Auto-update is a claim, not a guaranteeCapability

Your install says auto-updates are enabled and hasn't attempted one in twelve days. Both are true. You're on 2.1.221; the current release is 2.1.233 — and one of the versions you skipped fixes a bug that hits your headless crons directly.

'Auto-updates: enabled' describes a mechanism, not an outcome. It means the updater is permitted to run. Whether it has run, whether it succeeded, and how far behind you are as a result are three separate questions, and the status line answers none of them. `claude doctor` reports the last attempt — yours reads 'success → 2.1.221 (2026-08-04)'. Success twelve days ago, and nothing since.

Version drift is invisible in a way that outages aren't. Nothing breaks when you skip a release; you just don't get the fixes. So the cost shows up as unexplained friction — a headless job that fails on a shadowed slash command, an MCP OAuth handshake that won't complete — and you debug it as if it were your bug, because you have no reason to suspect the version. That is expensive in exactly the way a loud failure is not.

This is the same lesson as yesterday's settings.json from the other direction. Yesterday: a mechanism you believed was protecting you had been dead for days. Today: a mechanism you believe is maintaining you hasn't run in twelve. Both were discoverable in one command. Neither was discovered, because nothing in your system asks.

Worked example

Find out where you actually are, then close the gap:

# What doctor knows about your install
claude doctor | head -12

# What's on disk — every version you've ever installed
ls ~/.local/share/claude/versions/

# Update, then verify the version actually moved
claude update
claude doctor | grep -i running

# The fix that matters to you, in 2.1.233:
#   "Fixed bundled skill aliases like /checkup and /review reporting
#    'Unknown command' in -p mode or with plugins/MCP loaded when a
#    user or project skill shadows the bundled skill"

• The doctor header carries version, install method, auto-update channel, and the date of the last attempt. Four facts, one command — worth running monthly regardless.
• The versions directory is your update history. Yours ends at 2.1.221, four entries deep. A directory that stops growing is the signal.
• `claude update` forces the attempt rather than waiting for the background trigger. Then confirm — per your own Automation Hygiene rule 1, verify the side-effect, not the trigger.
• This is why it matters rather than a nice-to-have. Shadowed skills plus -p mode is your exact configuration, named in the changelog entry.

Gotchas

• Updating mid-week can change behavior your crons depend on. Update deliberately on a day you're around to watch the next morning's plan-day run, not on a Friday night.
• A 'success' on the last attempt tells you the attempt succeeded, not that you're current. Compare the version number to the changelog, not to the word success.
• 2.1.233 also removed todo/task tools by default on newer models (set CLAUDE_CODE_ENABLE_TODO_TOOLS=1 to restore). If any skill of yours leans on TodoWrite, that's a behavior change to expect.