calendar-cleanup

name	calendar-cleanup
description	Sweep Wolf calendars and the DMP calendar for OoO mirroring, tag-line normalization, and DMP conflict detection. Auto mode is silent and runs once per day, fired by the first worklog-touching skill that creates today's worklog file. Interactive mode (default) does the full sweep.
argument-hint	[--auto]
allowed-tools	Read, Write, Edit, AskUserQuestion, mcp__apple-events__calendar_events, mcp__apple-events__calendar_calendars

Calendar Cleanup

Periodic maintenance sweep across personal (Wolf (Shared), Wolf (Private)) and DMP (Calendar) calendars.

Two modes, depending on argument:

• --auto: Silent run. Mirrors out-of-office events to the DMP calendar. Surfaces a one-line summary of conflicts. No prompts. No tag work.
• No argument (interactive): Full sweep — Pass 1 OoO mirroring + Pass 2 tag normalization (with prompts) + Pass 3 conflict resolution (with prompts).

The skill runs automatically once per day, fired by whichever worklog-touching skill first creates today's worklog file. It can also be invoked manually at any time.

Calendars

• Wolf calendars — Wolf (Shared) and Wolf (Private). Personal events.
• DMP calendar — named exactly Calendar (M365). Work calendar.
• Wolf OoO mirror — events titled exactly Wolf OoO on Calendar. Created and managed by this skill.
• Wolf PTO block — events titled exactly Wolf PTO on Calendar. Created manually by Wolf to mark approved PTO days. Recognized but not created by this skill.

Lookahead window

All passes scan events from today through 14 days ahead.

Argument parsing

If $ARGUMENTS contains the literal token --auto, run in auto mode. Otherwise run in interactive mode.

Procedure

1. Determine mode from $ARGUMENTS.
2. Read events on Wolf (Shared) and Wolf (Private) for the lookahead window. Combine into one source list.
3. Read events on Calendar for the same window. Separate into three lists: Wolf OoO mirrors (title equals Wolf OoO), Wolf PTO blocks (title equals Wolf PTO), and DMP events (everything else).
4. Run Pass 1 — OoO mirroring (always).
5. If interactive, run Pass 2 — Tag-line normalization.
6. Run Pass 3 — Conflict detection:
   • Auto: emit single-line summary, end.
   • Interactive: walk through conflicts with the user.
7. Emit a final summary line on completion.

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Pass 1 — OoO mirroring (both modes; silent)

For each Wolf-calendar event whose [startDate, endDate] intersects ANY 8 AM – 5 PM Mon–Fri window:

1. Weekend exclusion: If the event's start date falls on a Saturday or Sunday → skip. Do not create OoO mirrors for weekend events.
2. Free all-day exclusion: If the event is all-day and has availability: free → skip. All-day free events are informational markers or planned days off where Wolf is simply not working — no OoO mirror is needed because there is no work to interrupt.
3. PTO suppression: Check if the event's start date falls within any Wolf PTO block's date range. If yes → skip (the PTO block already marks Wolf as absent; an OoO mirror would be redundant noise).
4. Look up the Wolf OoO mirror list (Step 3 above) for an event whose start and end exactly match the source event's window.
5. If a matching mirror exists → skip.
6. Otherwise, create on Calendar via mcp__apple-events__calendar_events (action: create):
   • targetCalendar: Calendar
   • title: Wolf OoO
   • startDate / endDate: the full source-event window — do NOT clip to 8–5
   • availability: unavailable (renders as Out of Office in M365)
   • Omit note, location, url, attendees, alarms — no detail leaks.

Intersection rule: any overlap with work hours triggers a mirror, even partial. Example: a 7:30–8:15 personal event mirrors as a 7:30–8:15 OoO event because the 8:00–8:15 segment intersects work hours.

Recurring source events: in v1, mirror only the specific instances that fall in the lookahead window. Do NOT propagate recurrence rules to the mirror — each daily auto-run catches newly-entered instances.

Track count of mirrors created for the final summary.

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Pass 2 — Tag-line normalization (interactive only)

For each event on the Wolf calendars in the lookahead window:

1. Read the event's current note.
2. Inspect the first non-empty line.
3. If that line consists solely of whitespace-separated #tag tokens, the event is already normalized — skip silently.
4. Otherwise, infer candidate tags from the event title and any existing note content against the tag taxonomy.
5. Use AskUserQuestion to present:
   • Event title and time window
   • Current note (or (empty))
   • Proposed tag line
   • Choices: Accept, Edit (user types replacement tag line), Skip, Extend taxonomy (user adds a new tag to the canonical list for the rest of this session)
6. On Accept or Edit, update the event's note: prepend the chosen tag line + a blank line to the existing note string, then update via mcp__apple-events__calendar_events (action: update).

Track count of tag lines added for the final summary.

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Pass 3 — Conflict detection

For each Wolf-calendar event on a weekday (Mon–Fri) whose window intersects work hours (8 AM – 5 PM):

1. From the DMP-events list (Step 3 of Procedure), find any whose time window overlaps the Wolf event's window.
2. These are conflicts.

Auto mode

Count conflicts across all Wolf events. Emit one summary line:

• If conflicts == 0: Calendar cleanup: OoO mirrors synced (N created); no conflicts.
• If conflicts > 0: Calendar cleanup: OoO mirrors synced (N created); M DMP conflict(s) detected — run /calendar-cleanup to review.

End. Do not prompt.

Interactive mode

For each conflict, present:

• DMP event: title, time window, organizer (if available), recurrence status
• Wolf event causing the conflict: title, time window, calendar source

Then use AskUserQuestion with these options:

• Keep — do nothing.
• Set free — update the DMP event with availability: "free", span: "this-event". Best when you'll attend remotely or briefly without blocking the slot.
• Delete this instance — delete the DMP event with span: "this-event". Warning to display: "This removes the event from your local calendar but does NOT notify the organizer. Use 'Open in Calendar.app' if you need a real decline."
• Open in Calendar.app — surface the event ID and instruct the user to decline manually in Calendar.app or Outlook (only this path triggers the actual decline-with-response).
• Skip — leave for a future run.

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Tag taxonomy

Curated starting list (open vocabulary — extensible during a run):

• #appointment/medical — doctor, dentist, PT, therapy, vision, etc.
• #firearms — generic firearms-related
• #firearms/training — dry-fire, live-fire training, classes
• #firearms/competition — matches, leagues (use alongside more specific tags)
• #USPSA — USPSA-specific (matches, RO duty, classifiers)

Inference: consider both the event title and any existing note content. Multiple tags on one event are fine and often correct (e.g., a USPSA classifier match earns both #firearms/competition and #USPSA). When the title strongly suggests a category not in this list, propose the new tag explicitly so the user can confirm and extend the taxonomy.

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Capability notes

The Apple Events MCP cannot send a true decline response to a meeting organizer — there's no participant-status / response-action field exposed. The skill's Delete this instance option removes the event from the local calendar but does NOT notify the organizer. When a real decline-with-response is needed (organizer should know you can't attend), the user must do it in Calendar.app or Outlook directly. The Open in Calendar.app option in the conflict prompt is the path for that case.

Limitations not addressed in v1 (flagged as future improvements):

• Orphan mirrors: Wolf OoO events whose source event has been deleted or moved are not cleaned up.
• Recurrence on mirrors: mirrors are per-instance, not pattern-based. Each daily run picks up newly-in-window instances.
• True decline-with-response: requires Microsoft Graph API or Outlook scripting, not Apple Events MCP.

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Final summary

Emit a single final line summarizing the run:

• Auto: Calendar cleanup: OoO mirrors synced (N created); M DMP conflict(s) detected — run /calendar-cleanup to review. (or the no-conflict variant)
• Interactive: Calendar cleanup complete: N OoO mirrors created, T tag lines added, R conflicts resolved (S skipped).