ADD Milestone Command v0.9.10

ADD Milestone Command v0.9.10

Manage milestones directly — list status, switch active milestone, split large milestones, rescope features, or create new ones. This is the tactical companion to /add:roadmap (strategic horizon planning).

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Pre-Flight

All subcommands start here:

1. Read .add/config.json — extract maturity.level, planning.current_milestone, planning.current_cycle
   • If not found: abort with "No ADD project found. Run /add:init first."
2. Glob docs/milestones/M*.md — discover all milestone files
3. Parse each milestone file — extract:
   • Status (NOT_STARTED / IN_PROGRESS / COMPLETE)
   • Goal (first line under ## Goal)
   • Features (from Feature Detail table: name, position, spec link)
   • Success criteria (count checked [x] vs total [ ])
4. Read docs/prd.md Section 6 — cross-reference horizon placement (Now/Next/Later) from the roadmap table
5. Read .add/handoff.md if it exists — note any in-progress decisions relevant to milestone changes
6. Determine subcommand from arguments. Default: --list

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Command: /milestone --list (default)

Display all milestones with live status. No file modifications.

Output

Milestones Overview
Active: {planning.current_milestone or "None"}

| # | Milestone | Status | Horizon | Features | Complete | Target |
|---|-----------|--------|---------|----------|----------|--------|
| → | M1-foundation | IN_PROGRESS | NOW | 5 | 40% (2/5) | alpha |
|   | M2-scaling | NOT_STARTED | NEXT | 3 | 0% (0/3) | beta |
|   | M3-enterprise | NOT_STARTED | LATER | 4 | 0% (0/4) | ga |

• → marks the active milestone
• Completion % = features at VERIFIED or DONE / total features
• Horizon comes from PRD roadmap table; show "?" if milestone not in PRD

Maturity Scaling

• POC/Alpha: Table as shown above
• Beta/GA: Add columns for Appetite Remaining, Risk Count, Cycle Count

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Command: /milestone --switch

Switch the active milestone. Accepts milestone ID like M2-scaling or just M2.

Step 1: Resolve Target

Find the milestone file matching the argument:

• Try docs/milestones/{id}.md directly
• Try docs/milestones/M{N}-*.md glob if only a number given
• If no match: "Milestone '{id}' not found. Run /add:milestone --list to see available milestones."

Step 2: Safety Checks

If target is COMPLETE:

M1-foundation is marked COMPLETE.
Switching to a completed milestone is unusual — are you sure?
(This won't reopen it, but new cycles would target it.)

Ask via AskUserQuestion. Proceed only if confirmed.

If current milestone has IN_PROGRESS features:

Current milestone {name} has features in progress:
  - Auth Overhaul (IN_PROGRESS, cycle-8)
  - Session Refresh (PLANNED, cycle-8)

These will remain in their current state. Continue?

Ask via AskUserQuestion.

If active cycle exists (check .add/cycles/ for non-COMPLETE cycles):

Active cycle {cycle-N} is tied to {current_milestone}.
Switching milestones won't close this cycle. You may want to
run /add:cycle --complete first, or the cycle will be orphaned.

Continue anyway?

Step 3: Apply Switch

1. Update .add/config.json:
   • Set planning.current_milestone to target milestone ID
   • Scan .add/cycles/ for cycles referencing the target milestone; set planning.current_cycle to the latest non-COMPLETE one, or null if none
2. If target milestone Status is NOT_STARTED:
   • Update milestone file: set Status: IN_PROGRESS, set Started: {TODAY}
3. Present summary:

Switched active milestone:
  From: M1-foundation (IN_PROGRESS)
  To:   M2-scaling (now IN_PROGRESS)

Config updated:
  planning.current_milestone → "M2-scaling"
  planning.current_cycle → null (no existing cycles for M2)

Next: Run /add:cycle --plan to plan the first cycle for M2.

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Command: /milestone --split

Split a milestone into two. Interactive interview to redistribute features.

Step 1: Load and Display

Read the target milestone file. Display:

Splitting: M3 — Marketplace Ready
Goal: Build and launch the marketplace feature set
Features (6):
  1. Product Listings (SPECCED)
  2. Search & Filter (SHAPED)
  3. Shopping Cart (SHAPED)
  4. Checkout Flow (SHAPED)
  5. Seller Dashboard (SHAPED)
  6. Order Management (SHAPED)

Step 2: Interview (5 questions, 1-by-1)

Q1: "What's the split point? List the feature numbers that stay in the original milestone." → Captures: feature distribution

Q2: "What's the goal for the NEW milestone? (The original milestone keeps its current goal unless you change it.)" → Captures: new milestone goal

Q3: "Name for the new milestone? (Suggestion: M{next}-{slug})" → Captures: new milestone ID and name

Q4: "Appetite for each? Redistribute the original budget or set new ones." → Captures: appetite for both milestones

Q5: "Where does the new milestone sit in the roadmap? (Now/Next/Later)" → Captures: horizon placement

Step 3: Confirm

Split plan:

ORIGINAL: M3 — Marketplace Ready (keeps 3 features)
  Features: Product Listings, Search & Filter, Shopping Cart
  Appetite: 2 weeks
  Horizon: NOW

NEW: M4 — Seller Experience (gets 3 features)
  Features: Checkout Flow, Seller Dashboard, Order Management
  Appetite: 3 weeks
  Horizon: NEXT

Files to create/modify:
  - docs/milestones/M3-marketplace-ready.md (remove 3 features)
  - docs/milestones/M4-seller-experience.md (NEW)
  - docs/prd.md (add M4 to roadmap table)
  - .add/config.json (no change — M3 stays active)

Proceed?

Step 4: Apply

1. Edit original milestone file — remove redistributed features from Hill Chart and Feature Detail table
2. Create new milestone file from ${CLAUDE_PLUGIN_ROOT}/templates/milestone.md.template — populate with moved features (keep their current positions), goal, appetite
3. Update docs/prd.md Section 6 — add new milestone row to roadmap table at the specified horizon
4. If original milestone was the active one and all its remaining features are DONE, flag it

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Command: /milestone --rescope

Interactively move features between milestones. Lighter than split — for fine-tuning scope.

Step 1: Display Current State

Show features in the target milestone and adjacent milestones:

Rescoping: M2 — Scaling (3 features)

M2 features:
  1. Load Balancer Setup (IN_PROGRESS)
  2. Database Sharding (SPECCED)
  3. CDN Integration (SHAPED)

Adjacent milestones:
  M1 — Foundation (5 features): Auth, Users, Profiles, Settings, Onboarding
  M3 — Enterprise (4 features): SSO, Audit Log, RBAC, Compliance

Step 2: Interactive Rescoping

Ask 1-by-1:

Q1: "Move any features OUT of M2? (List numbers, or 'none')" → If yes: "Where should each go? (target milestone ID)"

Q2: "Move any features IN from other milestones? (List as 'M1:Auth, M3:SSO', or 'none')"

Q3: "Add any brand new features? (Name + brief description, or 'none')" → If yes, note: "New features will be added at SHAPED position. Create specs with /add:spec."

Q4: "Should M2's goal or appetite change given the new scope?"

Step 3: Confirm and Apply

Show change summary. On confirmation:

1. Edit source milestone — remove outgoing features
2. Edit target milestones — add incoming features at their current position
3. Edit rescoped milestone — add new features at SHAPED, update goal/appetite if changed
4. Update PRD Section 6 if milestone scope changed significantly
5. Append to PRD Section 10 (Revision History): | {DATE} | {VERSION} | milestone | Rescoped {milestone}: {summary of changes} |
6. Update .add/handoff.md if it exists — note the rescoping for session continuity

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Command: /milestone --create

Create a new milestone from scratch with a lightweight interview.

Interview (scaled by maturity)

All maturities:

Q1: "What's the milestone goal? (1-2 sentences — what does 'done' look like?)"

Q2: "Name? (Suggestion: M{next_number}-{slug})"

Q3: "Roadmap horizon? (Now / Next / Later)"

Alpha+:

Q4: "Effort appetite? (e.g., '2 weeks', '3 cycles', 'exploratory')"

Q5: "Known features to include? (Comma-separated names, or 'none yet')"

Beta+:

Q6: "Success criteria? (List 3-5 measurable signals of completion)"

Q7: "Any dependencies on other milestones or external factors?"

Q8: "Target maturity level for this milestone? (poc/alpha/beta/ga)"

Generate

1. Determine next milestone number from existing files
2. Create docs/milestones/M{N}-{slug}.md from ${CLAUDE_PLUGIN_ROOT}/templates/milestone.md.template
3. Populate: Goal, Status: NOT_STARTED, Features (all at SHAPED), Appetite, Success Criteria, Dependencies
4. Update docs/prd.md Section 6 — add row to roadmap table at the specified horizon
5. If no active milestone exists, offer: "No active milestone set. Switch to M{N}? (y/n)"
   • If yes, update planning.current_milestone in config

Present

Milestone created: docs/milestones/M{N}-{slug}.md

Goal: {goal}
Horizon: {horizon}
Features: {count} (all SHAPED)
Appetite: {appetite}

Next steps:
  1. Create specs for features: /add:spec {feature-name}
  2. Switch to this milestone: /add:milestone --switch M{N}
  3. Plan first cycle: /add:cycle --plan

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Error Handling

No milestones exist:

• --list: "No milestones found. Create one with /add:milestone --create or run /add:init."
• --switch/--split/--rescope: "Milestone not found."

Milestone file unparseable:

• Skip in --list, show warning
• For targeted commands, report: "Could not parse {file}. Check the file format against the milestone template."

PRD Section 6 missing:

• Commands still work (milestones are the source of truth for content)
• Warn: "PRD roadmap table not found — milestone files updated but PRD not synced. Run /add:roadmap --edit to rebuild."

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Integration

Skill	Relationship
/add:cycle	Reads planning.current_milestone. Milestone skill sets this value.
/add:roadmap	Manages horizon placement. Milestone skill manages content and switching.
/add:spec	Creates feature specs listed in milestones.
/add:promote	Milestone completion can trigger promotion readiness.