Add inline auto-update prompt after version notification

[gtrrz-victor]

https://entire.io/gh/entireio/cli/trails/e09fcff9bd93

Example

On error:

$ env ENTIRE_VERSION_CHECK_URL=http://localhost:8765/release.json ENTIRE_VERSION_CHECK_INSTALL_CMD='brew upgrade --cask entire-error' /tmp/entire-old version

Entire CLI 0.1.0 (unknown)
Go version: go1.26.2
OS/Arch: darwin/arm64

A newer version of Entire CLI is available: v99.0.0 (current: 0.1.0)

Updating Entire CLI: brew upgrade --cask entire-error
Error: Cask 'entire-error' is unavailable: No Cask with this name exists.
Update failed: installer exited: exit status 1
Try again later running:
  brew upgrade --cask entire-error

Flow

flowchart TD
  start(["entire <command>"]) --> dev{"version == 'dev' or empty?"}
  dev -- yes --> skip(["silent exit<br/>(no cache touched)"])
  dev -- no --> cache{"cache age &lt; 24h?"}
  cache -- yes --> skip
  cache -- no --> fetch["fetch GitHub /releases/latest<br/>(2s timeout)"]
  fetch --> bump["cache.LastCheckTime := now()<br/>saveCache()"]
  bump --> fok{fetch succeeded?}
  fok -- no --> done24
  fok -- yes --> outdated{isOutdated?}
  outdated -- no --> done24
  outdated -- yes --> banner["print banner:<br/>'A newer version of Entire CLI is available: vX (current: vY)'"]
  banner --> autoOK{"canAutoInstall()<br/>(Windows + scoop/mise OK;<br/>Windows + unknown blocked)"}
  autoOK -- "false<br/>(Windows + unknown installer)" --> winHint["print download hint:<br/>'To update, download the latest release from:'<br/>'  https://github.com/entireio/cli/releases'"]
  winHint --> done24
  autoOK -- true --> kill{"ENTIRE_NO_AUTO_UPDATE set?"}
  kill -- yes --> hint["print manual hint:<br/>'To update, run:'<br/>'  &lt;installer cmd&gt;'"]
  kill -- no --> tty{"CanPromptInteractively()<br/>&amp;&amp; isTerminalOut(stdout)"}
  tty -- "false<br/>(CI=true, no /dev/tty,<br/>agent subprocess, redirected stdout)" --> hint
  tty -- true --> prompt["huh prompt:<br/>'Install the new version now?'"]
  hint --> done24
  prompt --> ans{user answer}
  ans -- No --> done24
  ans -- Yes --> run["run installer command<br/>(brew / mise / scoop / curl)"]
  run --> res{installer exit code}
  res -- 0 --> ok["print:<br/>'Update complete. Re-run entire to use the new version.'"]
  res -- "non-zero" --> fail["print:<br/>'Update failed: &lt;err&gt;'<br/>'Try again later running:'<br/>'  &lt;installer cmd&gt;'"]
  ok --> done24
  fail --> done24
  done24(["24h cache is fresh<br/>no re-prompt until it expires"])

Loading

Invariants:

• Every path that reaches the fetch step bumps the 24h cache — declining, a failed fetch, a "not outdated" result, a no-TTY exit, a Windows-unknown exit, and a failed installer all look the same to the cache. The only way to re-prompt sooner is to delete ~/.config/entire/version_check.json or wait 24h.
• Dev builds (version == "dev") and invocations with a fresh cache short-circuit before ever touching the GitHub API.
• The interactive prompt has three guardrails in front of it: canAutoInstall() (blocks Windows when no known install manager is detected, since the POSIX curl-pipe-bash fallback would fail from cmd.exe), the ENTIRE_NO_AUTO_UPDATE kill switch, and the combined CanPromptInteractively() && isTerminalOut(stdout) gate. The kill switch and interactive gates both print To update, run: <cmd>; the Windows-unknown path prints a download link instead (no POSIX command is surfaced on Windows).

Summary

• When the existing daily version check flags an outdated release, the CLI prints the usual notification and then asks "Install the new version now? [Y/n]".
• Accepting runs whatever command versioncheck.updateCommand(current) resolves to (brew upgrade --cask entire[@nightly], mise upgrade entire, scoop update entire/cli, or the curl-pipe-bash fallback). stdin/stdout/stderr stream through so installer prompts and progress reach the user.
• Declining or a failed installer both leave the 24h cache in place — the user is not re-prompted for 24h in either case. If the installer command fails, a retry hint ("Try again later running: <installer command>") is printed so the user can run it manually once the upstream issue is fixed, without being nagged every invocation.
• Guardrails: stdout must be a TTY (both CanPromptInteractively() and isTerminalOut(w) must be true, so redirected output skips the prompt), CI must be empty or false, ENTIRE_NO_AUTO_UPDATE=1 is a kill switch, and on Windows the auto-run is blocked unless scoop or mise was detected (no POSIX curl-pipe-bash executed from cmd.exe).

Test plan

• mise run check green locally (unit + integration + canary)
• Unit: TTY gate, CI gate (CI=true blocks, CI=false overrides), kill-switch, user-declines, happy path, installer failure with retry hint, installer-failure keeps 24h cache fresh, kill-switch / no-TTY / CI paths all print manual-update hint, non-terminal writer skips prompt, Windows + unknown installer shows download link without auto-running, Windows + scoop still auto-runs
• Manual end-to-end on a real outdated brew install (reviewer)
• Windows scoop path verification (deferred)

Non-goals

• No silent auto-install mode — prompt is always interactive.
• No persisted preference / subcommands — kill-switch env is the escape hatch.
• No self-built binary download; shells out to the native installer.

See docs/architecture/auto-update.md.

Replaces #981 (clean history — single commit on top of main with only the auto-update files).

🤖 Generated with Claude Code

---

Note

Medium Risk
Introduces a new interactive prompt and executes installer commands via sh -c/cmd /C, which could affect UX or fail in edge environments; guardrails and tests reduce but don’t eliminate runtime risk.

Overview
When the daily version check detects the CLI is outdated, it now follows the existing notification with an interactive Y/N prompt to install the new version, and on confirmation shells out to the resolved installer command (brew/mise/scoop/curl), streaming stdin/stdout/stderr so prompts and progress are visible.

The prompt is skipped silently when non-interactive (no TTY) or when ENTIRE_NO_AUTO_UPDATE is set, and failures are non-blocking (debug-logged or printed as a simple update failure message). Adds unit tests for the auto-update flow and documents the behavior in docs/architecture/auto-update.md.

^{Reviewed by Cursor Bugbot for commit 5872166. Configure here.}

Update Since Original Description

• Added a redirected-output guard to the auto-update path so the prompt is only shown when prompting is allowed and the command's output writer is terminal-backed.
• Commands such as entire status > out.txt now skip the interactive confirm and print the manual update command instead of opening a prompt on /dev/tty.
• Added unit coverage for the non-terminal writer case and adjusted the existing CheckAndNotify test seam so terminal vs redirected-output behavior is exercised explicitly.

Additional Verification

• mise run lint
• go test ./cmd/entire/cli/versioncheck

Remaining Follow-Up

• The Windows fallback installer path still resolves to the POSIX curl -fsSL https://entire.io/install.sh | bash command for unknown install methods, so that path should not be auto-executed on Windows until it has a Windows-safe fallback. Resolved in d20d773: canAutoInstall() now returns false on Windows when the install manager is unknown, skipping the prompt and printing a download-page link instead.

[Copilot]

Pull request overview

Adds an interactive inline auto-update flow to the existing daily version check so that, when an outdated release is detected, the CLI can optionally run the appropriate installer command (brew/mise/scoop/curl) immediately.

Changes:

• Invoke a new MaybeAutoUpdate prompt after printing the “newer version available” notification.
• Add the auto-update implementation that prompts the user and shells out to the resolved installer command with stdio passthrough.
• Add unit tests and architecture documentation for the new behavior.

Reviewed changes

Copilot reviewed 5 out of 5 changed files in this pull request and generated 1 comment.

Show a summary per file

File	Description
docs/architecture/auto-update.md	Documents the new post-notification auto-update prompt and its guardrails.
cmd/entire/cli/versioncheck/versioncheck.go	Calls MaybeAutoUpdate after printing the outdated-version notification; minor comment tweaks.
cmd/entire/cli/versioncheck/autoupdate.go	Implements interactive confirm prompt + installer subprocess execution.
cmd/entire/cli/versioncheck/autoupdate_test.go	Adds unit tests covering guardrails, decline path, success, and installer failure messaging.
cmd/entire/cli/versioncheck/versioncheck_test.go	Minor refactor in TestUpdateCommand (path constant reuse).

[gtrrz-victor]

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