A checkpoint is a short progress note on a running focus — extension and Sidecar both support them; only the phone can currently hear you say one.
Open the checkpoint prompt from the InBar, the FocusBar, or the sidebar — it asks "What have you accomplished since your last checkpoint?", then "Submit with progress level:" — choose 😐 None, 📈 Little, 🚀 A Lot, 🏁 Almost Done, or 🚧 Stuck. If the InBar nudges you first, you can also ⏰ Snooze 5 min or Skip this time.
The 📋 Checkpoint toggle on the Focus tab opens What have you done since the last checkpoint? (with a mic button) and the same five-level picker: 😐 None, 📈 Little, 🚀 A lot, 🏁 Almost, 🚧 Stuck.
Tap the mic next to any text field — setting a focus, adding a checkpoint — and it fills the field from what you say.
Settings → "Voice check-ins" card → "Proactive spoken check-ins" (off by default).
Go quiet mid-focus and Tabby asks out loud, "How's {focus} going?" Tap 🎙 Check in to answer any time, or just respond when it asks — try "extend 10 minutes," "pause," "resume," "done," or just describe your progress.
What you say applies with a visible confirmation strip (e.g. "✓ Paused") and an Undo link — extends don't get Undo; use ✏️ Update focus instead if one was wrong.
Shared with nudges — Settings → "Work schedule & nudges" → Quiet hours start / end.
Settings → "Chaperone voice" → "Personality interrupts", with its own quiet hours (Off / 10pm–8am / 9pm–9am). This is what speaks a nudge on a paired Context View screen if you wander off — see Phone Focus Mode & the red screen.