Update Milestones

Sync MILESTONES.md with work completed in workflow docs. Detects checkbox changes and updates milestone items.

Boundaries

This skill MAY: read .unipi/docs/, update .unipi/docs/MILESTONES.md, ask user for conflict resolution. This skill MAY NOT: modify workflow docs, delete files, create new milestones (use /unipi:milestone-onboard).

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Phase 1: Scan

Read all workflow docs modified since last milestone update.

1. Read .unipi/docs/MILESTONES.md — if missing, suggest /unipi:milestone-onboard
2. Record updated date from MILESTONES.md frontmatter
3. Scan .unipi/docs/{specs,plans,quick-work}/ for files modified after the updated date
4. If no modified files found:

   "No workflow docs have been modified since the last milestone update."

5. List modified files and present to user

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Phase 2: Diff

Compare checkbox states between current docs and baseline.

1. For each modified file:
   • Extract all checkbox items (- [ ] and - [x])
   • Extract task statuses from plans (completed:)
2. Compare against MILESTONES.md items:
   • Exact match (normalized): item text matches a milestone item
   • No match: item not found in milestones
3. Categorize:
   • Newly completed: item is [x] in doc but [ ] in milestones
   • Already synced: item matches milestone state
   • Unmatched: item not in milestones at all
4. Present diff:

   "Found 3 changes:

   • ✅ Authentication system — completed in spec.md (exact match)
   • ✅ API routing — completed in plan.md (exact match)
   • ⚠️ New feature idea — not found in milestones (skipped)"

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Phase 3: Resolve

Auto-update clear matches, ask user on conflicts.

1. Exact matches: Update automatically via updateItemStatus()
2. Unmatched completions: Present to user via ask_user:

   "Found completed items not in milestones:

   1. New feature idea (from spec.md)

   What should I do?"

   • Skip (don't update milestones)
   • Add to a phase (specify which)

3. If user wants to add: ask which phase, then add item and mark as completed
4. Log all changes made

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Phase 4: Write

Apply resolved changes to MILESTONES.md.

1. For each resolved change:
   • Call updateItemStatus(milestonesPath, phase, text, true) for completions
   • Or modify doc directly for new items
2. Update updated frontmatter date to today
3. Verify file still parses correctly

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Phase 5: Report

Show what changed, what was skipped, suggest next steps.

1. Display summary:

   "✅ Milestones updated:

   • 2 items marked complete
   • 1 item skipped (not in milestones)

   Progress: 5/10 items (50%) Current phase: Phase 1: Foundation (3/5 done)

   Next steps:

   • Continue with remaining items
   • /unipi:milestone-onboard — restructure milestones"

2. If no changes were made:

   "No milestone items needed updating. Everything is in sync."

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Validation Checklist

Before completing, verify:

• MILESTONES.md still exists and is valid
• All auto-updated items match their source docs
• updated date reflects today
• No items were accidentally unchecked
• File parses correctly via parseMilestones()