forward")
 			}
 			if workspace.LatestBuild.Job.CompletedAt == nil {
-				err = cliui.WorkspaceBuild(cmd.Context(), cmd.ErrOrStderr(), client, workspace.LatestBuild.ID, workspace.CreatedAt)
+				err = cliui.WorkspaceBuild(ctx, cmd.ErrOrStderr(), client, workspace.LatestBuild.ID, workspace.CreatedAt)
 				if err != nil {
 					return err
 				}
 			}

-			err = cliui.Agent(cmd.Context(), cmd.ErrOrStderr(), cliui.AgentOptions{
+			err = cliui.Agent(ctx, cmd.ErrOrStderr(), cliui.AgentOptions{
 				WorkspaceName: workspace.Name,
 				Fetch: func(ctx context.Context) (codersdk.WorkspaceAgent, error) {
 					return client.WorkspaceAgent(ctx, agent.ID)
@@ -95,7 +99,7 @@ func portForward() *cobra.Command {
 				return xerrors.Errorf("await agent: %w", err)
 			}

-			conn, err := client.DialWorkspaceAgent(cmd.Context(), agent.ID, nil)
+			conn, err := client.DialWorkspaceAgent(ctx, agent.ID, nil)
 			if err != nil {
 				return xerrors.Errorf("dial workspace agent: %w", err)
 			}
@@ -103,7 +107,6 @@ func portForward() *cobra.Command {

 			// Start all listeners.
 			var (
-				ctx, cancel       = context.WithCancel(cmd.Context())
 				wg                = new(sync.WaitGroup)
 				listeners         = make([]net.Listener, len(specs))
 				closeAllListeners = func() {
@@ -115,11 +118,11 @@ func portForward() *cobra.Command {
 					}
 				}
 			)
-			defer cancel()
+			defer closeAllListeners()
+
 			for i, spec := range specs {
 				l, err := listenAndPortForward(ctx, cmd, conn, wg, spec)
 				if err != nil {
-					closeAllListeners()
 					return err
 				}
 				listeners[i] = l
@@ -128,7 +131,10 @@ func portForward() *cobra.Command {
 			// Wait for the context to be canceled or for a signal and close
 			// all listeners.
 			var closeErr error
+			wg.Add(1)
 			go func() {
+				defer wg.Done()
+
 				sigs := make(chan os.Signal, 1)
 				signal.Notify(sigs, syscall.SIGINT, syscall.SIGTERM)

@@ -6,7 +6,6 @@ import (
 	"fmt"
 	"io"
 	"net"
-	"os"
 	"path/filepath"
 	"runtime"
 	"strings"
@@ -24,6 +23,7 @@ import (
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
+	"github.com/coder/coder/testutil"
 )

 func TestPortForward(t *testing.T) {
@@ -119,44 +119,35 @@ func TestPortForward(t *testing.T) {
 					t.Skip("Unix socket forwarding isn't supported on Windows")
 				}

-				tmpDir, err := os.MkdirTemp("", "coderd_agent_test_")
-				require.NoError(t, err, "create temp dir for unix listener")
-				t.Cleanup(func() {
-					_ = os.RemoveAll(tmpDir)
-				})
-
+				tmpDir := t.TempDir()
 				l, err := net.Listen("unix", filepath.Join(tmpDir, "test.sock"))
 				require.NoError(t, err, "create UDP listener")
 				return l
 			},
 			setupLocal: func(t *testing.T) (string, string) {
-				tmpDir, err := os.MkdirTemp("", "coderd_agent_test_")
-				require.NoError(t, err, "create temp dir for unix listener")
-				t.Cleanup(func() {
-					_ = os.RemoveAll(tmpDir)
-				})
-
+				tmpDir := t.TempDir()
 				path := filepath.Join(tmpDir, "test.sock")
 				return path, path
 			},
 		},
 	}

+	// Setup agent once to be shared between test-cases (avoid expensive
+	// non-parallel setup).
+	var (
+		client       = coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user         = coderdtest.CreateFirstUser(t, client)
+		_, workspace = runAgent(t, client, user.UserID)
+	)
+
 	for _, c := range cases { //nolint:paralleltest // the `c := c` confuses the linter
 		c := c
-		// Avoid parallel test here because setupLocal reserves
+		// Delay parallel tests here because setupLocal reserves
 		// a free open port which is not guaranteed to be free
-		// after the listener closes.
-		//nolint:paralleltest
+		// between the listener closing and port-forward ready.
 		t.Run(c.name, func(t *testing.T) {
-			//nolint:paralleltest
 			t.Run("OnePort", func(t *testing.T) {
-				var (
-					client       = coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
-					user         = coderdtest.CreateFirstUser(t, client)
-					_, workspace = runAgent(t, client, user.UserID)
-					p1           = setupTestListener(t, c.setupRemote(t))
-				)
+				p1 := setupTestListener(t, c.setupRemote(t))

 				// Create a flag that forwards from local to listener 1.
 				localAddress, localFlag := c.setupLocal(t)
@@ -167,7 +158,7 @@ func TestPortForward(t *testing.T) {
 				cmd, root := clitest.New(t, "port-forward", workspace.Name, flag)
 				clitest.SetupConfig(t, client, root)
 				buf := newThreadSafeBuffer()
-				cmd.SetOut(io.MultiWriter(buf, os.Stderr))
+				cmd.SetOut(buf)
 				ctx, cancel := context.WithCancel(context.Background())
 				defer cancel()
 				errC := make(chan error)
@@ -176,9 +167,11 @@ func TestPortForward(t *testing.T) {
 				}()
 				waitForPortForwardReady(t, buf)

+				t.Parallel() // Port is reserved, enable parallel execution.
+
 				// Open two connections simultaneously and test them out of
 				// sync.
-				d := net.Dialer{Timeout: 3 * time.Second}
+				d := net.Dialer{Timeout: testutil.WaitShort}
 				c1, err := d.DialContext(ctx, c.network, localAddress)
 				require.NoError(t, err, "open connection 1 to 'local' listener")
 				defer c1.Close()
@@ -196,11 +189,8 @@ func TestPortForward(t *testing.T) {
 			//nolint:paralleltest
 			t.Run("TwoPorts", func(t *testing.T) {
 				var (
-					client       = coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
-					user         = coderdtest.CreateFirstUser(t, client)
-					_, workspace = runAgent(t, client, user.UserID)
-					p1           = setupTestListener(t, c.setupRemote(t))
-					p2           = setupTestListener(t, c.setupRemote(t))
+					p1 = setupTestListener(t, c.setupRemote(t))
+					p2 = setupTestListener(t, c.setupRemote(t))
 				)

 				// Create a flags for listener 1 and listener 2.
@@ -214,7 +204,7 @@ func TestPortForward(t *testing.T) {
 				cmd, root := clitest.New(t, "port-forward", workspace.Name, flag1, flag2)
 				clitest.SetupConfig(t, client, root)
 				buf := newThreadSafeBuffer()
-				cmd.SetOut(io.MultiWriter(buf, os.Stderr))
+				cmd.SetOut(buf)
 				ctx, cancel := context.WithCancel(context.Background())
 				defer cancel()
 				errC := make(chan error)
@@ -223,9 +213,11 @@ func TestPortForward(t *testing.T) {
 				}()
 				waitForPortForwardReady(t, buf)

+				t.Parallel() // Port is reserved, enable parallel execution.
+
 				// Open a connection to both listener 1 and 2 simultaneously and
 				// then test them out of order.
-				d := net.Dialer{Timeout: 3 * time.Second}
+				d := net.Dialer{Timeout: testutil.WaitShort}
 				c1, err := d.DialContext(ctx, c.network, localAddress1)
 				require.NoError(t, err, "open connection 1 to 'local' listener 1")
 				defer c1.Close()
@@ -246,10 +238,6 @@ func TestPortForward(t *testing.T) {
 	//nolint:paralleltest
 	t.Run("TCP2Unix", func(t *testing.T) {
 		var (
-			client       = coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
-			user         = coderdtest.CreateFirstUser(t, client)
-			_, workspace = runAgent(t, client, user.UserID)
-
 			// Find the TCP and Unix cases so we can use their setupLocal and
 			// setupRemote methods respectively.
 			tcpCase  = cases[0]
@@ -269,7 +257,7 @@ func TestPortForward(t *testing.T) {
 		cmd, root := clitest.New(t, "port-forward", workspace.Name, flag)
 		clitest.SetupConfig(t, client, root)
 		buf := newThreadSafeBuffer()
-		cmd.SetOut(io.MultiWriter(buf, os.Stderr))
+		cmd.SetOut(buf)
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 		errC := make(chan error)
@@ -278,9 +266,11 @@ func TestPortForward(t *testing.T) {
 		}()
 		waitForPortForwardReady(t, buf)

+		t.Parallel() // Port is reserved, enable parallel execution.
+
 		// Open two connections simultaneously and test them out of
 		// sync.
-		d := net.Dialer{Timeout: 3 * time.Second}
+		d := net.Dialer{Timeout: testutil.WaitShort}
 		c1, err := d.DialContext(ctx, tcpCase.network, localAddress)
 		require.NoError(t, err, "open connection 1 to 'local' listener")
 		defer c1.Close()
@@ -299,9 +289,6 @@ func TestPortForward(t *testing.T) {
 	//nolint:paralleltest
 	t.Run("All", func(t *testing.T) {
 		var (
-			client       = coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
-			user         = coderdtest.CreateFirstUser(t, client)
-			_, workspace = runAgent(t, client, user.UserID)
 			// These aren't fixed size because we exclude Unix on Windows.
 			dials = []addr{}
 			flags = []string{}
@@ -330,7 +317,7 @@ func TestPortForward(t *testing.T) {
 		cmd, root := clitest.New(t, append([]string{"port-forward", workspace.Name}, flags...)...)
 		clitest.SetupConfig(t, client, root)
 		buf := newThreadSafeBuffer()
-		cmd.SetOut(io.MultiWriter(buf, os.Stderr))
+		cmd.SetOut(buf)
 		ctx, cancel := context.WithCancel(context.Background())
 		defer cancel()
 		errC := make(chan error)
@@ -339,9 +326,11 @@ func TestPortForward(t *testing.T) {
 		}()
 		waitForPortForwardReady(t, buf)

+		t.Parallel() // Port is reserved, enable parallel execution.
+
 		// Open connections to all items in the "dial" array.
 		var (
-			d     = net.Dialer{Timeout: 3 * time.Second}
+			d     = net.Dialer{Timeout: testutil.WaitShort}
 			conns = make([]net.Conn, len(dials))
 		)
 		for i, a := range dials {
@@ -402,7 +391,7 @@ func runAgent(t *testing.T, client *codersdk.Client, userID uuid.UUID) ([]coders
 	coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

 	// Start workspace agent in a goroutine
-	cmd, root := clitest.New(t, "agent", "--agent-token", agentToken, "--agent-url", client.URL.String())
+	cmd, root := clitest.New(t, "agent", "--agent-token", agentToken, "--agent-url", client.URL.String(), "--wireguard=false")
 	clitest.SetupConfig(t, client, root)
 	errC := make(chan error)
 	agentCtx, agentCancel := context.WithCancel(ctx)
@@ -425,6 +414,8 @@ func runAgent(t *testing.T, client *codersdk.Client, userID uuid.UUID) ([]coders
 // setupTestListener starts accepting connections and echoing a single packet.
 // Returns the listener and the listen port or Unix path.
 func setupTestListener(t *testing.T, l net.Listener) string {
+	t.Helper()
+
 	// Wait for listener to completely exit before releasing.
 	done := make(chan struct{})
 	t.Cleanup(func() {
@@ -440,6 +431,7 @@ func setupTestListener(t *testing.T, l net.Listener) string {
 		for {
 			c, err := l.Accept()
 			if err != nil {
+				_ = l.Close()
 				return
 			}

@@ -479,6 +471,7 @@ func testAccept(t *testing.T, c net.Conn) {
 }

 func assertReadPayload(t *testing.T, r io.Reader, payload []byte) {
+	t.Helper()
 	b := make([]byte, len(payload)+16)
 	n, err := r.Read(b)
 	assert.NoError(t, err, "read payload")
@@ -487,14 +480,16 @@ func assertReadPayload(t *testing.T, r io.Reader, payload []byte) {
 }

 func assertWritePayload(t *testing.T, w io.Writer, payload []byte) {
+	t.Helper()
 	n, err := w.Write(payload)
 	assert.NoError(t, err, "write payload")
 	assert.Equal(t, len(payload), n, "payload length does not match")
 }

 func waitForPortForwardReady(t *testing.T, output *threadSafeBuffer) {
+	t.Helper()
 	for i := 0; i < 100; i++ {
-		time.Sleep(250 * time.Millisecond)
+		time.Sleep(testutil.IntervalMedium)

 		data := output.String()
 		if strings.Contains(data, "Ready!") {
@@ -20,7 +20,7 @@ func publickey() *cobra.Command {
 		Aliases: []string{"pubkey"},
 		Short:   "Output your public key for Git operations",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return xerrors.Errorf("create codersdk client: %w", err)
 			}
@@ -13,6 +13,7 @@ import (
 func TestPublicKey(t *testing.T) {
 	t.Parallel()
 	t.Run("OK", func(t *testing.T) {
+		t.Parallel()
 		client := coderdtest.New(t, nil)
 		_ = coderdtest.CreateFirstUser(t, client)
 		cmd, root := clitest.New(t, "publickey")
@@ -0,0 +1,62 @@
+package cli
+
+import (
+	"fmt"
+
+	"github.com/spf13/cobra"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/cli/cliui"
+	"github.com/coder/coder/codersdk"
+)
+
+func rename() *cobra.Command {
+	cmd := &cobra.Command{
+		Annotations: workspaceCommand,
+		Use:         "rename <workspace> <new name>",
+		Short:       "Rename a workspace",
+		Args:        cobra.ExactArgs(2),
+		// Keep hidden until renaming is safe, see:
+		// * https://github.com/coder/coder/issues/3000
+		// * https://github.com/coder/coder/issues/3386
+		Hidden: true,
+		RunE: func(cmd *cobra.Command, args []string) error {
+			client, err := CreateClient(cmd)
+			if err != nil {
+				return err
+			}
+			workspace, err := namedWorkspace(cmd, client, args[0])
+			if err != nil {
+				return xerrors.Errorf("get workspace: %w", err)
+			}
+
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "%s\n\n",
+				cliui.Styles.Wrap.Render("WARNING: A rename can result in data loss if a resource references the workspace name in the template (e.g volumes)."),
+			)
+			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
+				Text: fmt.Sprintf("Type %q to confirm rename:", workspace.Name),
+				Validate: func(s string) error {
+					if s == workspace.Name {
+						return nil
+					}
+					return xerrors.Errorf("Input %q does not match %q", s, workspace.Name)
+				},
+			})
+			if err != nil {
+				return err
+			}
+
+			err = client.UpdateWorkspace(cmd.Context(), workspace.ID, codersdk.UpdateWorkspaceRequest{
+				Name: args[1],
+			})
+			if err != nil {
+				return xerrors.Errorf("rename workspace: %w", err)
+			}
+			return nil
+		},
+	}
+
+	cliui.AllowSkipPrompt(cmd)
+
+	return cmd
+}
@@ -0,0 +1,52 @@
+package cli_test
+
+import (
+	"context"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
+)
+
+func TestRename(t *testing.T) {
+	t.Parallel()
+
+	client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+	user := coderdtest.CreateFirstUser(t, client)
+	version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+	coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+	template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+	workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+	coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
+
+	ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+	defer cancel()
+
+	want := workspace.Name + "-test"
+	cmd, root := clitest.New(t, "rename", workspace.Name, want, "--yes")
+	clitest.SetupConfig(t, client, root)
+	pty := ptytest.New(t)
+	cmd.SetIn(pty.Input())
+	cmd.SetOut(pty.Output())
+
+	errC := make(chan error, 1)
+	go func() {
+		errC <- cmd.ExecuteContext(ctx)
+	}()
+
+	pty.ExpectMatch("confirm rename:")
+	pty.WriteLine(workspace.Name)
+
+	require.NoError(t, <-errC)
+
+	ws, err := client.Workspace(ctx, workspace.ID)
+	assert.NoError(t, err)
+
+	got := ws.Name
+	assert.Equal(t, want, got, "workspace name did not change")
+}
@@ -2,6 +2,7 @@ package cli

 import (
 	"database/sql"
+	"fmt"

 	"github.com/spf13/cobra"
 	"golang.org/x/xerrors"
@@ -80,6 +81,7 @@ func resetPassword() *cobra.Command {
 				return xerrors.Errorf("updating password: %w", err)
 			}

+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nPassword has been reset for user %s!\n", cliui.Styles.Keyword.Render(user.Username))
 			return nil
 		},
 	}
@@ -5,7 +5,6 @@ import (
 	"net/url"
 	"runtime"
 	"testing"
-	"time"

 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -14,6 +13,7 @@ import (
 	"github.com/coder/coder/coderd/database/postgres"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 // nolint:paralleltest
@@ -38,23 +38,26 @@ func TestResetPassword(t *testing.T) {
 	defer closeFunc()
 	ctx, cancelFunc := context.WithCancel(context.Background())
 	serverDone := make(chan struct{})
-	serverCmd, cfg := clitest.New(t, "server", "--address", ":0", "--postgres-url", connectionURL)
+	serverCmd, cfg := clitest.New(t,
+		"server",
+		"--address", ":0",
+		"--postgres-url", connectionURL,
+		"--cache-dir", t.TempDir(),
+	)
 	go func() {
 		defer close(serverDone)
 		err = serverCmd.ExecuteContext(ctx)
 		assert.ErrorIs(t, err, context.Canceled)
 	}()
-	var client *codersdk.Client
+	var rawURL string
 	require.Eventually(t, func() bool {
-		rawURL, err := cfg.URL().Read()
-		if err != nil {
-			return false
-		}
-		accessURL, err := url.Parse(rawURL)
-		require.NoError(t, err)
-		client = codersdk.New(accessURL)
-		return true
-	}, 15*time.Second, 25*time.Millisecond)
+		rawURL, err = cfg.URL().Read()
+		return err == nil && rawURL != ""
+	}, testutil.WaitLong, testutil.IntervalFast)
+	accessURL, err := url.Parse(rawURL)
+	require.NoError(t, err)
+	client := codersdk.New(accessURL)
+
 	_, err = client.CreateFirstUser(ctx, codersdk.CreateFirstUserRequest{
 		Email:            email,
 		Username:         username,
@@ -1,14 +1,17 @@
 package cli

 import (
+	"flag"
 	"fmt"
 	"net/url"
 	"os"
 	"strings"
+	"text/template"
 	"time"

 	"golang.org/x/xerrors"

+	"github.com/charmbracelet/lipgloss"
 	"github.com/kirsle/configdir"
 	"github.com/mattn/go-isatty"
 	"github.com/spf13/cobra"
@@ -17,6 +20,7 @@ import (
 	"github.com/coder/coder/cli/cliflag"
 	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/cli/config"
+	"github.com/coder/coder/coderd"
 	"github.com/coder/coder/codersdk"
 )

@@ -26,7 +30,7 @@ var (
 	// Applied as annotations to workspace commands
 	// so they display in a separated "help" section.
 	workspaceCommand = map[string]string{
-		"workspaces": " ",
+		"workspaces": "",
 	}
 )

@@ -37,64 +41,118 @@ const (
 	varAgentURL        = "agent-url"
 	varGlobalConfig    = "global-config"
 	varNoOpen          = "no-open"
+	varNoVersionCheck  = "no-version-warning"
 	varForceTty        = "force-tty"
+	varVerbose         = "verbose"
 	notLoggedInMessage = "You are not logged in. Try logging in using 'coder login <url>'."
+
+	envNoVersionCheck = "CODER_NO_VERSION_WARNING"
+)
+
+var (
+	errUnauthenticated = xerrors.New(notLoggedInMessage)
+	envSessionToken    = "CODER_SESSION_TOKEN"
 )

 func init() {
-	// Customizes the color of headings to make subcommands more visually
-	// appealing.
-	header := cliui.Styles.Placeholder
-	cobra.AddTemplateFunc("usageHeader", func(s string) string {
-		return header.Render(s)
-	})
+	// Set cobra template functions in init to avoid conflicts in tests.
+	cobra.AddTemplateFuncs(templateFunctions)
 }

-func Root() *cobra.Command {
+func Core() []*cobra.Command {
+	return []*cobra.Command{
+		configSSH(),
+		create(),
+		deleteWorkspace(),
+		dotfiles(),
+		gitssh(),
+		list(),
+		login(),
+		logout(),
+		parameters(),
+		portForward(),
+		publickey(),
+		resetPassword(),
+		schedules(),
+		show(),
+		ssh(),
+		start(),
+		state(),
+		stop(),
+		rename(),
+		templates(),
+		update(),
+		users(),
+		versionCmd(),
+		wireguardPortForward(),
+		workspaceAgent(),
+		features(),
+	}
+}
+
+func AGPL() []*cobra.Command {
+	all := append(Core(), Server(coderd.New))
+	return all
+}
+
+func Root(subcommands []*cobra.Command) *cobra.Command {
 	cmd := &cobra.Command{
 		Use:           "coder",
 		SilenceErrors: true,
 		SilenceUsage:  true,
 		Long: `Coder — A tool for provisioning self-hosted development environments.
 `,
-		Example: `  Start a Coder server.
-  ` + cliui.Styles.Code.Render("$ coder server") + `
+		PersistentPreRun: func(cmd *cobra.Command, args []string) {
+			err := func() error {
+				if cliflag.IsSetBool(cmd, varNoVersionCheck) {
+					return nil
+				}

-  Get started by creating a template from an example.
-  ` + cliui.Styles.Code.Render("$ coder templates init"),
+				// Login handles checking the versions itself since it
+				// has a handle to an unauthenticated client.
+				// Server is skipped for obvious reasons.
+				if cmd.Name() == "login" || cmd.Name() == "server" || cmd.Name() == "gitssh" {
+					return nil
+				}
+
+				client, err := CreateClient(cmd)
+				// If the client is unauthenticated we can ignore the check.
+				// The child commands should handle an unauthenticated client.
+				if xerrors.Is(err, errUnauthenticated) {
+					return nil
+				}
+				if err != nil {
+					return xerrors.Errorf("create client: %w", err)
+				}
+				return checkVersions(cmd, client)
+			}()
+			if err != nil {
+				// Just log the error here. We never want to fail a command
+				// due to a pre-run.
+				_, _ = fmt.Fprintf(cmd.ErrOrStderr(),
+					cliui.Styles.Warn.Render("check versions error: %s"), err)
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr())
+			}
+		},
+		Example: formatExamples(
+			example{
+				Description: "Start a Coder server",
+				Command:     "coder server",
+			},
+			example{
+				Description: "Get started by creating a template from an example",
+				Command:     "coder templates init",
+			},
+		),
 	}

-	cmd.AddCommand(
-		configSSH(),
-		create(),
-		delete(),
-		dotfiles(),
-		gitssh(),
-		list(),
-		login(),
-		logout(),
-		publickey(),
-		resetPassword(),
-		schedules(),
-		server(),
-		show(),
-		start(),
-		state(),
-		stop(),
-		ssh(),
-		templates(),
-		update(),
-		users(),
-		portForward(),
-		workspaceAgent(),
-		versionCmd(),
-		parameters(),
-	)
+	cmd.AddCommand(subcommands...)

 	cmd.SetUsageTemplate(usageTemplate())

 	cmd.PersistentFlags().String(varURL, "", "Specify the URL to your deployment.")
-	cmd.PersistentFlags().String(varToken, "", "Specify an authentication token.")
+	cliflag.Bool(cmd.PersistentFlags(), varNoVersionCheck, "", envNoVersionCheck, false, "Suppress warning when client and server versions do not match.")
+	cliflag.String(cmd.PersistentFlags(), varToken, "", envSessionToken, "", fmt.Sprintf("Specify an authentication token. For security reasons setting %s is preferred.", envSessionToken))
 	cliflag.String(cmd.PersistentFlags(), varAgentToken, "", "CODER_AGENT_TOKEN", "", "Specify an agent authentication token.")
 	_ = cmd.PersistentFlags().MarkHidden(varAgentToken)
 	cliflag.String(cmd.PersistentFlags(), varAgentURL, "", "CODER_AGENT_URL", "", "Specify the URL for an agent to access your deployment.")
@@ -104,6 +162,7 @@ func Root() *cobra.Command {
 	_ = cmd.PersistentFlags().MarkHidden(varForceTty)
 	cmd.PersistentFlags().Bool(varNoOpen, false, "Block automatically opening URLs in the browser.")
 	_ = cmd.PersistentFlags().MarkHidden(varNoOpen)
+	cliflag.Bool(cmd.PersistentFlags(), varVerbose, "v", "CODER_VERBOSE", false, "Enable verbose output")

 	return cmd
 }
@@ -111,9 +170,8 @@ func Root() *cobra.Command {
 // versionCmd prints the coder version
 func versionCmd() *cobra.Command {
 	return &cobra.Command{
-		Use:     "version",
-		Short:   "Show coder version",
-		Example: "coder version",
+		Use:   "version",
+		Short: "Show coder version",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			var str strings.Builder
 			_, _ = str.WriteString(fmt.Sprintf("Coder %s", buildinfo.Version()))
@@ -129,9 +187,13 @@ func versionCmd() *cobra.Command {
 	}
 }

-// createClient returns a new client from the command context.
+func isTest() bool {
+	return flag.Lookup("test.v") != nil
+}
+
+// CreateClient returns a new client from the command context.
 // It reads from global configuration files if flags are not set.
-func createClient(cmd *cobra.Command) (*codersdk.Client, error) {
+func CreateClient(cmd *cobra.Command) (*codersdk.Client, error) {
 	root := createConfig(cmd)
 	rawURL, err := cmd.Flags().GetString(varURL)
 	if err != nil || rawURL == "" {
@@ -139,7 +201,7 @@ func createClient(cmd *cobra.Command) (*codersdk.Client, error) {
 		if err != nil {
 			// If the configuration files are absent, the user is logged out
 			if os.IsNotExist(err) {
-				return nil, xerrors.New(notLoggedInMessage)
+				return nil, errUnauthenticated
 			}
 			return nil, err
 		}
@@ -154,7 +216,7 @@ func createClient(cmd *cobra.Command) (*codersdk.Client, error) {
 		if err != nil {
 			// If the configuration files are absent, the user is logged out
 			if os.IsNotExist(err) {
-				return nil, xerrors.New(notLoggedInMessage)
+				return nil, errUnauthenticated
 			}
 			return nil, err
 		}
@@ -165,7 +227,7 @@ func createClient(cmd *cobra.Command) (*codersdk.Client, error) {
 }

 // createAgentClient returns a new client from the command context.
-// It works just like createClient, but uses the agent token and URL instead.
+// It works just like CreateClient, but uses the agent token and URL instead.
 func createAgentClient(cmd *cobra.Command) (*codersdk.Client, error) {
 	rawURL, err := cmd.Flags().GetString(varAgentURL)
 	if err != nil {
@@ -261,6 +323,30 @@ func isTTYOut(cmd *cobra.Command) bool {
 	return isatty.IsTerminal(file.Fd())
 }

+var templateFunctions = template.FuncMap{
+	"usageHeader":        usageHeader,
+	"isWorkspaceCommand": isWorkspaceCommand,
+}
+
+func usageHeader(s string) string {
+	// Customizes the color of headings to make subcommands more visually
+	// appealing.
+	return cliui.Styles.Placeholder.Render(s)
+}
+
+func isWorkspaceCommand(cmd *cobra.Command) bool {
+	if _, ok := cmd.Annotations["workspaces"]; ok {
+		return true
+	}
+	var ws bool
+	cmd.VisitParents(func(cmd *cobra.Command) {
+		if _, ok := cmd.Annotations["workspaces"]; ok {
+			ws = true
+		}
+	})
+	return ws
+}
+
 func usageTemplate() string {
 	// usageHeader is defined in init().
 	return `{{usageHeader "Usage:"}}
@@ -281,19 +367,21 @@ func usageTemplate() string {
 {{.Example}}
 {{end}}

+{{- $isRootHelp := (not .HasParent)}}
 {{- if .HasAvailableSubCommands}}
 {{usageHeader "Commands:"}}
  {{- range .Commands}}
-    {{- if (or (and .IsAvailableCommand (eq (len .Annotations) 0)) (eq .Name "help"))}}
+    {{- $isRootWorkspaceCommand := (and $isRootHelp (isWorkspaceCommand .))}}
+    {{- if (or (and .IsAvailableCommand (not $isRootWorkspaceCommand)) (eq .Name "help"))}}
  {{rpad .Name .NamePadding }} {{.Short}}
    {{- end}}
  {{- end}}
 {{end}}

-{{- if and (not .HasParent) .HasAvailableSubCommands}}
+{{- if (and $isRootHelp .HasAvailableSubCommands)}}
 {{usageHeader "Workspace Commands:"}}
  {{- range .Commands}}
-    {{- if (and .IsAvailableCommand (ne (index .Annotations "workspaces") ""))}}
+    {{- if (and .IsAvailableCommand (isWorkspaceCommand .))}}
  {{rpad .Name .NamePadding }} {{.Short}}
    {{- end}}
  {{- end}}
@@ -301,12 +389,12 @@ func usageTemplate() string {

 {{- if .HasAvailableLocalFlags}}
 {{usageHeader "Flags:"}}
-{{.LocalFlags.FlagUsages | trimTrailingWhitespaces}}
+{{.LocalFlags.FlagUsagesWrapped 100 | trimTrailingWhitespaces}}
 {{end}}

 {{- if .HasAvailableInheritedFlags}}
 {{usageHeader "Global Flags:"}}
-{{.InheritedFlags.FlagUsages | trimTrailingWhitespaces}}
+{{.InheritedFlags.FlagUsagesWrapped 100 | trimTrailingWhitespaces}}
 {{end}}

 {{- if .HasHelpSubCommands}}
@@ -323,8 +411,85 @@ Use "{{.CommandPath}} [command] --help" for more information about a command.
 {{end}}`
 }

+// example represents a standard example for command usage, to be used
+// with formatExamples.
+type example struct {
+	Description string
+	Command     string
+}
+
+// formatExamples formats the examples as width wrapped bulletpoint
+// descriptions with the command underneath.
+func formatExamples(examples ...example) string {
+	wrap := cliui.Styles.Wrap.Copy()
+	wrap.PaddingLeft(4)
+	var sb strings.Builder
+	for i, e := range examples {
+		if len(e.Description) > 0 {
+			_, _ = sb.WriteString("  - " + wrap.Render(e.Description + ":")[4:] + "\n\n    ")
+		}
+		// We add 1 space here because `cliui.Styles.Code` adds an extra
+		// space. This makes the code block align at an even 2 or 6
+		// spaces for symmetry.
+		_, _ = sb.WriteString(" " + cliui.Styles.Code.Render(fmt.Sprintf("$ %s", e.Command)))
+		if i < len(examples)-1 {
+			_, _ = sb.WriteString("\n\n")
+		}
+	}
+	return sb.String()
+}
+
 // FormatCobraError colorizes and adds "--help" docs to cobra commands.
 func FormatCobraError(err error, cmd *cobra.Command) string {
 	helpErrMsg := fmt.Sprintf("Run '%s --help' for usage.", cmd.CommandPath())
-	return cliui.Styles.Error.Render(err.Error() + "\n" + helpErrMsg)
+
+	var (
+		httpErr *codersdk.Error
+		output  strings.Builder
+	)
+
+	if xerrors.As(err, &httpErr) {
+		_, _ = fmt.Fprintln(&output, httpErr.Friendly())
+	}
+
+	// If the httpErr is nil then we just have a regular error in which
+	// case we want to print out what's happening.
+	if httpErr == nil || cliflag.IsSetBool(cmd, varVerbose) {
+		_, _ = fmt.Fprintln(&output, err.Error())
+	}
+
+	_, _ = fmt.Fprint(&output, helpErrMsg)
+
+	return cliui.Styles.Error.Render(output.String())
+}
+
+func checkVersions(cmd *cobra.Command, client *codersdk.Client) error {
+	if cliflag.IsSetBool(cmd, varNoVersionCheck) {
+		return nil
+	}
+
+	clientVersion := buildinfo.Version()
+
+	info, err := client.BuildInfo(cmd.Context())
+	// Avoid printing errors that are connection-related.
+	if codersdk.IsConnectionErr(err) {
+		return nil
+	}
+
+	if err != nil {
+		return xerrors.Errorf("build info: %w", err)
+	}
+
+	fmtWarningText := `version mismatch: client %s, server %s
+download the server version with: 'curl -L https://coder.com/install.sh | sh -s -- --version %s'
+`
+
+	if !buildinfo.VersionsMatch(clientVersion, info.Version) {
+		warn := cliui.Styles.Warn.Copy().Align(lipgloss.Left)
+		// Trim the leading 'v', our install.sh script does not handle this case well.
+		_, _ = fmt.Fprintf(cmd.ErrOrStderr(), warn.Render(fmtWarningText), clientVersion, info.Version, strings.TrimPrefix(info.CanonicalVersion(), "v"))
+		_, _ = fmt.Fprintln(cmd.ErrOrStderr())
+	}
+
+	return nil
 }
@@ -0,0 +1,77 @@
+package cli
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+	"go.uber.org/goleak"
+)
+
+func Test_formatExamples(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name        string
+		examples    []example
+		wantMatches []string
+	}{
+		{
+			name:        "No examples",
+			examples:    nil,
+			wantMatches: nil,
+		},
+		{
+			name: "Output examples",
+			examples: []example{
+				{
+					Description: "Hello world",
+					Command:     "echo hello",
+				},
+				{
+					Description: "Bye bye",
+					Command:     "echo bye",
+				},
+			},
+			wantMatches: []string{
+				"Hello world", "echo hello",
+				"Bye bye", "echo bye",
+			},
+		},
+		{
+			name: "No description outputs commands",
+			examples: []example{
+				{
+					Command: "echo hello",
+				},
+			},
+			wantMatches: []string{
+				"echo hello",
+			},
+		},
+	}
+	for _, tt := range tests {
+		tt := tt
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			got := formatExamples(tt.examples...)
+			if len(tt.wantMatches) == 0 {
+				require.Empty(t, got)
+			} else {
+				for _, want := range tt.wantMatches {
+					require.Contains(t, got, want)
+				}
+			}
+		})
+	}
+}
+
+func TestMain(m *testing.M) {
+	goleak.VerifyTestMain(m,
+		// The lumberjack library is used by by agent and seems to leave
+		// goroutines after Close(), fails TestGitSSH tests.
+		// https://github.com/natefinch/lumberjack/pull/100
+		goleak.IgnoreTopFunction("gopkg.in/natefinch/lumberjack%2ev2.(*Logger).millRun"),
+		goleak.IgnoreTopFunction("gopkg.in/natefinch/lumberjack%2ev2.(*Logger).mill.func1"),
+	)
+}
@@ -4,23 +4,116 @@ import (
 	"bytes"
 	"testing"

-	"github.com/coder/coder/buildinfo"
-
+	"github.com/spf13/cobra"
 	"github.com/stretchr/testify/require"
+	"golang.org/x/xerrors"

+	"github.com/coder/coder/buildinfo"
 	"github.com/coder/coder/cli"
 	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/codersdk"
 )

 func TestRoot(t *testing.T) {
+	t.Parallel()
 	t.Run("FormatCobraError", func(t *testing.T) {
 		t.Parallel()

-		cmd, _ := clitest.New(t, "delete")
+		t.Run("OK", func(t *testing.T) {
+			t.Parallel()

-		cmd, err := cmd.ExecuteC()
-		errStr := cli.FormatCobraError(err, cmd)
-		require.Contains(t, errStr, "Run 'coder delete --help' for usage.")
+			cmd, _ := clitest.New(t, "delete")
+
+			cmd, err := cmd.ExecuteC()
+			errStr := cli.FormatCobraError(err, cmd)
+			require.Contains(t, errStr, "Run 'coder delete --help' for usage.")
+		})
+
+		t.Run("Verbose", func(t *testing.T) {
+			t.Parallel()
+
+			// Test that the verbose error is masked without verbose flag.
+			t.Run("NoVerboseAPIError", func(t *testing.T) {
+				t.Parallel()
+
+				cmd, _ := clitest.New(t)
+
+				cmd.RunE = func(cmd *cobra.Command, args []string) error {
+					var err error = &codersdk.Error{
+						Response: codersdk.Response{
+							Message: "This is a message.",
+						},
+						Helper: "Try this instead.",
+					}
+
+					err = xerrors.Errorf("wrap me: %w", err)
+
+					return err
+				}
+
+				cmd, err := cmd.ExecuteC()
+				errStr := cli.FormatCobraError(err, cmd)
+				require.Contains(t, errStr, "This is a message. Try this instead.")
+				require.NotContains(t, errStr, err.Error())
+			})
+
+			// Assert that a regular error is not masked when verbose is not
+			// specified.
+			t.Run("NoVerboseRegularError", func(t *testing.T) {
+				t.Parallel()
+
+				cmd, _ := clitest.New(t)
+
+				cmd.RunE = func(cmd *cobra.Command, args []string) error {
+					return xerrors.Errorf("this is a non-codersdk error: %w", xerrors.Errorf("a wrapped error"))
+				}
+
+				cmd, err := cmd.ExecuteC()
+				errStr := cli.FormatCobraError(err, cmd)
+				require.Contains(t, errStr, err.Error())
+			})
+
+			// Test that both the friendly error and the verbose error are
+			// displayed when verbose is passed.
+			t.Run("APIError", func(t *testing.T) {
+				t.Parallel()
+
+				cmd, _ := clitest.New(t, "--verbose")
+
+				cmd.RunE = func(cmd *cobra.Command, args []string) error {
+					var err error = &codersdk.Error{
+						Response: codersdk.Response{
+							Message: "This is a message.",
+						},
+						Helper: "Try this instead.",
+					}
+
+					err = xerrors.Errorf("wrap me: %w", err)
+
+					return err
+				}
+
+				cmd, err := cmd.ExecuteC()
+				errStr := cli.FormatCobraError(err, cmd)
+				require.Contains(t, errStr, "This is a message. Try this instead.")
+				require.Contains(t, errStr, err.Error())
+			})
+
+			// Assert that a regular error is not masked when verbose specified.
+			t.Run("RegularError", func(t *testing.T) {
+				t.Parallel()
+
+				cmd, _ := clitest.New(t, "--verbose")
+
+				cmd.RunE = func(cmd *cobra.Command, args []string) error {
+					return xerrors.Errorf("this is a non-codersdk error: %w", xerrors.Errorf("a wrapped error"))
+				}
+
+				cmd, err := cmd.ExecuteC()
+				errStr := cli.FormatCobraError(err, cmd)
+				require.Contains(t, errStr, err.Error())
+			})
+		})
 	})

 	t.Run("Version", func(t *testing.T) {
@@ -17,12 +17,6 @@ import (
 )

 const (
-	scheduleDescriptionLong = `Modify scheduled stop and start times for your workspace:
-  * schedule show: show workspace schedule
-  * schedule start: edit workspace start schedule
-  * schedule stop: edit workspace stop schedule
-  * schedule override-stop: edit stop time of active workspace
-`
 	scheduleShowDescriptionLong = `Shows the following information for the given workspace:
  * The automatic start schedule
  * The next scheduled start time
@@ -64,26 +58,26 @@ func schedules() *cobra.Command {
 		Annotations: workspaceCommand,
 		Use:         "schedule { show | start | stop | override } <workspace>",
 		Short:       "Modify scheduled stop and start times for your workspace",
-		Long:        scheduleDescriptionLong,
 	}

-	scheduleCmd.AddCommand(scheduleShow())
-	scheduleCmd.AddCommand(scheduleStart())
-	scheduleCmd.AddCommand(scheduleStop())
-	scheduleCmd.AddCommand(scheduleOverride())
+	scheduleCmd.AddCommand(
+		scheduleShow(),
+		scheduleStart(),
+		scheduleStop(),
+		scheduleOverride(),
+	)

 	return scheduleCmd
 }

 func scheduleShow() *cobra.Command {
 	showCmd := &cobra.Command{
-		Annotations: workspaceCommand,
-		Use:         "show <workspace-name>",
-		Short:       "Show workspace schedule",
-		Long:        scheduleShowDescriptionLong,
-		Args:        cobra.ExactArgs(1),
+		Use:   "show <workspace-name>",
+		Short: "Show workspace schedule",
+		Long:  scheduleShowDescriptionLong,
+		Args:  cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -101,14 +95,18 @@ func scheduleShow() *cobra.Command {

 func scheduleStart() *cobra.Command {
 	cmd := &cobra.Command{
-		Annotations: workspaceCommand,
-		Use:         "start <workspace-name> { <start-time> [day-of-week] [location] | manual }",
-		Example:     `start my-workspace 9:30AM Mon-Fri Europe/Dublin`,
-		Short:       "Edit workspace start schedule",
-		Long:        scheduleStartDescriptionLong,
-		Args:        cobra.RangeArgs(2, 4),
+		Use: "start <workspace-name> { <start-time> [day-of-week] [location] | manual }",
+		Example: formatExamples(
+			example{
+				Description: "Set the workspace to start at 9:30am (in Dublin) from Monday to Friday",
+				Command:     "coder schedule start my-workspace 9:30AM Mon-Fri Europe/Dublin",
+			},
+		),
+		Short: "Edit workspace start schedule",
+		Long:  scheduleStartDescriptionLong,
+		Args:  cobra.RangeArgs(2, 4),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -148,14 +146,17 @@ func scheduleStart() *cobra.Command {

 func scheduleStop() *cobra.Command {
 	return &cobra.Command{
-		Annotations: workspaceCommand,
-		Args:        cobra.ExactArgs(2),
-		Use:         "stop <workspace-name> { <duration> | manual }",
-		Example:     `stop my-workspace 2h30m`,
-		Short:       "Edit workspace stop schedule",
-		Long:        scheduleStopDescriptionLong,
+		Args: cobra.ExactArgs(2),
+		Use:  "stop <workspace-name> { <duration> | manual }",
+		Example: formatExamples(
+			example{
+				Command: "coder schedule stop my-workspace 2h30m",
+			},
+		),
+		Short: "Edit workspace stop schedule",
+		Long:  scheduleStopDescriptionLong,
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -191,19 +192,22 @@ func scheduleStop() *cobra.Command {

 func scheduleOverride() *cobra.Command {
 	overrideCmd := &cobra.Command{
-		Args:        cobra.ExactArgs(2),
-		Annotations: workspaceCommand,
-		Use:         "override-stop <workspace-name> <duration from now>",
-		Example:     "override-stop my-workspace 90m",
-		Short:       "Edit stop time of active workspace",
-		Long:        scheduleOverrideDescriptionLong,
+		Args: cobra.ExactArgs(2),
+		Use:  "override-stop <workspace-name> <duration from now>",
+		Example: formatExamples(
+			example{
+				Command: "coder schedule override-stop my-workspace 90m",
+			},
+		),
+		Short: "Edit stop time of active workspace",
+		Long:  scheduleOverrideDescriptionLong,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			overrideDuration, err := parseDuration(args[1])
 			if err != nil {
 				return err
 			}

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return xerrors.Errorf("create client: %w", err)
 			}
@@ -276,8 +280,8 @@ func displaySchedule(workspace codersdk.Workspace, out io.Writer) error {
 		if workspace.LatestBuild.Transition != "start" {
 			schedNextStop = "-"
 		} else {
-			schedNextStop = workspace.LatestBuild.Deadline.In(loc).Format(timeFormat + " on " + dateFormat)
-			schedNextStop = fmt.Sprintf("%s (in %s)", schedNextStop, durationDisplay(time.Until(workspace.LatestBuild.Deadline)))
+			schedNextStop = workspace.LatestBuild.Deadline.Time.In(loc).Format(timeFormat + " on " + dateFormat)
+			schedNextStop = fmt.Sprintf("%s (in %s)", schedNextStop, durationDisplay(time.Until(workspace.LatestBuild.Deadline.Time)))
 		}
 	}

@@ -239,7 +239,7 @@ func TestScheduleOverride(t *testing.T) {

 		// Assert test invariant: workspace build has a deadline set equal to now plus ttl
 		initDeadline := time.Now().Add(time.Duration(*workspace.TTLMillis) * time.Millisecond)
-		require.WithinDuration(t, initDeadline, workspace.LatestBuild.Deadline, time.Minute)
+		require.WithinDuration(t, initDeadline, workspace.LatestBuild.Deadline.Time, time.Minute)

 		cmd, root := clitest.New(t, cmdArgs...)
 		clitest.SetupConfig(t, client, root)
@@ -252,7 +252,7 @@ func TestScheduleOverride(t *testing.T) {
 		// Then: the deadline of the latest build is updated assuming the units are minutes
 		updated, err := client.Workspace(ctx, workspace.ID)
 		require.NoError(t, err)
-		require.WithinDuration(t, expectedDeadline, updated.LatestBuild.Deadline, time.Minute)
+		require.WithinDuration(t, expectedDeadline, updated.LatestBuild.Deadline.Time, time.Minute)
 	})

 	t.Run("InvalidDuration", func(t *testing.T) {
@@ -279,7 +279,7 @@ func TestScheduleOverride(t *testing.T) {

 		// Assert test invariant: workspace build has a deadline set equal to now plus ttl
 		initDeadline := time.Now().Add(time.Duration(*workspace.TTLMillis) * time.Millisecond)
-		require.WithinDuration(t, initDeadline, workspace.LatestBuild.Deadline, time.Minute)
+		require.WithinDuration(t, initDeadline, workspace.LatestBuild.Deadline.Time, time.Minute)

 		cmd, root := clitest.New(t, cmdArgs...)
 		clitest.SetupConfig(t, client, root)
@@ -1,6 +1,7 @@
 package cli_test

 import (
+	"bufio"
 	"context"
 	"crypto/ecdsa"
 	"crypto/elliptic"
@@ -10,6 +11,7 @@ import (
 	"crypto/x509/pkix"
 	"encoding/json"
 	"encoding/pem"
+	"fmt"
 	"math/big"
 	"net"
 	"net/http"
@@ -17,6 +19,7 @@ import (
 	"net/url"
 	"os"
 	"runtime"
+	"strconv"
 	"strings"
 	"testing"
 	"time"
@@ -27,13 +30,16 @@ import (
 	"go.uber.org/goleak"

 	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/cli/config"
 	"github.com/coder/coder/coderd/database/postgres"
 	"github.com/coder/coder/coderd/telemetry"
 	"github.com/coder/coder/codersdk"
+	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 // This cannot be ran in parallel because it uses a signal.
-// nolint:paralleltest
+// nolint:tparallel,paralleltest
 func TestServer(t *testing.T) {
 	t.Run("Production", func(t *testing.T) {
 		if runtime.GOOS != "linux" || testing.Short() {
@@ -45,22 +51,20 @@ func TestServer(t *testing.T) {
 		defer closeFunc()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, cfg := clitest.New(t, "server", "--address", ":0", "--postgres-url", connectionURL)
-		errC := make(chan error)
+
+		root, cfg := clitest.New(t,
+			"server",
+			"--address", ":0",
+			"--postgres-url", connectionURL,
+			"--cache-dir", t.TempDir(),
+		)
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()
-		var client *codersdk.Client
-		require.Eventually(t, func() bool {
-			rawURL, err := cfg.URL().Read()
-			if err != nil {
-				return false
-			}
-			accessURL, err := url.Parse(rawURL)
-			assert.NoError(t, err)
-			client = codersdk.New(accessURL)
-			return true
-		}, time.Minute, 50*time.Millisecond)
+		accessURL := waitAccessURL(t, cfg)
+		client := codersdk.New(accessURL)
+
 		_, err = client.CreateFirstUser(ctx, codersdk.CreateFirstUserRequest{
 			Email:            "some@one.com",
 			Username:         "example",
@@ -77,26 +81,98 @@ func TestServer(t *testing.T) {
 			t.SkipNow()
 		}
 		ctx, cancelFunc := context.WithCancel(context.Background())
-		root, cfg := clitest.New(t, "server", "--address", ":0")
-		errC := make(chan error)
+		defer cancelFunc()
+
+		root, cfg := clitest.New(t,
+			"server",
+			"--address", ":0",
+			"--cache-dir", t.TempDir(),
+		)
+		pty := ptytest.New(t)
+		root.SetOutput(pty.Output())
+		root.SetErr(pty.Output())
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()
+		//nolint:gocritic // Embedded postgres take a while to fire up.
 		require.Eventually(t, func() bool {
-			_, err := cfg.URL().Read()
-			return err == nil
-		}, time.Minute, 25*time.Millisecond)
+			rawURL, err := cfg.URL().Read()
+			return err == nil && rawURL != ""
+		}, 3*time.Minute, testutil.IntervalFast, "failed to get access URL")
 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
 	})
 	t.Run("BuiltinPostgresURL", func(t *testing.T) {
 		t.Parallel()
 		root, _ := clitest.New(t, "server", "postgres-builtin-url")
-		var buf strings.Builder
-		root.SetOutput(&buf)
+		pty := ptytest.New(t)
+		root.SetOutput(pty.Output())
 		err := root.Execute()
 		require.NoError(t, err)
-		require.Contains(t, buf.String(), "psql")
+
+		pty.ExpectMatch("psql")
+	})
+
+	// Validate that an http scheme is prepended to a loopback
+	// access URL and that a warning is printed that it may not be externally
+	// reachable.
+	t.Run("NoSchemeLocalAccessURL", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancelFunc := context.WithCancel(context.Background())
+		defer cancelFunc()
+
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--access-url", "localhost:3000/",
+			"--cache-dir", t.TempDir(),
+		)
+		buf := newThreadSafeBuffer()
+		root.SetOutput(buf)
+		errC := make(chan error, 1)
+		go func() {
+			errC <- root.ExecuteContext(ctx)
+		}()
+
+		// Just wait for startup
+		_ = waitAccessURL(t, cfg)
+
+		cancelFunc()
+		require.ErrorIs(t, <-errC, context.Canceled)
+		require.Contains(t, buf.String(), "this may cause unexpected problems when creating workspaces")
+		require.Contains(t, buf.String(), "View the Web UI: http://localhost:3000/\n")
+	})
+
+	// Validate that an https scheme is prepended to a remote access URL
+	// and that a warning is printed for a host that cannot be resolved.
+	t.Run("NoSchemeRemoteAccessURL", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancelFunc := context.WithCancel(context.Background())
+		defer cancelFunc()
+
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--access-url", "foobarbaz.mydomain",
+			"--cache-dir", t.TempDir(),
+		)
+		buf := newThreadSafeBuffer()
+		root.SetOutput(buf)
+		errC := make(chan error, 1)
+		go func() {
+			errC <- root.ExecuteContext(ctx)
+		}()
+
+		// Just wait for startup
+		_ = waitAccessURL(t, cfg)
+
+		cancelFunc()
+		require.ErrorIs(t, <-errC, context.Canceled)
+		require.Contains(t, buf.String(), "this may cause unexpected problems when creating workspaces")
+		require.Contains(t, buf.String(), "View the Web UI: https://foobarbaz.mydomain\n")
 	})

 	t.Run("NoWarningWithRemoteAccessURL", func(t *testing.T) {
@@ -104,33 +180,42 @@ func TestServer(t *testing.T) {
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()

-		root, cfg := clitest.New(t, "server", "--in-memory", "--address", ":0", "--access-url", "http://1.2.3.4:3000/")
-		var buf strings.Builder
-		errC := make(chan error)
-		root.SetOutput(&buf)
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--access-url", "https://google.com",
+			"--cache-dir", t.TempDir(),
+		)
+		buf := newThreadSafeBuffer()
+		root.SetOutput(buf)
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()

 		// Just wait for startup
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
+		_ = waitAccessURL(t, cfg)

 		cancelFunc()
 		require.ErrorIs(t, <-errC, context.Canceled)
-
-		assert.NotContains(t, buf.String(), "Workspaces must be able to reach Coder from this URL")
+		require.NotContains(t, buf.String(), "this may cause unexpected problems when creating workspaces")
+		require.Contains(t, buf.String(), "View the Web UI: https://google.com\n")
 	})

 	t.Run("TLSBadVersion", func(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--in-memory", "--address", ":0",
-			"--tls-enable", "--tls-min-version", "tls9")
+
+		root, _ := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--tls-enable",
+			"--tls-min-version", "tls9",
+			"--cache-dir", t.TempDir(),
+		)
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
 	})
@@ -138,8 +223,15 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--in-memory", "--address", ":0",
-			"--tls-enable", "--tls-client-auth", "something")
+
+		root, _ := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--tls-enable",
+			"--tls-client-auth", "something",
+			"--cache-dir", t.TempDir(),
+		)
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
 	})
@@ -147,8 +239,14 @@ func TestServer(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--in-memory", "--address", ":0",
-			"--tls-enable")
+
+		root, _ := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--tls-enable",
+			"--cache-dir", t.TempDir(),
+		)
 		err := root.ExecuteContext(ctx)
 		require.Error(t, err)
 	})
@@ -158,22 +256,22 @@ func TestServer(t *testing.T) {
 		defer cancelFunc()

 		certPath, keyPath := generateTLSCertificate(t)
-		root, cfg := clitest.New(t, "server", "--in-memory", "--address", ":0",
-			"--tls-enable", "--tls-cert-file", certPath, "--tls-key-file", keyPath)
-		errC := make(chan error)
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--tls-enable",
+			"--tls-cert-file", certPath,
+			"--tls-key-file", keyPath,
+			"--cache-dir", t.TempDir(),
+		)
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()

 		// Verify HTTPS
-		var accessURLRaw string
-		require.Eventually(t, func() bool {
-			var err error
-			accessURLRaw, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)
-		accessURL, err := url.Parse(accessURLRaw)
-		require.NoError(t, err)
+		accessURL := waitAccessURL(t, cfg)
 		require.Equal(t, "https", accessURL.Scheme)
 		client := codersdk.New(accessURL)
 		client.HTTPClient = &http.Client{
@@ -184,7 +282,7 @@ func TestServer(t *testing.T) {
 				},
 			},
 		}
-		_, err = client.HasFirstUser(ctx)
+		_, err := client.HasFirstUser(ctx)
 		require.NoError(t, err)

 		cancelFunc()
@@ -199,37 +297,41 @@ func TestServer(t *testing.T) {
 		}
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, cfg := clitest.New(t, "server", "--in-memory", "--address", ":0", "--provisioner-daemons", "1")
-		serverErr := make(chan error)
-		go func() {
-			err := root.ExecuteContext(ctx)
-			serverErr <- err
-		}()
-		require.Eventually(t, func() bool {
-			var err error
-			_, err = cfg.URL().Read()
-			return err == nil
-		}, 15*time.Second, 25*time.Millisecond)

+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--provisioner-daemons", "1",
+			"--cache-dir", t.TempDir(),
+		)
+		serverErr := make(chan error, 1)
+		go func() {
+			serverErr <- root.ExecuteContext(ctx)
+		}()
+		_ = waitAccessURL(t, cfg)
 		currentProcess, err := os.FindProcess(os.Getpid())
 		require.NoError(t, err)
 		err = currentProcess.Signal(os.Interrupt)
 		require.NoError(t, err)
-		// Send a two more signal, which should be ignored.  Send 2 because the channel has a buffer
-		// of 1 and we want to make sure that nothing strange happens if we exceed the buffer.
-		err = currentProcess.Signal(os.Interrupt)
-		require.NoError(t, err)
-		err = currentProcess.Signal(os.Interrupt)
-		require.NoError(t, err)
+		// We cannot send more signals here, because it's possible Coder
+		// has already exited, which could cause the test to fail due to interrupt.
 		err = <-serverErr
-		require.NoError(t, err)
+		require.ErrorIs(t, err, context.Canceled)
 	})
 	t.Run("TracerNoLeak", func(t *testing.T) {
 		t.Parallel()
 		ctx, cancelFunc := context.WithCancel(context.Background())
 		defer cancelFunc()
-		root, _ := clitest.New(t, "server", "--in-memory", "--address", ":0", "--trace=true")
-		errC := make(chan error)
+
+		root, _ := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--trace=true",
+			"--cache-dir", t.TempDir(),
+		)
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()
@@ -257,16 +359,119 @@ func TestServer(t *testing.T) {
 			snapshot <- ss
 		})
 		server := httptest.NewServer(r)
-		t.Cleanup(server.Close)
+		defer server.Close()

-		root, _ := clitest.New(t, "server", "--in-memory", "--address", ":0", "--telemetry", "--telemetry-url", server.URL)
-		errC := make(chan error)
+		root, _ := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--telemetry",
+			"--telemetry-url", server.URL,
+			"--cache-dir", t.TempDir(),
+		)
+		errC := make(chan error, 1)
 		go func() {
 			errC <- root.ExecuteContext(ctx)
 		}()

 		<-deployment
 		<-snapshot
+		cancelFunc()
+		<-errC
+	})
+	t.Run("Prometheus", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancelFunc := context.WithCancel(context.Background())
+		defer cancelFunc()
+
+		random, err := net.Listen("tcp", "127.0.0.1:0")
+		require.NoError(t, err)
+		_ = random.Close()
+		tcpAddr, valid := random.Addr().(*net.TCPAddr)
+		require.True(t, valid)
+		randomPort := tcpAddr.Port
+
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--provisioner-daemons", "1",
+			"--prometheus-enable",
+			"--prometheus-address", ":"+strconv.Itoa(randomPort),
+			"--cache-dir", t.TempDir(),
+		)
+		serverErr := make(chan error, 1)
+		go func() {
+			serverErr <- root.ExecuteContext(ctx)
+		}()
+		_ = waitAccessURL(t, cfg)
+
+		var res *http.Response
+		require.Eventually(t, func() bool {
+			req, err := http.NewRequestWithContext(ctx, "GET", fmt.Sprintf("http://127.0.0.1:%d", randomPort), nil)
+			assert.NoError(t, err)
+			// nolint:bodyclose
+			res, err = http.DefaultClient.Do(req)
+			return err == nil
+		}, testutil.WaitShort, testutil.IntervalFast)
+
+		scanner := bufio.NewScanner(res.Body)
+		hasActiveUsers := false
+		hasWorkspaces := false
+		for scanner.Scan() {
+			// This metric is manually registered to be tracked in the server. That's
+			// why we test it's tracked here.
+			if strings.HasPrefix(scanner.Text(), "coderd_api_active_users_duration_hour") {
+				hasActiveUsers = true
+				continue
+			}
+			if strings.HasPrefix(scanner.Text(), "coderd_api_workspace_latest_build_total") {
+				hasWorkspaces = true
+				continue
+			}
+			t.Logf("scanned %s", scanner.Text())
+		}
+		require.NoError(t, scanner.Err())
+		require.True(t, hasActiveUsers)
+		require.True(t, hasWorkspaces)
+		cancelFunc()
+		<-serverErr
+	})
+	t.Run("GitHubOAuth", func(t *testing.T) {
+		t.Parallel()
+		ctx, cancelFunc := context.WithCancel(context.Background())
+		defer cancelFunc()
+
+		fakeRedirect := "https://fake-url.com"
+		root, cfg := clitest.New(t,
+			"server",
+			"--in-memory",
+			"--address", ":0",
+			"--oauth2-github-client-id", "fake",
+			"--oauth2-github-client-secret", "fake",
+			"--oauth2-github-enterprise-base-url", fakeRedirect,
+		)
+		serverErr := make(chan error, 1)
+		go func() {
+			serverErr <- root.ExecuteContext(ctx)
+		}()
+		accessURL := waitAccessURL(t, cfg)
+		client := codersdk.New(accessURL)
+		client.HTTPClient.CheckRedirect = func(req *http.Request, via []*http.Request) error {
+			return http.ErrUseLastResponse
+		}
+		githubURL, err := accessURL.Parse("/api/v2/users/oauth2/github")
+		require.NoError(t, err)
+		req, err := http.NewRequestWithContext(ctx, http.MethodGet, githubURL.String(), nil)
+		require.NoError(t, err)
+		res, err := client.HTTPClient.Do(req)
+		require.NoError(t, err)
+		defer res.Body.Close()
+		fakeURL, err := res.Location()
+		require.NoError(t, err)
+		require.True(t, strings.HasPrefix(fakeURL.String(), fakeRedirect), fakeURL.String())
+		cancelFunc()
+		<-serverErr
 	})
 }

@@ -304,3 +509,19 @@ func generateTLSCertificate(t testing.TB) (certPath, keyPath string) {
 	require.NoError(t, err)
 	return certFile.Name(), keyFile.Name()
 }
+
+func waitAccessURL(t *testing.T, cfg config.Root) *url.URL {
+	t.Helper()
+
+	var err error
+	var rawURL string
+	require.Eventually(t, func() bool {
+		rawURL, err = cfg.URL().Read()
+		return err == nil && rawURL != ""
+	}, testutil.WaitLong, testutil.IntervalFast, "failed to get access URL")
+
+	accessURL, err := url.Parse(rawURL)
+	require.NoError(t, err, "failed to parse access URL")
+
+	return accessURL
+}
@@ -10,11 +10,11 @@ import (
 func show() *cobra.Command {
 	return &cobra.Command{
 		Annotations: workspaceCommand,
-		Use:         "show",
+		Use:         "show <workspace>",
 		Short:       "Show details of a workspace's resources and agents",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -0,0 +1,14 @@
+//go:build !windows
+
+package cli
+
+import (
+	"os"
+	"syscall"
+)
+
+var interruptSignals = []os.Signal{
+	os.Interrupt,
+	syscall.SIGTERM,
+	syscall.SIGHUP,
+}
@@ -0,0 +1,9 @@
+//go:build windows
+
+package cli
+
+import (
+	"os"
+)
+
+var interruptSignals = []os.Signal{os.Interrupt}
@@ -2,6 +2,7 @@ package cli

 import (
 	"context"
+	"errors"
 	"fmt"
 	"io"
 	"os"
@@ -18,17 +19,24 @@ import (
 	gosshagent "golang.org/x/crypto/ssh/agent"
 	"golang.org/x/term"
 	"golang.org/x/xerrors"
+	"inet.af/netaddr"
+	tslogger "tailscale.com/types/logger"

+	"cdr.dev/slog"
+	"cdr.dev/slog/sloggers/sloghuman"
 	"github.com/coder/coder/cli/cliflag"
 	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/coderd/autobuild/notify"
 	"github.com/coder/coder/coderd/util/ptr"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/cryptorand"
+	"github.com/coder/coder/peer/peerwg"
 )

-var workspacePollInterval = time.Minute
-var autostopNotifyCountdown = []time.Duration{30 * time.Minute}
+var (
+	workspacePollInterval   = time.Minute
+	autostopNotifyCountdown = []time.Duration{30 * time.Minute}
+)

 func ssh() *cobra.Command {
 	var (
@@ -37,6 +45,7 @@ func ssh() *cobra.Command {
 		forwardAgent   bool
 		identityAgent  string
 		wsPollInterval time.Duration
+		wireguard      bool
 	)
 	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
@@ -44,7 +53,10 @@ func ssh() *cobra.Command {
 		Short:       "SSH into a workspace",
 		Args:        cobra.ArbitraryArgs,
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			ctx, cancel := context.WithCancel(cmd.Context())
+			defer cancel()
+
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -61,52 +73,121 @@ func ssh() *cobra.Command {
 				}
 			}

-			workspace, agent, err := getWorkspaceAndAgent(cmd, client, codersdk.Me, args[0], shuffle)
+			workspace, workspaceAgent, err := getWorkspaceAndAgent(ctx, cmd, client, codersdk.Me, args[0], shuffle)
 			if err != nil {
 				return err
 			}

 			// OpenSSH passes stderr directly to the calling TTY.
 			// This is required in "stdio" mode so a connecting indicator can be displayed.
-			err = cliui.Agent(cmd.Context(), cmd.ErrOrStderr(), cliui.AgentOptions{
+			err = cliui.Agent(ctx, cmd.ErrOrStderr(), cliui.AgentOptions{
 				WorkspaceName: workspace.Name,
 				Fetch: func(ctx context.Context) (codersdk.WorkspaceAgent, error) {
-					return client.WorkspaceAgent(ctx, agent.ID)
+					return client.WorkspaceAgent(ctx, workspaceAgent.ID)
 				},
 			})
 			if err != nil {
 				return xerrors.Errorf("await agent: %w", err)
 			}

-			conn, err := client.DialWorkspaceAgent(cmd.Context(), agent.ID, nil)
-			if err != nil {
-				return err
-			}
-			defer conn.Close()
+			var newSSHClient func() (*gossh.Client, error)

-			stopPolling := tryPollWorkspaceAutostop(cmd.Context(), client, workspace)
-			defer stopPolling()
-
-			if stdio {
-				rawSSH, err := conn.SSH()
+			if !wireguard {
+				conn, err := client.DialWorkspaceAgent(ctx, workspaceAgent.ID, nil)
 				if err != nil {
 					return err
 				}
-				go func() {
-					_, _ = io.Copy(cmd.OutOrStdout(), rawSSH)
-				}()
-				_, _ = io.Copy(rawSSH, cmd.InOrStdin())
-				return nil
+				defer conn.Close()
+
+				stopPolling := tryPollWorkspaceAutostop(ctx, client, workspace)
+				defer stopPolling()
+
+				if stdio {
+					rawSSH, err := conn.SSH()
+					if err != nil {
+						return err
+					}
+					defer rawSSH.Close()
+
+					go func() {
+						_, _ = io.Copy(cmd.OutOrStdout(), rawSSH)
+					}()
+					_, _ = io.Copy(rawSSH, cmd.InOrStdin())
+					return nil
+				}
+
+				newSSHClient = conn.SSHClient
+			} else {
+				// TODO: more granual control of Tailscale logging.
+				peerwg.Logf = tslogger.Discard
+
+				ipv6 := peerwg.UUIDToNetaddr(uuid.New())
+				wgn, err := peerwg.New(
+					slog.Make(sloghuman.Sink(cmd.ErrOrStderr())),
+					[]netaddr.IPPrefix{netaddr.IPPrefixFrom(ipv6, 128)},
+				)
+				if err != nil {
+					return xerrors.Errorf("create wireguard network: %w", err)
+				}
+				defer wgn.Close()
+
+				err = client.PostWireguardPeer(ctx, workspace.ID, peerwg.Handshake{
+					Recipient:      workspaceAgent.ID,
+					NodePublicKey:  wgn.NodePrivateKey.Public(),
+					DiscoPublicKey: wgn.DiscoPublicKey,
+					IPv6:           ipv6,
+				})
+				if err != nil {
+					return xerrors.Errorf("post wireguard peer: %w", err)
+				}
+
+				err = wgn.AddPeer(peerwg.Handshake{
+					Recipient:      workspaceAgent.ID,
+					DiscoPublicKey: workspaceAgent.DiscoPublicKey,
+					NodePublicKey:  workspaceAgent.WireguardPublicKey,
+					IPv6:           workspaceAgent.IPv6.IP(),
+				})
+				if err != nil {
+					return xerrors.Errorf("add workspace agent as peer: %w", err)
+				}
+
+				if stdio {
+					rawSSH, err := wgn.SSH(ctx, workspaceAgent.IPv6.IP())
+					if err != nil {
+						return err
+					}
+					defer rawSSH.Close()
+
+					go func() {
+						_, _ = io.Copy(cmd.OutOrStdout(), rawSSH)
+					}()
+					_, _ = io.Copy(rawSSH, cmd.InOrStdin())
+					return nil
+				}
+
+				newSSHClient = func() (*gossh.Client, error) {
+					return wgn.SSHClient(ctx, workspaceAgent.IPv6.IP())
+				}
 			}
-			sshClient, err := conn.SSHClient()
+
+			sshClient, err := newSSHClient()
 			if err != nil {
 				return err
 			}
+			defer sshClient.Close()

 			sshSession, err := sshClient.NewSession()
 			if err != nil {
 				return err
 			}
+			defer sshSession.Close()
+
+			// Ensure context cancellation is propagated to the
+			// SSH session, e.g. to cancel `Wait()` at the end.
+			go func() {
+				<-ctx.Done()
+				_ = sshSession.Close()
+			}()

 			if identityAgent == "" {
 				identityAgent = os.Getenv("SSH_AUTH_SOCK")
@@ -122,25 +203,29 @@ func ssh() *cobra.Command {
 				}
 			}

-			stdoutFile, valid := cmd.OutOrStdout().(*os.File)
-			if valid && isatty.IsTerminal(stdoutFile.Fd()) {
-				state, err := term.MakeRaw(int(os.Stdin.Fd()))
+			stdoutFile, validOut := cmd.OutOrStdout().(*os.File)
+			stdinFile, validIn := cmd.InOrStdin().(*os.File)
+			if validOut && validIn && isatty.IsTerminal(stdoutFile.Fd()) {
+				state, err := term.MakeRaw(int(stdinFile.Fd()))
 				if err != nil {
 					return err
 				}
 				defer func() {
-					_ = term.Restore(int(os.Stdin.Fd()), state)
+					_ = term.Restore(int(stdinFile.Fd()), state)
 				}()

-				windowChange := listenWindowSize(cmd.Context())
+				windowChange := listenWindowSize(ctx)
 				go func() {
 					for {
 						select {
-						case <-cmd.Context().Done():
+						case <-ctx.Done():
 							return
 						case <-windowChange:
 						}
-						width, height, _ := term.GetSize(int(stdoutFile.Fd()))
+						width, height, err := term.GetSize(int(stdoutFile.Fd()))
+						if err != nil {
+							continue
+						}
 						_ = sshSession.WindowChange(height, width)
 					}
 				}()
@@ -153,15 +238,24 @@ func ssh() *cobra.Command {

 			sshSession.Stdin = cmd.InOrStdin()
 			sshSession.Stdout = cmd.OutOrStdout()
-			sshSession.Stderr = cmd.OutOrStdout()
+			sshSession.Stderr = cmd.ErrOrStderr()

 			err = sshSession.Shell()
 			if err != nil {
 				return err
 			}

+			// Put cancel at the top of the defer stack to initiate
+			// shutdown of services.
+			defer cancel()
+
 			err = sshSession.Wait()
 			if err != nil {
+				// If the connection drops unexpectedly, we get an ExitMissingError but no other
+				// error details, so try to at least give the user a better message
+				if errors.Is(err, &gossh.ExitMissingError{}) {
+					return xerrors.New("SSH connection ended unexpectedly")
+				}
 				return err
 			}

@@ -174,6 +268,8 @@ func ssh() *cobra.Command {
 	cliflag.BoolVarP(cmd.Flags(), &forwardAgent, "forward-agent", "A", "CODER_SSH_FORWARD_AGENT", false, "Specifies whether to forward the SSH agent specified in $SSH_AUTH_SOCK")
 	cliflag.StringVarP(cmd.Flags(), &identityAgent, "identity-agent", "", "CODER_SSH_IDENTITY_AGENT", "", "Specifies which identity agent to use (overrides $SSH_AUTH_SOCK), forward agent must also be enabled")
 	cliflag.DurationVarP(cmd.Flags(), &wsPollInterval, "workspace-poll-interval", "", "CODER_WORKSPACE_POLL_INTERVAL", workspacePollInterval, "Specifies how often to poll for workspace automated shutdown.")
+	cliflag.BoolVarP(cmd.Flags(), &wireguard, "wireguard", "", "CODER_SSH_WIREGUARD", false, "Whether to use Wireguard for SSH tunneling.")
+	_ = cmd.Flags().MarkHidden("wireguard")

 	return cmd
 }
@@ -181,16 +277,14 @@ func ssh() *cobra.Command {
 // getWorkspaceAgent returns the workspace and agent selected using either the
 // `<workspace>[.<agent>]` syntax via `in` or picks a random workspace and agent
 // if `shuffle` is true.
-func getWorkspaceAndAgent(cmd *cobra.Command, client *codersdk.Client, userID string, in string, shuffle bool) (codersdk.Workspace, codersdk.WorkspaceAgent, error) { //nolint:revive
-	ctx := cmd.Context()
-
+func getWorkspaceAndAgent(ctx context.Context, cmd *cobra.Command, client *codersdk.Client, userID string, in string, shuffle bool) (codersdk.Workspace, codersdk.WorkspaceAgent, error) { //nolint:revive
 	var (
 		workspace      codersdk.Workspace
 		workspaceParts = strings.Split(in, ".")
 		err            error
 	)
 	if shuffle {
-		workspaces, err := client.Workspaces(cmd.Context(), codersdk.WorkspaceFilter{
+		workspaces, err := client.Workspaces(ctx, codersdk.WorkspaceFilter{
 			Owner: codersdk.Me,
 		})
 		if err != nil {
@@ -293,7 +387,7 @@ func notifyCondition(ctx context.Context, client *codersdk.Client, workspaceID u
 			return time.Time{}, nil
 		}

-		deadline = ws.LatestBuild.Deadline
+		deadline = ws.LatestBuild.Deadline.Time
 		callback = func() {
 			ttl := deadline.Sub(now)
 			var title, body string
@@ -29,6 +29,7 @@ import (
 	"github.com/coder/coder/provisioner/echo"
 	"github.com/coder/coder/provisionersdk/proto"
 	"github.com/coder/coder/pty/ptytest"
+	"github.com/coder/coder/testutil"
 )

 func setupWorkspaceForSSH(t *testing.T) (*codersdk.Client, codersdk.Workspace, string) {
@@ -59,6 +60,7 @@ func setupWorkspaceForSSH(t *testing.T) (*codersdk.Client, codersdk.Workspace, s
 	coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 	template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
 	workspace := coderdtest.CreateWorkspace(t, client, user.OrganizationID, template.ID)
+	coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)

 	return client, workspace, agentToken
 }
@@ -67,6 +69,7 @@ func TestSSH(t *testing.T) {
 	t.Parallel()
 	t.Run("ImmediateExit", func(t *testing.T) {
 		t.Parallel()
+
 		client, workspace, agentToken := setupWorkspaceForSSH(t)
 		cmd, root := clitest.New(t, "ssh", workspace.Name)
 		clitest.SetupConfig(t, client, root)
@@ -74,20 +77,24 @@ func TestSSH(t *testing.T) {
 		cmd.SetIn(pty.Input())
 		cmd.SetErr(pty.Output())
 		cmd.SetOut(pty.Output())
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+		defer cancel()
+
 		cmdDone := tGo(t, func() {
-			err := cmd.Execute()
+			err := cmd.ExecuteContext(ctx)
 			assert.NoError(t, err)
 		})
 		pty.ExpectMatch("Waiting")
-		coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
+
 		agentClient := codersdk.New(client.URL)
 		agentClient.SessionToken = agentToken
 		agentCloser := agent.New(agentClient.ListenWorkspaceAgent, &agent.Options{
 			Logger: slogtest.Make(t, nil).Leveled(slog.LevelDebug),
 		})
-		t.Cleanup(func() {
+		defer func() {
 			_ = agentCloser.Close()
-		})
+		}()

 		// Shells on Mac, Windows, and Linux all exit shells with the "exit" command.
 		pty.WriteLine("exit")
@@ -96,11 +103,9 @@ func TestSSH(t *testing.T) {
 	t.Run("Stdio", func(t *testing.T) {
 		t.Parallel()
 		client, workspace, agentToken := setupWorkspaceForSSH(t)
-
 		_, _ = tGoContext(t, func(ctx context.Context) {
 			// Run this async so the SSH command has to wait for
 			// the build and agent to connect!
-			coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
 			agentClient := codersdk.New(client.URL)
 			agentClient.SessionToken = agentToken
 			agentCloser := agent.New(agentClient.ListenWorkspaceAgent, &agent.Options{
@@ -112,6 +117,14 @@ func TestSSH(t *testing.T) {

 		clientOutput, clientInput := io.Pipe()
 		serverOutput, serverInput := io.Pipe()
+		defer func() {
+			for _, c := range []io.Closer{clientOutput, clientInput, serverOutput, serverInput} {
+				_ = c.Close()
+			}
+		}()
+
+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+		defer cancel()

 		cmd, root := clitest.New(t, "ssh", "--stdio", workspace.Name)
 		clitest.SetupConfig(t, client, root)
@@ -119,7 +132,7 @@ func TestSSH(t *testing.T) {
 		cmd.SetOut(serverInput)
 		cmd.SetErr(io.Discard)
 		cmdDone := tGo(t, func() {
-			err := cmd.Execute()
+			err := cmd.ExecuteContext(ctx)
 			assert.NoError(t, err)
 		})

@@ -131,9 +144,13 @@ func TestSSH(t *testing.T) {
 			HostKeyCallback: ssh.InsecureIgnoreHostKey(),
 		})
 		require.NoError(t, err)
+		defer conn.Close()
+
 		sshClient := ssh.NewClient(conn, channels, requests)
 		session, err := sshClient.NewSession()
 		require.NoError(t, err)
+		defer session.Close()
+
 		command := "sh -c exit"
 		if runtime.GOOS == "windows" {
 			command = "cmd.exe /c exit"
@@ -155,18 +172,12 @@ func TestSSH(t *testing.T) {

 		client, workspace, agentToken := setupWorkspaceForSSH(t)

-		_, _ = tGoContext(t, func(ctx context.Context) {
-			// Run this async so the SSH command has to wait for
-			// the build and agent to connect!
-			coderdtest.AwaitWorkspaceBuildJob(t, client, workspace.LatestBuild.ID)
-			agentClient := codersdk.New(client.URL)
-			agentClient.SessionToken = agentToken
-			agentCloser := agent.New(agentClient.ListenWorkspaceAgent, &agent.Options{
-				Logger: slogtest.Make(t, nil).Leveled(slog.LevelDebug),
-			})
-			<-ctx.Done()
-			_ = agentCloser.Close()
+		agentClient := codersdk.New(client.URL)
+		agentClient.SessionToken = agentToken
+		agentCloser := agent.New(agentClient.ListenWorkspaceAgent, &agent.Options{
+			Logger: slogtest.Make(t, nil).Leveled(slog.LevelDebug),
 		})
+		defer agentCloser.Close()

 		// Generate private key.
 		privateKey, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
@@ -187,18 +198,22 @@ func TestSSH(t *testing.T) {
 				fd, err := l.Accept()
 				if err != nil {
 					if !errors.Is(err, net.ErrClosed) {
-						t.Logf("accept error: %v", err)
+						assert.NoError(t, err, "listener accept failed")
 					}
 					return
 				}

 				err = gosshagent.ServeAgent(kr, fd)
 				if !errors.Is(err, io.EOF) {
-					assert.NoError(t, err)
+					assert.NoError(t, err, "serve agent failed")
 				}
+				_ = fd.Close()
 			}
 		})

+		ctx, cancel := context.WithTimeout(context.Background(), testutil.WaitLong)
+		defer cancel()
+
 		cmd, root := clitest.New(t,
 			"ssh",
 			workspace.Name,
@@ -209,10 +224,10 @@ func TestSSH(t *testing.T) {
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
 		cmd.SetOut(pty.Output())
-		cmd.SetErr(io.Discard)
+		cmd.SetErr(pty.Output())
 		cmdDone := tGo(t, func() {
-			err := cmd.Execute()
-			assert.NoError(t, err)
+			err := cmd.ExecuteContext(ctx)
+			assert.NoError(t, err, "ssh command failed")
 		})

 		// Ensure that SSH_AUTH_SOCK is set.
@@ -223,7 +238,7 @@ func TestSSH(t *testing.T) {
 		// Ensure that ssh-add lists our key.
 		pty.WriteLine("ssh-add -L")
 		keys, err := kr.List()
-		require.NoError(t, err)
+		require.NoError(t, err, "list keys failed")
 		pty.ExpectMatch(keys[0].String())

 		// And we're done.
@@ -1,6 +1,7 @@
 package cli

 import (
+	"fmt"
 	"time"

 	"github.com/spf13/cobra"
@@ -16,15 +17,7 @@ func start() *cobra.Command {
 		Short:       "Build a workspace with the start state",
 		Args:        cobra.ExactArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			_, err := cliui.Prompt(cmd, cliui.PromptOptions{
-				Text:      "Confirm start workspace?",
-				IsConfirm: true,
-			})
-			if err != nil {
-				return err
-			}
-
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -39,7 +32,14 @@ func start() *cobra.Command {
 			if err != nil {
 				return err
 			}
-			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+
+			err = cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+			if err != nil {
+				return err
+			}
+
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nThe %s workspace has been started at %s!\n", cliui.Styles.Keyword.Render(workspace.Name), cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
+			return nil
 		},
 	}
 	cliui.AllowSkipPrompt(cmd)
@@ -1,6 +1,7 @@
 package cli

 import (
+	"fmt"
 	"io"
 	"os"
 	"time"
@@ -26,7 +27,7 @@ func statePull() *cobra.Command {
 		Use:  "pull <workspace> [file]",
 		Args: cobra.MinimumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -50,7 +51,7 @@ func statePull() *cobra.Command {
 			}

 			if len(args) < 2 {
-				cmd.Println(string(state))
+				_, _ = fmt.Fprintln(cmd.OutOrStdout(), string(state))
 				return nil
 			}

@@ -67,7 +68,7 @@ func statePush() *cobra.Command {
 		Use:  "push <workspace> <file>",
 		Args: cobra.ExactArgs(2),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -2,7 +2,6 @@ package cli_test

 import (
 	"bytes"
-	"io"
 	"os"
 	"path/filepath"
 	"strings"
@@ -97,8 +96,6 @@ func TestStatePush(t *testing.T) {
 		err = stateFile.Close()
 		require.NoError(t, err)
 		cmd, root := clitest.New(t, "state", "push", workspace.Name, stateFile.Name())
-		cmd.SetErr(io.Discard)
-		cmd.SetOut(io.Discard)
 		clitest.SetupConfig(t, client, root)
 		err = cmd.Execute()
 		require.NoError(t, err)
@@ -1,6 +1,7 @@
 package cli

 import (
+	"fmt"
 	"time"

 	"github.com/spf13/cobra"
@@ -24,7 +25,7 @@ func stop() *cobra.Command {
 				return err
 			}

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -39,7 +40,14 @@ func stop() *cobra.Command {
 			if err != nil {
 				return err
 			}
-			return cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+
+			err = cliui.WorkspaceBuild(cmd.Context(), cmd.OutOrStdout(), client, build.ID, before)
+			if err != nil {
+				return err
+			}
+
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "\nThe %s workspace has been stopped at %s!\n", cliui.Styles.Keyword.Render(workspace.Name), cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
+			return nil
 		},
 	}
 	cliui.AllowSkipPrompt(cmd)
@@ -4,7 +4,6 @@ import (
 	"fmt"
 	"os"
 	"path/filepath"
-	"sort"
 	"strings"
 	"time"

@@ -33,7 +32,7 @@ func templateCreate() *cobra.Command {
 		Short: "Create a template from the current directory or as specified by flag",
 		Args:  cobra.MaximumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -60,7 +59,7 @@ func templateCreate() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Create and upload %q?", prettyDir),
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
@@ -114,7 +113,7 @@ func templateCreate() *cobra.Command {
 			}

 			_, _ = fmt.Fprintln(cmd.OutOrStdout(), "\n"+cliui.Styles.Wrap.Render(
-				"The "+cliui.Styles.Keyword.Render(templateName)+" template has been created! "+
+				"The "+cliui.Styles.Keyword.Render(templateName)+" template has been created at "+cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp))+"! "+
 					"Developers can provision a workspace with this template using:")+"\n")

 			_, _ = fmt.Fprintln(cmd.OutOrStdout(), "  "+cliui.Styles.Code.Render(fmt.Sprintf("coder create --template=%q [workspace name]", templateName)))
@@ -127,7 +126,7 @@ func templateCreate() *cobra.Command {
 	cmd.Flags().StringVarP(&directory, "directory", "d", currentDirectory, "Specify the directory to create from")
 	cmd.Flags().StringVarP(&provisioner, "test.provisioner", "", "terraform", "Customize the provisioner backend")
 	cmd.Flags().StringVarP(&parameterFile, "parameter-file", "", "", "Specify a file path with parameter values.")
-	cmd.Flags().DurationVarP(&maxTTL, "max-ttl", "", 168*time.Hour, "Specify a maximum TTL for worksapces created from this template.")
+	cmd.Flags().DurationVarP(&maxTTL, "max-ttl", "", 24*time.Hour, "Specify a maximum TTL for workspaces created from this template.")
 	cmd.Flags().DurationVarP(&minAutostartInterval, "min-autostart-interval", "", time.Hour, "Specify a minimum autostart interval for workspaces created from this template.")
 	// This is for testing!
 	err := cmd.Flags().MarkHidden("test.provisioner")
@@ -226,10 +225,6 @@ func createValidTemplateVersion(cmd *cobra.Command, args createValidTemplateVers
 			valuesBySchemaID[parameterValue.SchemaID.String()] = parameterValue
 		}

-		sort.Slice(parameterSchemas, func(i, j int) bool {
-			return parameterSchemas[i].Name < parameterSchemas[j].Name
-		})
-
 		// parameterMapFromFile can be nil if parameter file is not specified
 		var parameterMapFromFile map[string]string
 		if args.ParameterFile != "" {
@@ -1,7 +1,6 @@
 package cli_test

 import (
-	"io"
 	"os"
 	"testing"

@@ -132,6 +131,7 @@ func TestTemplateCreate(t *testing.T) {
 			ProvisionDryRun: echo.ProvisionComplete,
 		})
 		tempDir := t.TempDir()
+		removeTmpDirUntilSuccessAfterTest(t, tempDir)
 		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
 		_, _ = parameterFile.WriteString("region: \"bananas\"")
 		cmd, root := clitest.New(t, "templates", "create", "my-template", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho), "--parameter-file", parameterFile.Name())
@@ -158,7 +158,6 @@ func TestTemplateCreate(t *testing.T) {
 		}

 		require.NoError(t, <-execDone)
-		removeTmpDirUntilSuccess(t, tempDir)
 	})

 	t.Run("WithParameterFileNotContainingTheValue", func(t *testing.T) {
@@ -171,6 +170,7 @@ func TestTemplateCreate(t *testing.T) {
 			ProvisionDryRun: echo.ProvisionComplete,
 		})
 		tempDir := t.TempDir()
+		removeTmpDirUntilSuccessAfterTest(t, tempDir)
 		parameterFile, _ := os.CreateTemp(tempDir, "testParameterFile*.yaml")
 		_, _ = parameterFile.WriteString("zone: \"bananas\"")
 		cmd, root := clitest.New(t, "templates", "create", "my-template", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho), "--parameter-file", parameterFile.Name())
@@ -196,7 +196,6 @@ func TestTemplateCreate(t *testing.T) {
 		}

 		require.EqualError(t, <-execDone, "Parameter value absent in parameter file for \"region\"!")
-		removeTmpDirUntilSuccess(t, tempDir)
 	})

 	t.Run("Recreate template with same name (create, delete, create)", func(t *testing.T) {
@@ -219,8 +218,6 @@ func TestTemplateCreate(t *testing.T) {
 			}
 			cmd, root := clitest.New(t, args...)
 			clitest.SetupConfig(t, client, root)
-			cmd.SetOut(io.Discard)
-			cmd.SetErr(io.Discard)

 			return cmd.Execute()
 		}
@@ -229,11 +226,10 @@ func TestTemplateCreate(t *testing.T) {
 				"templates",
 				"delete",
 				"my-template",
+				"--yes",
 			}
 			cmd, root := clitest.New(t, args...)
 			clitest.SetupConfig(t, client, root)
-			cmd.SetOut(io.Discard)
-			cmd.SetErr(io.Discard)

 			return cmd.Execute()
 		}
@@ -266,7 +262,7 @@ func createTestParseResponse() []*proto.Parse_Response {

 // Need this for Windows because of a known issue with Go:
 // https://github.com/golang/go/issues/52986
-func removeTmpDirUntilSuccess(t *testing.T, tempDir string) {
+func removeTmpDirUntilSuccessAfterTest(t *testing.T, tempDir string) {
 	t.Helper()
 	t.Cleanup(func() {
 		err := os.RemoveAll(tempDir)
@@ -2,6 +2,8 @@ package cli

 import (
 	"fmt"
+	"strings"
+	"time"

 	"github.com/spf13/cobra"
 	"golang.org/x/xerrors"
@@ -11,7 +13,7 @@ import (
 )

 func templateDelete() *cobra.Command {
-	return &cobra.Command{
+	cmd := &cobra.Command{
 		Use:   "delete [name...]",
 		Short: "Delete templates",
 		RunE: func(cmd *cobra.Command, args []string) error {
@@ -21,7 +23,7 @@ func templateDelete() *cobra.Command {
 				templates     = []codersdk.Template{}
 			)

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -32,6 +34,14 @@ func templateDelete() *cobra.Command {

 			if len(args) > 0 {
 				templateNames = args
+
+				for _, templateName := range templateNames {
+					template, err := client.TemplateByName(ctx, organization.ID, templateName)
+					if err != nil {
+						return xerrors.Errorf("get template by name: %w", err)
+					}
+					templates = append(templates, template)
+				}
 			} else {
 				allTemplates, err := client.TemplatesByOrganization(ctx, organization.ID)
 				if err != nil {
@@ -57,17 +67,19 @@ func templateDelete() *cobra.Command {
 				for _, template := range allTemplates {
 					if template.Name == selection {
 						templates = append(templates, template)
+						templateNames = append(templateNames, template.Name)
 					}
 				}
 			}

-			for _, templateName := range templateNames {
-				template, err := client.TemplateByName(ctx, organization.ID, templateName)
-				if err != nil {
-					return xerrors.Errorf("get template by name: %w", err)
-				}
-
-				templates = append(templates, template)
+			// Confirm deletion of the template.
+			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
+				Text:      fmt.Sprintf("Delete these templates: %s?", cliui.Styles.Code.Render(strings.Join(templateNames, ", "))),
+				IsConfirm: true,
+				Default:   cliui.ConfirmNo,
+			})
+			if err != nil {
+				return err
 			}

 			for _, template := range templates {
@@ -76,10 +88,13 @@ func templateDelete() *cobra.Command {
 					return xerrors.Errorf("delete template %q: %w", template.Name, err)
 				}

-				_, _ = fmt.Fprintln(cmd.OutOrStdout(), "Deleted template "+cliui.Styles.Code.Render(template.Name)+"!")
+				_, _ = fmt.Fprintln(cmd.OutOrStdout(), "Deleted template "+cliui.Styles.Code.Render(template.Name)+" at "+cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp))+"!")
 			}

 			return nil
 		},
 	}
+
+	cliui.AllowSkipPrompt(cmd)
+	return cmd
 }
@@ -2,11 +2,14 @@ package cli_test

 import (
 	"context"
+	"fmt"
+	"strings"
 	"testing"

 	"github.com/stretchr/testify/require"

 	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/cli/cliui"
 	"github.com/coder/coder/coderd/coderdtest"
 	"github.com/coder/coder/codersdk"
 	"github.com/coder/coder/pty/ptytest"
@@ -25,14 +28,54 @@ func TestTemplateDelete(t *testing.T) {
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)

 		cmd, root := clitest.New(t, "templates", "delete", template.Name)
+
 		clitest.SetupConfig(t, client, root)
-		require.NoError(t, cmd.Execute())
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		execDone := make(chan error)
+		go func() {
+			execDone <- cmd.Execute()
+		}()
+
+		pty.ExpectMatch(fmt.Sprintf("Delete these templates: %s?", cliui.Styles.Code.Render(template.Name)))
+		pty.WriteLine("yes")
+
+		require.NoError(t, <-execDone)

 		_, err := client.Template(context.Background(), template.ID)
 		require.Error(t, err, "template should not exist")
 	})

-	t.Run("Multiple", func(t *testing.T) {
+	t.Run("Multiple --yes", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+		templates := []codersdk.Template{
+			coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID),
+			coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID),
+			coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID),
+		}
+		templateNames := []string{}
+		for _, template := range templates {
+			templateNames = append(templateNames, template.Name)
+		}
+
+		cmd, root := clitest.New(t, append([]string{"templates", "delete", "--yes"}, templateNames...)...)
+		clitest.SetupConfig(t, client, root)
+		require.NoError(t, cmd.Execute())
+
+		for _, template := range templates {
+			_, err := client.Template(context.Background(), template.ID)
+			require.Error(t, err, "template should not exist")
+		}
+	})
+
+	t.Run("Multiple prompted", func(t *testing.T) {
 		t.Parallel()

 		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
@@ -51,7 +94,19 @@ func TestTemplateDelete(t *testing.T) {

 		cmd, root := clitest.New(t, append([]string{"templates", "delete"}, templateNames...)...)
 		clitest.SetupConfig(t, client, root)
-		require.NoError(t, cmd.Execute())
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		execDone := make(chan error)
+		go func() {
+			execDone <- cmd.Execute()
+		}()
+
+		pty.ExpectMatch(fmt.Sprintf("Delete these templates: %s?", cliui.Styles.Code.Render(strings.Join(templateNames, ", "))))
+		pty.WriteLine("yes")
+
+		require.NoError(t, <-execDone)

 		for _, template := range templates {
 			_, err := client.Template(context.Background(), template.ID)
@@ -80,7 +135,7 @@ func TestTemplateDelete(t *testing.T) {
 			execDone <- cmd.Execute()
 		}()

-		pty.WriteLine("docker-local")
+		pty.WriteLine("yes")
 		require.NoError(t, <-execDone)

 		_, err := client.Template(context.Background(), template.ID)
@@ -13,7 +13,9 @@ import (

 func templateEdit() *cobra.Command {
 	var (
+		name                 string
 		description          string
+		icon                 string
 		maxTTL               time.Duration
 		minAutostartInterval time.Duration
 	)
@@ -23,7 +25,7 @@ func templateEdit() *cobra.Command {
 		Args:  cobra.ExactArgs(1),
 		Short: "Edit the metadata of a template by name.",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return xerrors.Errorf("create client: %w", err)
 			}
@@ -38,7 +40,9 @@ func templateEdit() *cobra.Command {

 			// NOTE: coderd will ignore empty fields.
 			req := codersdk.UpdateTemplateMeta{
+				Name:                       name,
 				Description:                description,
+				Icon:                       icon,
 				MaxTTLMillis:               maxTTL.Milliseconds(),
 				MinAutostartIntervalMillis: minAutostartInterval.Milliseconds(),
 			}
@@ -47,14 +51,16 @@ func templateEdit() *cobra.Command {
 			if err != nil {
 				return xerrors.Errorf("update template metadata: %w", err)
 			}
-			_, _ = fmt.Printf("Updated template metadata!\n")
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "Updated template metadata at %s!\n", cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
 			return nil
 		},
 	}

+	cmd.Flags().StringVarP(&name, "name", "", "", "Edit the template name")
 	cmd.Flags().StringVarP(&description, "description", "", "", "Edit the template description")
-	cmd.Flags().DurationVarP(&maxTTL, "max_ttl", "", 0, "Edit the template maximum time before shutdown")
-	cmd.Flags().DurationVarP(&minAutostartInterval, "min_autostart_interval", "", 0, "Edit the template minimum autostart interval")
+	cmd.Flags().StringVarP(&icon, "icon", "", "", "Edit the template icon path")
+	cmd.Flags().DurationVarP(&maxTTL, "max-ttl", "", 0, "Edit the template maximum time before shutdown - workspaces created from this template cannot stay running longer than this.")
+	cmd.Flags().DurationVarP(&minAutostartInterval, "min-autostart-interval", "", 0, "Edit the template minimum autostart interval - workspaces created from this template must wait at least this long between autostarts.")
 	cliui.AllowSkipPrompt(cmd)

 	return cmd
@@ -25,21 +25,26 @@ func TestTemplateEdit(t *testing.T) {
 		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID, func(ctr *codersdk.CreateTemplateRequest) {
 			ctr.Description = "original description"
+			ctr.Icon = "/icons/default-icon.png"
 			ctr.MaxTTLMillis = ptr.Ref(24 * time.Hour.Milliseconds())
 			ctr.MinAutostartIntervalMillis = ptr.Ref(time.Hour.Milliseconds())
 		})

 		// Test the cli command.
+		name := "new-template-name"
 		desc := "lorem ipsum dolor sit amet et cetera"
+		icon := "/icons/new-icon.png"
 		maxTTL := 12 * time.Hour
 		minAutostartInterval := time.Minute
 		cmdArgs := []string{
 			"templates",
 			"edit",
 			template.Name,
+			"--name", name,
 			"--description", desc,
-			"--max_ttl", maxTTL.String(),
-			"--min_autostart_interval", minAutostartInterval.String(),
+			"--icon", icon,
+			"--max-ttl", maxTTL.String(),
+			"--min-autostart-interval", minAutostartInterval.String(),
 		}
 		cmd, root := clitest.New(t, cmdArgs...)
 		clitest.SetupConfig(t, client, root)
@@ -51,7 +56,9 @@ func TestTemplateEdit(t *testing.T) {
 		// Assert that the template metadata changed.
 		updated, err := client.Template(context.Background(), template.ID)
 		require.NoError(t, err)
+		assert.Equal(t, name, updated.Name)
 		assert.Equal(t, desc, updated.Description)
+		assert.Equal(t, icon, updated.Icon)
 		assert.Equal(t, maxTTL.Milliseconds(), updated.MaxTTLMillis)
 		assert.Equal(t, minAutostartInterval.Milliseconds(), updated.MinAutostartIntervalMillis)
 	})
@@ -64,6 +71,7 @@ func TestTemplateEdit(t *testing.T) {
 		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID, func(ctr *codersdk.CreateTemplateRequest) {
 			ctr.Description = "original description"
+			ctr.Icon = "/icons/default-icon.png"
 			ctr.MaxTTLMillis = ptr.Ref(24 * time.Hour.Milliseconds())
 			ctr.MinAutostartIntervalMillis = ptr.Ref(time.Hour.Milliseconds())
 		})
@@ -73,9 +81,11 @@ func TestTemplateEdit(t *testing.T) {
 			"templates",
 			"edit",
 			template.Name,
+			"--name", template.Name,
 			"--description", template.Description,
-			"--max_ttl", (time.Duration(template.MaxTTLMillis) * time.Millisecond).String(),
-			"--min_autostart_interval", (time.Duration(template.MinAutostartIntervalMillis) * time.Millisecond).String(),
+			"--icon", template.Icon,
+			"--max-ttl", (time.Duration(template.MaxTTLMillis) * time.Millisecond).String(),
+			"--min-autostart-interval", (time.Duration(template.MinAutostartIntervalMillis) * time.Millisecond).String(),
 		}
 		cmd, root := clitest.New(t, cmdArgs...)
 		clitest.SetupConfig(t, client, root)
@@ -87,7 +97,9 @@ func TestTemplateEdit(t *testing.T) {
 		// Assert that the template metadata did not change.
 		updated, err := client.Template(context.Background(), template.ID)
 		require.NoError(t, err)
+		assert.Equal(t, template.Name, updated.Name)
 		assert.Equal(t, template.Description, updated.Description)
+		assert.Equal(t, template.Icon, updated.Icon)
 		assert.Equal(t, template.MaxTTLMillis, updated.MaxTTLMillis)
 		assert.Equal(t, template.MinAutostartIntervalMillis, updated.MinAutostartIntervalMillis)
 	})
@@ -25,9 +25,10 @@ func templateInit() *cobra.Command {
 			exampleByName := map[string]examples.Example{}
 			for _, example := range exampleList {
 				name := fmt.Sprintf(
-					"%s\n%s\n",
+					"%s\n%s\n%s\n",
 					cliui.Styles.Bold.Render(example.Name),
 					cliui.Styles.Wrap.Copy().PaddingLeft(6).Render(example.Description),
+					cliui.Styles.Keyword.Copy().PaddingLeft(6).Render(example.URL),
 				)
 				exampleNames = append(exampleNames, name)
 				exampleByName[name] = example
@@ -35,7 +36,7 @@ func templateInit() *cobra.Command {

 			_, _ = fmt.Fprintln(cmd.OutOrStdout(), cliui.Styles.Wrap.Render(
 				"A template defines infrastructure as code to be provisioned "+
-					"for individual developer workspaces. Select an example to get started:\n"))
+					"for individual developer workspaces. Select an example to be copied to the active directory:\n"))
 			option, err := cliui.Select(cmd, cliui.SelectOptions{
 				Options: exampleNames,
 			})
@@ -13,9 +13,10 @@ func templateList() *cobra.Command {
 	)
 	cmd := &cobra.Command{
 		Use:     "list",
+		Short:   "List all the templates available for the organization",
 		Aliases: []string{"ls"},
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -29,12 +30,17 @@ func templateList() *cobra.Command {
 			}

 			if len(templates) == 0 {
-				_, _ = fmt.Fprintf(cmd.OutOrStdout(), "%s No templates found in %s! Create one:\n\n", caret, color.HiWhiteString(organization.Name))
-				_, _ = fmt.Fprintln(cmd.OutOrStdout(), color.HiMagentaString("  $ coder templates create <directory>\n"))
+				_, _ = fmt.Fprintf(cmd.ErrOrStderr(), "%s No templates found in %s! Create one:\n\n", caret, color.HiWhiteString(organization.Name))
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), color.HiMagentaString("  $ coder templates create <directory>\n"))
 				return nil
 			}

-			_, err = fmt.Fprintln(cmd.OutOrStdout(), displayTemplates(columns, templates...))
+			out, err := displayTemplates(columns, templates...)
+			if err != nil {
+				return err
+			}
+
+			_, err = fmt.Fprintln(cmd.OutOrStdout(), out)
 			return err
 		},
 	}
@@ -0,0 +1,71 @@
+package cli_test
+
+import (
+	"sort"
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/pty/ptytest"
+)
+
+func TestTemplateList(t *testing.T) {
+	t.Parallel()
+	t.Run("ListTemplates", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		firstVersion := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, firstVersion.ID)
+		firstTemplate := coderdtest.CreateTemplate(t, client, user.OrganizationID, firstVersion.ID)
+
+		secondVersion := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, secondVersion.ID)
+		secondTemplate := coderdtest.CreateTemplate(t, client, user.OrganizationID, secondVersion.ID)
+
+		cmd, root := clitest.New(t, "templates", "list")
+		clitest.SetupConfig(t, client, root)
+
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		errC := make(chan error)
+		go func() {
+			errC <- cmd.Execute()
+		}()
+
+		// expect that templates are listed alphebetically
+		var templatesList = []string{firstTemplate.Name, secondTemplate.Name}
+		sort.Strings(templatesList)
+
+		require.NoError(t, <-errC)
+
+		for _, name := range templatesList {
+			pty.ExpectMatch(name)
+		}
+	})
+	t.Run("NoTemplates", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		coderdtest.CreateFirstUser(t, client)
+
+		cmd, root := clitest.New(t, "templates", "list")
+		clitest.SetupConfig(t, client, root)
+
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetErr(pty.Output())
+
+		errC := make(chan error)
+		go func() {
+			errC <- cmd.Execute()
+		}()
+
+		require.NoError(t, <-errC)
+
+		pty.ExpectMatch("No templates found in testuser! Create one:")
+	})
+}
@@ -8,7 +8,7 @@ func templatePlan() *cobra.Command {
 	return &cobra.Command{
 		Use:   "plan <directory>",
 		Args:  cobra.MinimumNArgs(1),
-		Short: "Plan a template update from the current directory",
+		Short: "Plan a template push from the current directory",
 		RunE: func(cmd *cobra.Command, args []string) error {
 			return nil
 		},
@@ -17,7 +17,7 @@ func templatePull() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "pull <name> [destination]",
 		Short: "Download the latest version of a template to a path.",
-		Args:  cobra.MaximumNArgs(2),
+		Args:  cobra.RangeArgs(1, 2),
 		RunE: func(cmd *cobra.Command, args []string) error {
 			var (
 				ctx          = cmd.Context()
@@ -29,7 +29,7 @@ func templatePull() *cobra.Command {
 				dest = args[1]
 			}

-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return xerrors.Errorf("create client: %w", err)
 			}
@@ -19,6 +19,14 @@ import (
 func TestTemplatePull(t *testing.T) {
 	t.Parallel()

+	t.Run("NoName", func(t *testing.T) {
+		t.Parallel()
+
+		cmd, _ := clitest.New(t, "templates", "pull")
+		err := cmd.Execute()
+		require.Error(t, err)
+	})
+
 	// Stdout tests that 'templates pull' pulls down the latest template
 	// and writes it to stdout.
 	t.Run("Stdout", func(t *testing.T) {
@@ -3,6 +3,7 @@ package cli
 import (
 	"fmt"
 	"os"
+	"path/filepath"
 	"time"

 	"github.com/briandowns/spinner"
@@ -15,7 +16,7 @@ import (
 	"github.com/coder/coder/provisionersdk"
 )

-func templateUpdate() *cobra.Command {
+func templatePush() *cobra.Command {
 	var (
 		directory     string
 		provisioner   string
@@ -24,11 +25,11 @@ func templateUpdate() *cobra.Command {
 	)

 	cmd := &cobra.Command{
-		Use:   "update <template>",
-		Args:  cobra.ExactArgs(1),
-		Short: "Update the source-code of a template from the current directory or as specified by flag",
+		Use:   "push [template]",
+		Args:  cobra.MaximumNArgs(1),
+		Short: "Push a new template version from the current directory or as specified by flag",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -36,7 +37,13 @@ func templateUpdate() *cobra.Command {
 			if err != nil {
 				return err
 			}
-			template, err := client.TemplateByName(cmd.Context(), organization.ID, args[0])
+
+			name := filepath.Base(directory)
+			if len(args) > 0 {
+				name = args[0]
+			}
+
+			template, err := client.TemplateByName(cmd.Context(), organization.ID, name)
 			if err != nil {
 				return err
 			}
@@ -46,7 +53,7 @@ func templateUpdate() *cobra.Command {
 			_, err = cliui.Prompt(cmd, cliui.PromptOptions{
 				Text:      fmt.Sprintf("Upload %q?", prettyDir),
 				IsConfirm: true,
-				Default:   "yes",
+				Default:   cliui.ConfirmYes,
 			})
 			if err != nil {
 				return err
@@ -91,7 +98,7 @@ func templateUpdate() *cobra.Command {
 				return err
 			}

-			_, _ = fmt.Printf("Updated version!\n")
+			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "Updated version at %s!\n", cliui.Styles.DateTimeStamp.Render(time.Now().Format(time.Stamp)))
 			return nil
 		},
 	}
@@ -2,6 +2,7 @@ package cli_test

 import (
 	"context"
+	"path/filepath"
 	"testing"

 	"github.com/google/uuid"
@@ -16,7 +17,7 @@ import (
 	"github.com/coder/coder/pty/ptytest"
 )

-func TestTemplateUpdate(t *testing.T) {
+func TestTemplatePush(t *testing.T) {
 	t.Parallel()
 	// NewParameter will:
 	//	1. Create a template version with 0 params
@@ -42,7 +43,7 @@ func TestTemplateUpdate(t *testing.T) {
 			Parse:     createTestParseResponse(),
 			Provision: echo.ProvisionComplete,
 		})
-		cmd, root := clitest.New(t, "templates", "update", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
+		cmd, root := clitest.New(t, "templates", "push", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
 		clitest.SetupConfig(t, client, root)
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
@@ -75,7 +76,7 @@ func TestTemplateUpdate(t *testing.T) {

 		// Second update of the same source requires no prompt since the params
 		// are carried over.
-		cmd, root = clitest.New(t, "templates", "update", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
+		cmd, root = clitest.New(t, "templates", "push", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
 		clitest.SetupConfig(t, client, root)
 		go func() {
 			execDone <- cmd.Execute()
@@ -94,7 +95,7 @@ func TestTemplateUpdate(t *testing.T) {
 			Provision: echo.ProvisionComplete,
 		})

-		cmd, root = clitest.New(t, "templates", "update", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
+		cmd, root = clitest.New(t, "templates", "push", template.Name, "-y", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
 		clitest.SetupConfig(t, client, root)
 		go func() {
 			execDone <- cmd.Execute()
@@ -113,6 +114,7 @@ func TestTemplateUpdate(t *testing.T) {
 		user := coderdtest.CreateFirstUser(t, client)
 		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
 		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+
 		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)

 		// Test the cli command.
@@ -120,7 +122,60 @@ func TestTemplateUpdate(t *testing.T) {
 			Parse:     echo.ParseComplete,
 			Provision: echo.ProvisionComplete,
 		})
-		cmd, root := clitest.New(t, "templates", "update", template.Name, "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
+		cmd, root := clitest.New(t, "templates", "push", template.Name, "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
+		clitest.SetupConfig(t, client, root)
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		execDone := make(chan error)
+		go func() {
+			execDone <- cmd.Execute()
+		}()
+
+		matches := []struct {
+			match string
+			write string
+		}{
+			{match: "Upload", write: "yes"},
+		}
+		for _, m := range matches {
+			pty.ExpectMatch(m.match)
+			pty.WriteLine(m.write)
+		}
+
+		require.NoError(t, <-execDone)
+
+		// Assert that the template version changed.
+		templateVersions, err := client.TemplateVersionsByTemplate(context.Background(), codersdk.TemplateVersionsByTemplateRequest{
+			TemplateID: template.ID,
+		})
+		require.NoError(t, err)
+		assert.Len(t, templateVersions, 2)
+		assert.NotEqual(t, template.ActiveVersionID, templateVersions[1].ID)
+	})
+
+	t.Run("UseWorkingDir", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+
+		// Test the cli command.
+		source := clitest.CreateTemplateVersionSource(t, &echo.Responses{
+			Parse:     echo.ParseComplete,
+			Provision: echo.ProvisionComplete,
+		})
+
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID,
+			func(r *codersdk.CreateTemplateRequest) {
+				r.Name = filepath.Base(source)
+			})
+
+		// Don't pass the name of the template, it should use the
+		// directory of the source.
+		cmd, root := clitest.New(t, "templates", "push", "--directory", source, "--test.provisioner", string(database.ProvisionerTypeEcho))
 		clitest.SetupConfig(t, client, root)
 		pty := ptytest.New(t)
 		cmd.SetIn(pty.Input())
@@ -4,7 +4,7 @@ import (
 	"fmt"
 	"time"

-	"github.com/jedib0t/go-pretty/v6/table"
+	"github.com/google/uuid"
 	"github.com/spf13/cobra"

 	"github.com/coder/coder/cli/cliui"
@@ -16,18 +16,20 @@ func templates() *cobra.Command {
 		Use:     "templates",
 		Short:   "Create, manage, and deploy templates",
 		Aliases: []string{"template"},
-		Example: `
-  - Create a template for developers to create workspaces
-
-    ` + cliui.Styles.Code.Render("$ coder templates create") + `
-
-  - Make changes to your template, and plan the changes
-
-    ` + cliui.Styles.Code.Render("$ coder templates plan <name>") + `
-
-  - Update the template. Your developers can update their workspaces
-
-    ` + cliui.Styles.Code.Render("$ coder templates update <name>"),
+		Example: formatExamples(
+			example{
+				Description: "Create a template for developers to create workspaces",
+				Command:     "coder templates create",
+			},
+			example{
+				Description: "Make changes to your template, and plan the changes",
+				Command:     "coder templates plan my-template",
+			},
+			example{
+				Description: "Push an update to the template. Your developers can update their workspaces",
+				Command:     "coder templates push my-template",
+			},
+		),
 	}
 	cmd.AddCommand(
 		templateCreate(),
@@ -35,7 +37,7 @@ func templates() *cobra.Command {
 		templateInit(),
 		templateList(),
 		templatePlan(),
-		templateUpdate(),
+		templatePush(),
 		templateVersions(),
 		templateDelete(),
 		templatePull(),
@@ -44,35 +46,41 @@ func templates() *cobra.Command {
 	return cmd
 }

+type templateTableRow struct {
+	Name                 string                   `table:"name"`
+	CreatedAt            string                   `table:"created at"`
+	LastUpdated          string                   `table:"last updated"`
+	OrganizationID       uuid.UUID                `table:"organization id"`
+	Provisioner          codersdk.ProvisionerType `table:"provisioner"`
+	ActiveVersionID      uuid.UUID                `table:"active version id"`
+	UsedBy               string                   `table:"used by"`
+	MaxTTL               time.Duration            `table:"max ttl"`
+	MinAutostartInterval time.Duration            `table:"min autostart"`
+}
+
 // displayTemplates will return a table displaying all templates passed in.
 // filterColumns must be a subset of the template fields and will determine which
 // columns to display
-func displayTemplates(filterColumns []string, templates ...codersdk.Template) string {
-	tableWriter := cliui.Table()
-	header := table.Row{
-		"Name", "Created At", "Last Updated", "Organization ID", "Provisioner",
-		"Active Version ID", "Used By", "Max TTL", "Min Autostart"}
-	tableWriter.AppendHeader(header)
-	tableWriter.SetColumnConfigs(cliui.FilterTableColumns(header, filterColumns))
-	tableWriter.SortBy([]table.SortBy{{
-		Name: "name",
-	}})
-	for _, template := range templates {
+func displayTemplates(filterColumns []string, templates ...codersdk.Template) (string, error) {
+	rows := make([]templateTableRow, len(templates))
+	for i, template := range templates {
 		suffix := ""
 		if template.WorkspaceOwnerCount != 1 {
 			suffix = "s"
 		}
-		tableWriter.AppendRow(table.Row{
-			template.Name,
-			template.CreatedAt.Format("January 2, 2006"),
-			template.UpdatedAt.Format("January 2, 2006"),
-			template.OrganizationID.String(),
-			template.Provisioner,
-			template.ActiveVersionID.String(),
-			cliui.Styles.Fuschia.Render(fmt.Sprintf("%d developer%s", template.WorkspaceOwnerCount, suffix)),
-			(time.Duration(template.MaxTTLMillis) * time.Millisecond).String(),
-			(time.Duration(template.MinAutostartIntervalMillis) * time.Millisecond).String(),
-		})
+
+		rows[i] = templateTableRow{
+			Name:                 template.Name,
+			CreatedAt:            template.CreatedAt.Format("January 2, 2006"),
+			LastUpdated:          template.UpdatedAt.Format("January 2, 2006"),
+			OrganizationID:       template.OrganizationID,
+			Provisioner:          template.Provisioner,
+			ActiveVersionID:      template.ActiveVersionID,
+			UsedBy:               cliui.Styles.Fuchsia.Render(fmt.Sprintf("%d developer%s", template.WorkspaceOwnerCount, suffix)),
+			MaxTTL:               (time.Duration(template.MaxTTLMillis) * time.Millisecond),
+			MinAutostartInterval: (time.Duration(template.MinAutostartIntervalMillis) * time.Millisecond),
+		}
 	}
-	return tableWriter.Render()
+
+	return cliui.DisplayTable(rows, "name", filterColumns)
 }
@@ -1,15 +1,101 @@
 package cli

-import "github.com/spf13/cobra"
+import (
+	"fmt"
+	"strings"
+	"time"
+
+	"github.com/google/uuid"
+	"github.com/spf13/cobra"
+	"golang.org/x/xerrors"
+
+	"github.com/coder/coder/cli/cliui"
+	"github.com/coder/coder/codersdk"
+)

 func templateVersions() *cobra.Command {
-	return &cobra.Command{
+	cmd := &cobra.Command{
 		Use:     "versions",
+		Short:   "Manage different versions of the specified template",
 		Aliases: []string{"version"},
+		Example: formatExamples(
+			example{
+				Description: "List versions of a specific template",
+				Command:     "coder templates versions list my-template",
+			},
+		),
+	}
+	cmd.AddCommand(
+		templateVersionsList(),
+	)
+
+	return cmd
+}
+
+func templateVersionsList() *cobra.Command {
+	return &cobra.Command{
+		Use:   "list <template>",
+		Args:  cobra.ExactArgs(1),
+		Short: "List all the versions of the specified template",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			return nil
+			client, err := CreateClient(cmd)
+			if err != nil {
+				return xerrors.Errorf("create client: %w", err)
+			}
+			organization, err := currentOrganization(cmd, client)
+			if err != nil {
+				return xerrors.Errorf("get current organization: %w", err)
+			}
+			template, err := client.TemplateByName(cmd.Context(), organization.ID, args[0])
+			if err != nil {
+				return xerrors.Errorf("get template by name: %w", err)
+			}
+			req := codersdk.TemplateVersionsByTemplateRequest{
+				TemplateID: template.ID,
+			}
+
+			versions, err := client.TemplateVersionsByTemplate(cmd.Context(), req)
+			if err != nil {
+				return xerrors.Errorf("get template versions by template: %w", err)
+			}
+
+			out, err := displayTemplateVersions(template.ActiveVersionID, versions...)
+			if err != nil {
+				return xerrors.Errorf("render table: %w", err)
+			}
+
+			_, err = fmt.Fprintln(cmd.OutOrStdout(), out)
+			return err
 		},
 	}
 }

-// coder template versions
+type templateVersionRow struct {
+	Name      string    `table:"name"`
+	CreatedAt time.Time `table:"created at"`
+	CreatedBy string    `table:"created by"`
+	Status    string    `table:"status"`
+	Active    string    `table:"active"`
+}
+
+// displayTemplateVersions will return a table displaying existing
+// template versions for the specified template.
+func displayTemplateVersions(activeVersionID uuid.UUID, templateVersions ...codersdk.TemplateVersion) (string, error) {
+	rows := make([]templateVersionRow, len(templateVersions))
+	for i, templateVersion := range templateVersions {
+		var activeStatus = ""
+		if templateVersion.ID == activeVersionID {
+			activeStatus = cliui.Styles.Code.Render(cliui.Styles.Keyword.Render("Active"))
+		}
+
+		rows[i] = templateVersionRow{
+			Name:      templateVersion.Name,
+			CreatedAt: templateVersion.CreatedAt,
+			CreatedBy: templateVersion.CreatedByName,
+			Status:    strings.Title(string(templateVersion.Job.Status)),
+			Active:    activeStatus,
+		}
+	}
+
+	return cliui.DisplayTable(rows, "name", nil)
+}
@@ -0,0 +1,41 @@
+package cli_test
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/pty/ptytest"
+)
+
+func TestTemplateVersions(t *testing.T) {
+	t.Parallel()
+	t.Run("ListVersions", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		version := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, version.ID)
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version.ID)
+
+		cmd, root := clitest.New(t, "templates", "versions", "list", template.Name)
+		clitest.SetupConfig(t, client, root)
+
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		errC := make(chan error)
+		go func() {
+			errC <- cmd.Execute()
+		}()
+
+		require.NoError(t, <-errC)
+
+		pty.ExpectMatch(version.Name)
+		pty.ExpectMatch(version.CreatedByName)
+		pty.ExpectMatch("Active")
+	})
+}
@@ -6,16 +6,23 @@ import (

 	"github.com/spf13/cobra"

+	"github.com/coder/coder/cli/cliflag"
 	"github.com/coder/coder/codersdk"
 )

 func update() *cobra.Command {
-	return &cobra.Command{
+	var (
+		parameterFile string
+		alwaysPrompt  bool
+	)
+
+	cmd := &cobra.Command{
 		Annotations: workspaceCommand,
-		Use:         "update",
+		Use:         "update <workspace>",
+		Args:        cobra.ExactArgs(1),
 		Short:       "Update a workspace to the latest template version",
 		RunE: func(cmd *cobra.Command, args []string) error {
-			client, err := createClient(cmd)
+			client, err := CreateClient(cmd)
 			if err != nil {
 				return err
 			}
@@ -23,18 +30,38 @@ func update() *cobra.Command {
 			if err != nil {
 				return err
 			}
-			if !workspace.Outdated {
-				_, _ = fmt.Printf("Workspace isn't outdated!\n")
+			if !workspace.Outdated && !alwaysPrompt {
+				_, _ = fmt.Fprintf(cmd.OutOrStdout(), "Workspace isn't outdated!\n")
 				return nil
 			}
 			template, err := client.Template(cmd.Context(), workspace.TemplateID)
 			if err != nil {
 				return nil
 			}
+
+			var existingParams []codersdk.Parameter
+			if !alwaysPrompt {
+				existingParams, err = client.Parameters(cmd.Context(), codersdk.ParameterWorkspace, workspace.ID)
+				if err != nil {
+					return nil
+				}
+			}
+
+			parameters, err := prepWorkspaceBuild(cmd, client, prepWorkspaceBuildArgs{
+				Template:         template,
+				ExistingParams:   existingParams,
+				ParameterFile:    parameterFile,
+				NewWorkspaceName: workspace.Name,
+			})
+			if err != nil {
+				return nil
+			}
+
 			before := time.Now()
 			build, err := client.CreateWorkspaceBuild(cmd.Context(), workspace.ID, codersdk.CreateWorkspaceBuildRequest{
 				TemplateVersionID: template.ActiveVersionID,
 				Transition:        workspace.LatestBuild.Transition,
+				ParameterValues:   parameters,
 			})
 			if err != nil {
 				return err
@@ -48,9 +75,13 @@ func update() *cobra.Command {
 				if !ok {
 					break
 				}
-				_, _ = fmt.Printf("Output: %s\n", log.Output)
+				_, _ = fmt.Fprintf(cmd.OutOrStdout(), "Output: %s\n", log.Output)
 			}
 			return nil
 		},
 	}
+
+	cmd.Flags().BoolVar(&alwaysPrompt, "always-prompt", false, "Always prompt all parameters. Does not pull parameter values from existing workspace")
+	cliflag.StringVarP(cmd.Flags(), &parameterFile, "parameter-file", "", "CODER_PARAMETER_FILE", "", "Specify a file path with parameter values.")
+	return cmd
 }
@@ -0,0 +1,141 @@
+package cli_test
+
+import (
+	"context"
+	"fmt"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/cli/clitest"
+	"github.com/coder/coder/coderd/coderdtest"
+	"github.com/coder/coder/codersdk"
+	"github.com/coder/coder/provisioner/echo"
+	"github.com/coder/coder/pty/ptytest"
+)
+
+func TestUpdate(t *testing.T) {
+	t.Parallel()
+
+	// Test that the function does not panic on missing arg.
+	t.Run("NoArgs", func(t *testing.T) {
+		t.Parallel()
+
+		cmd, _ := clitest.New(t, "update")
+		err := cmd.Execute()
+		require.Error(t, err)
+	})
+
+	t.Run("OK", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		version1 := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+
+		coderdtest.AwaitTemplateVersionJob(t, client, version1.ID)
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version1.ID)
+
+		cmd, root := clitest.New(t, "create",
+			"my-workspace",
+			"--template", template.Name,
+			"-y",
+		)
+		clitest.SetupConfig(t, client, root)
+
+		err := cmd.Execute()
+		require.NoError(t, err)
+
+		ws, err := client.WorkspaceByOwnerAndName(context.Background(), "testuser", "my-workspace", codersdk.WorkspaceOptions{})
+		require.NoError(t, err)
+		require.Equal(t, version1.ID.String(), ws.LatestBuild.TemplateVersionID.String())
+
+		version2 := coderdtest.UpdateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
+			Parse:           echo.ParseComplete,
+			Provision:       echo.ProvisionComplete,
+			ProvisionDryRun: echo.ProvisionComplete,
+		}, template.ID)
+		_ = coderdtest.AwaitTemplateVersionJob(t, client, version2.ID)
+
+		err = client.UpdateActiveTemplateVersion(context.Background(), template.ID, codersdk.UpdateActiveTemplateVersion{
+			ID: version2.ID,
+		})
+		require.NoError(t, err)
+
+		cmd, root = clitest.New(t, "update", ws.Name)
+		clitest.SetupConfig(t, client, root)
+
+		err = cmd.Execute()
+		require.NoError(t, err)
+
+		ws, err = client.WorkspaceByOwnerAndName(context.Background(), "testuser", "my-workspace", codersdk.WorkspaceOptions{})
+		require.NoError(t, err)
+		require.Equal(t, version2.ID.String(), ws.LatestBuild.TemplateVersionID.String())
+	})
+
+	t.Run("WithParameter", func(t *testing.T) {
+		t.Parallel()
+
+		client := coderdtest.New(t, &coderdtest.Options{IncludeProvisionerD: true})
+		user := coderdtest.CreateFirstUser(t, client)
+		version1 := coderdtest.CreateTemplateVersion(t, client, user.OrganizationID, nil)
+
+		coderdtest.AwaitTemplateVersionJob(t, client, version1.ID)
+		template := coderdtest.CreateTemplate(t, client, user.OrganizationID, version1.ID)
+
+		cmd, root := clitest.New(t, "create",
+			"my-workspace",
+			"--template", template.Name,
+			"-y",
+		)
+		clitest.SetupConfig(t, client, root)
+
+		err := cmd.Execute()
+		require.NoError(t, err)
+
+		ws, err := client.WorkspaceByOwnerAndName(context.Background(), "testuser", "my-workspace", codersdk.WorkspaceOptions{})
+		require.NoError(t, err)
+		require.Equal(t, version1.ID.String(), ws.LatestBuild.TemplateVersionID.String())
+
+		defaultValue := "something"
+		version2 := coderdtest.UpdateTemplateVersion(t, client, user.OrganizationID, &echo.Responses{
+			Parse:           createTestParseResponseWithDefault(defaultValue),
+			Provision:       echo.ProvisionComplete,
+			ProvisionDryRun: echo.ProvisionComplete,
+		}, template.ID)
+		coderdtest.AwaitTemplateVersionJob(t, client, version2.ID)
+
+		err = client.UpdateActiveTemplateVersion(context.Background(), template.ID, codersdk.UpdateActiveTemplateVersion{
+			ID: version2.ID,
+		})
+		require.NoError(t, err)
+
+		cmd, root = clitest.New(t, "update", ws.Name)
+		clitest.SetupConfig(t, client, root)
+
+		pty := ptytest.New(t)
+		cmd.SetIn(pty.Input())
+		cmd.SetOut(pty.Output())
+
+		doneChan := make(chan struct{})
+		go func() {
+			defer close(doneChan)
+			err := cmd.Execute()
+			assert.NoError(t, err)
+		}()
+
+		matches := []string{
+			fmt.Sprintf("Enter a value (default: %q):", defaultValue), "bingo",
+			"Enter a value:", "boingo",
+		}
+		for i := 0; i < len(matches); i += 2 {
+			match := matches[i]
+			value := matches[i+1]
+			pty.ExpectMatch(match)
+			pty.WriteLine(value)
+		}
+
+		<-doneChan
+	})
+}
--- a/Show More
+++ b/Show More