msd-core/get-shit-done/workflows/new-milestone.md

Start a new milestone cycle for an existing project. Loads project context, gathers milestone goals (from MILESTONE-CONTEXT.md or conversation), updates PROJECT.md and STATE.md, optionally runs parallel research, defines scoped requirements with REQ-IDs, spawns the roadmapper to create phased execution plan, and commits all artifacts. Brownfield equivalent of new-project.

<required_reading>

Read all files referenced by the invoking prompt's execution_context before starting.

</required_reading>

<available_agent_types> Valid GSD subagent types (use exact names — do not fall back to 'general-purpose'):

• gsd-project-researcher — Researches project-level technical decisions
• gsd-research-synthesizer — Synthesizes findings from parallel research agents
• gsd-roadmapper — Creates phased execution roadmaps </available_agent_types>

1. Load Context

Parse $ARGUMENTS before doing anything else:

• --reset-phase-numbers flag → opt into restarting roadmap phase numbering at 1
• remaining text → use as milestone name if present

If the flag is absent, keep the current behavior of continuing phase numbering from the previous milestone.

• Read PROJECT.md (existing project, validated requirements, decisions)
• Read MILESTONES.md (what shipped previously)
• Read STATE.md (pending todos, blockers)
• Check for MILESTONE-CONTEXT.md (from /gsd-discuss-milestone)

2. Gather Milestone Goals

If MILESTONE-CONTEXT.md exists:

• Use features and scope from discuss-milestone
• Present summary for confirmation

If no context file:

• Present what shipped in last milestone

Text mode (workflow.text_mode: true in config or --text flag): Set TEXT_MODE=true if --text is present in $ARGUMENTS OR text_mode from init JSON is true. When TEXT_MODE is active, replace every AskUserQuestion call with a plain-text numbered list and ask the user to type their choice number. This is required for non-Claude runtimes (OpenAI Codex, Gemini CLI, etc.) where AskUserQuestion is not available.

• Ask inline (freeform, NOT AskUserQuestion): "What do you want to build next?"
• Wait for their response, then use AskUserQuestion to probe specifics
• If user selects "Other" at any point to provide freeform input, ask follow-up as plain text — not another AskUserQuestion

2.5. Scan Planted Seeds

Check .planning/seeds/ for seed files that match the milestone goals gathered in step 2.

ls .planning/seeds/SEED-*.md 2>/dev/null

If no seed files exist: Skip this step silently — do not print any message or prompt.

If seed files exist: Read each SEED-*.md file and extract from its frontmatter and body:

• Idea — the seed title (heading after frontmatter, e.g. # SEED-001: <idea>)
• Trigger conditions — the trigger_when frontmatter field and the "When to Surface" section's bullet list
• Planted during — the planted_during frontmatter field (for context)

Compare each seed's trigger conditions against the milestone goals from step 2. A seed matches when its trigger conditions are relevant to any of the milestone's target features or goals.

If no seeds match: Skip silently — do not prompt the user.

If matching seeds found:

--auto mode: Auto-select ALL matching seeds. Log: [auto] Selected N matching seed(s): [list seed names]

Text mode (TEXT_MODE=true): Present matching seeds as a plain-text numbered list:

Seeds that match your milestone goals:
1. SEED-001: <idea> (trigger: <trigger_when>)
2. SEED-003: <idea> (trigger: <trigger_when>)

Enter numbers to include (comma-separated), or "none" to skip:

Normal mode: Present via AskUserQuestion:

AskUserQuestion(
  header: "Seeds",
  question: "These planted seeds match your milestone goals. Include any in this milestone's scope?",
  multiSelect: true,
  options: [
    { label: "SEED-001: <idea>", description: "Trigger: <trigger_when> | Planted during: <planted_during>" },
    ...
  ]
)

After selection:

• Selected seeds become additional context for requirement definition in step 9. Store them in an accumulator (e.g. $SELECTED_SEEDS) so step 9 can reference the ideas and their "Why This Matters" sections when defining requirements.
• Unselected seeds remain untouched in .planning/seeds/ — never delete or modify seed files during this workflow.

3. Determine Milestone Version

• Parse last version from MILESTONES.md
• Suggest next version (v1.0 → v1.1, or v2.0 for major)
• Confirm with user

3.5. Verify Milestone Understanding

Before writing any files, present a summary of what was gathered and ask for confirmation.

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► MILESTONE SUMMARY
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**Milestone v[X.Y]: [Name]**

**Goal:** [One sentence]

**Target features:**
- [Feature 1]
- [Feature 2]
- [Feature 3]

**Key context:** [Any important constraints, decisions, or notes from questioning]

AskUserQuestion:

• header: "Confirm?"
• question: "Does this capture what you want to build in this milestone?"
• options:
  • "Looks good" — Proceed to write PROJECT.md
  • "Adjust" — Let me correct or add details

If "Adjust": Ask what needs changing (plain text, NOT AskUserQuestion). Incorporate changes, re-present the summary. Loop until "Looks good" is selected.

If "Looks good": Proceed to Step 4.

4. Update PROJECT.md

Add/update:

## Current Milestone: v[X.Y] [Name]

**Goal:** [One sentence describing milestone focus]

**Target features:**
- [Feature 1]
- [Feature 2]
- [Feature 3]

Update Active requirements section and "Last updated" footer.

Ensure the ## Evolution section exists in PROJECT.md. If missing (projects created before this feature), add it before the footer:

## Evolution

This document evolves at phase transitions and milestone boundaries.

**After each phase transition** (via `/gsd-transition`):
1. Requirements invalidated? → Move to Out of Scope with reason
2. Requirements validated? → Move to Validated with phase reference
3. New requirements emerged? → Add to Active
4. Decisions to log? → Add to Key Decisions
5. "What This Is" still accurate? → Update if drifted

**After each milestone** (via `/gsd-complete-milestone`):
1. Full review of all sections
2. Core Value check — still the right priority?
3. Audit Out of Scope — reasons still valid?
4. Update Context with current state

5. Update STATE.md

## Current Position

Phase: Not started (defining requirements)
Plan: —
Status: Defining requirements
Last activity: [today] — Milestone v[X.Y] started

Keep Accumulated Context section from previous milestone.

6. Cleanup and Commit

Delete MILESTONE-CONTEXT.md if exists (consumed).

Clear leftover phase directories from the previous milestone:

gsd-sdk query phases.clear --confirm

gsd-sdk query commit "docs: start milestone v[X.Y] [Name]" .planning/PROJECT.md .planning/STATE.md

7. Load Context and Resolve Models

INIT=$(gsd-sdk query init.new-milestone)
if [[ "$INIT" == @file:* ]]; then INIT=$(cat "${INIT#@file:}"); fi
AGENT_SKILLS_RESEARCHER=$(gsd-sdk query agent-skills gsd-project-researcher 2>/dev/null)
AGENT_SKILLS_SYNTHESIZER=$(gsd-sdk query agent-skills gsd-synthesizer 2>/dev/null)
AGENT_SKILLS_ROADMAPPER=$(gsd-sdk query agent-skills gsd-roadmapper 2>/dev/null)

Extract from init JSON: researcher_model, synthesizer_model, roadmapper_model, commit_docs, research_enabled, current_milestone, project_exists, roadmap_exists, latest_completed_milestone, phase_dir_count, phase_archive_path.

7.5 Reset-phase safety (only when --reset-phase-numbers)

If --reset-phase-numbers is active:

1. Set starting phase number to 1 for the upcoming roadmap.
2. If phase_dir_count > 0, archive the old phase directories before roadmapping so new 01-* / 02-* directories cannot collide with stale milestone directories.

If phase_dir_count > 0 and phase_archive_path is available:

mkdir -p "${phase_archive_path}"
find .planning/phases -mindepth 1 -maxdepth 1 -type d -exec mv {} "${phase_archive_path}/" \;

Then verify .planning/phases/ no longer contains old milestone directories before continuing.

If phase_dir_count > 0 but phase_archive_path is missing:

• Stop and explain that reset numbering is unsafe without a completed milestone archive target.
• Tell the user to complete/archive the previous milestone first, then rerun /gsd-new-milestone --reset-phase-numbers ${GSD_WS}.

8. Research Decision

Check research_enabled from init JSON (loaded from config).

If research_enabled is true:

AskUserQuestion: "Research the domain ecosystem for new features before defining requirements?"

• "Research first (Recommended)" — Discover patterns, features, architecture for NEW capabilities
• "Skip research for this milestone" — Go straight to requirements (does not change your default)

If research_enabled is false:

AskUserQuestion: "Research the domain ecosystem for new features before defining requirements?"

• "Skip research (current default)" — Go straight to requirements
• "Research first" — Discover patterns, features, architecture for NEW capabilities

IMPORTANT: Do NOT persist this choice to config.json. The workflow.research setting is a persistent user preference that controls plan-phase behavior across the project. Changing it here would silently alter future /gsd-plan-phase behavior. To change the default, use /gsd-settings.

If user chose "Research first":

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
 GSD ► RESEARCHING
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

◆ Spawning 4 researchers in parallel...
  → Stack, Features, Architecture, Pitfalls

mkdir -p .planning/research

Spawn 4 parallel gsd-project-researcher agents. Each uses this template with dimension-specific fields:

Common structure for all 4 researchers:

Task(prompt="
<research_type>Project Research — {DIMENSION} for [new features].</research_type>

<milestone_context>
SUBSEQUENT MILESTONE — Adding [target features] to existing app.
{EXISTING_CONTEXT}
Focus ONLY on what's needed for the NEW features.
</milestone_context>

<question>{QUESTION}</question>

<files_to_read>
- .planning/PROJECT.md (Project context)
</files_to_read>

${AGENT_SKILLS_RESEARCHER}

<downstream_consumer>{CONSUMER}</downstream_consumer>

<quality_gate>{GATES}</quality_gate>

<output>
Write to: .planning/research/{FILE}
Use template: ~/.claude/get-shit-done/templates/research-project/{FILE}
</output>
", subagent_type="gsd-project-researcher", model="{researcher_model}", description="{DIMENSION} research")

Dimension-specific fields:

Field	Stack	Features	Architecture	Pitfalls
EXISTING_CONTEXT	Existing validated capabilities (DO NOT re-research): [from PROJECT.md]	Existing features (already built): [from PROJECT.md]	Existing architecture: [from PROJECT.md or codebase map]	Focus on common mistakes when ADDING these features to existing system
QUESTION	What stack additions/changes are needed for [new features]?	How do [target features] typically work? Expected behavior?	How do [target features] integrate with existing architecture?	Common mistakes when adding [target features] to [domain]?
CONSUMER	Specific libraries with versions for NEW capabilities, integration points, what NOT to add	Table stakes vs differentiators vs anti-features, complexity noted, dependencies on existing	Integration points, new components, data flow changes, suggested build order	Warning signs, prevention strategy, which phase should address it
GATES	Versions current (verify with Context7), rationale explains WHY, integration considered	Categories clear, complexity noted, dependencies identified	Integration points identified, new vs modified explicit, build order considers deps	Pitfalls specific to adding these features, integration pitfalls covered, prevention actionable
FILE	STACK.md	FEATURES.md	ARCHITECTURE.md	PITFALLS.md

After all 4 complete, spawn synthesizer:

Task(prompt="
Synthesize research outputs into SUMMARY.md.

<files_to_read>
- .planning/research/STACK.md
- .planning/research/FEATURES.md
- .planning/research/ARCHITECTURE.md
- .planning/research/PITFALLS.md
</files_to_read>

${AGENT_SKILLS_SYNTHESIZER}

Write to: .planning/research/SUMMARY.md
Use template: ~/.claude/get-shit-done/templates/research-project/SUMMARY.md
Commit after writing.
", subagent_type="gsd-research-synthesizer", model="{synthesizer_model}", description="Synthesize research")

Display key findings from SUMMARY.md:

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 GSD ► RESEARCH COMPLETE ✓
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**Stack additions:** [from SUMMARY.md]
**Feature table stakes:** [from SUMMARY.md]
**Watch Out For:** [from SUMMARY.md]

If "Skip research": Continue to Step 9.

9. Define Requirements

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 GSD ► DEFINING REQUIREMENTS
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Read PROJECT.md: core value, current milestone goals, validated requirements (what exists).

If $SELECTED_SEEDS is non-empty (from step 2.5): Include selected seed ideas and their "Why This Matters" sections as additional input when defining requirements. Seeds provide user-validated feature ideas that should be incorporated into the requirement categories alongside research findings or conversation-gathered features.

If research exists: Read FEATURES.md, extract feature categories.

Present features by category:

## [Category 1]
**Table stakes:** Feature A, Feature B
**Differentiators:** Feature C, Feature D
**Research notes:** [any relevant notes]

If no research: Gather requirements through conversation. Ask: "What are the main things users need to do with [new features]?" Clarify, probe for related capabilities, group into categories.

Scope each category via AskUserQuestion (multiSelect: true, header max 12 chars):

• "[Feature 1]" — [brief description]
• "[Feature 2]" — [brief description]
• "None for this milestone" — Defer entire category

Track: Selected → this milestone. Unselected table stakes → future. Unselected differentiators → out of scope.

Identify gaps via AskUserQuestion:

• "No, research covered it" — Proceed
• "Yes, let me add some" — Capture additions

Generate REQUIREMENTS.md:

• v1 Requirements grouped by category (checkboxes, REQ-IDs)
• Future Requirements (deferred)
• Out of Scope (explicit exclusions with reasoning)
• Traceability section (empty, filled by roadmap)

REQ-ID format: [CATEGORY]-[NUMBER] (AUTH-01, NOTIF-02). Continue numbering from existing.

Requirement quality criteria:

Good requirements are:

• Specific and testable: "User can reset password via email link" (not "Handle password reset")
• User-centric: "User can X" (not "System does Y")
• Atomic: One capability per requirement (not "User can login and manage profile")
• Independent: Minimal dependencies on other requirements

Present FULL requirements list for confirmation:

## Milestone v[X.Y] Requirements

### [Category 1]
- [ ] **CAT1-01**: User can do X
- [ ] **CAT1-02**: User can do Y

### [Category 2]
- [ ] **CAT2-01**: User can do Z

Does this capture what you're building? (yes / adjust)

If "adjust": Return to scoping.

Commit requirements:

gsd-sdk query commit "docs: define milestone v[X.Y] requirements" .planning/REQUIREMENTS.md

10. Create Roadmap

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 GSD ► CREATING ROADMAP
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◆ Spawning roadmapper...

Starting phase number:

• If --reset-phase-numbers is active, start at Phase 1
• Otherwise, continue from the previous milestone's last phase number (v1.0 ended at phase 5 → v1.1 starts at phase 6)

Task(prompt="
<planning_context>
<files_to_read>
- .planning/PROJECT.md
- .planning/REQUIREMENTS.md
- .planning/research/SUMMARY.md (if exists)
- .planning/config.json
- .planning/MILESTONES.md
</files_to_read>

${AGENT_SKILLS_ROADMAPPER}

</planning_context>

<instructions>
Create roadmap for milestone v[X.Y]:
1. Respect the selected numbering mode:
   - `--reset-phase-numbers` → start at Phase 1
   - default behavior → continue from the previous milestone's last phase number
2. Derive phases from THIS MILESTONE's requirements only
3. Map every requirement to exactly one phase
4. Derive 2-5 success criteria per phase (observable user behaviors)
5. Validate 100% coverage
6. Write files immediately (ROADMAP.md, STATE.md, update REQUIREMENTS.md traceability)
7. Return ROADMAP CREATED with summary

Write files first, then return.
</instructions>
", subagent_type="gsd-roadmapper", model="{roadmapper_model}", description="Create roadmap")

Handle return:

If ## ROADMAP BLOCKED: Present blocker, work with user, re-spawn.

If ## ROADMAP CREATED: Read ROADMAP.md, present inline:

## Proposed Roadmap

**[N] phases** | **[X] requirements mapped** | All covered ✓

| # | Phase | Goal | Requirements | Success Criteria |
|---|-------|------|--------------|------------------|
| [N] | [Name] | [Goal] | [REQ-IDs] | [count] |

### Phase Details

**Phase [N]: [Name]**
Goal: [goal]
Requirements: [REQ-IDs]
Success criteria:
1. [criterion]
2. [criterion]

Ask for approval via AskUserQuestion:

• "Approve" — Commit and continue
• "Adjust phases" — Tell me what to change
• "Review full file" — Show raw ROADMAP.md

If "Adjust": Get notes, re-spawn roadmapper with revision context, loop until approved. If "Review": Display raw ROADMAP.md, re-ask.

Commit roadmap (after approval):

gsd-sdk query commit "docs: create milestone v[X.Y] roadmap ([N] phases)" .planning/ROADMAP.md .planning/STATE.md .planning/REQUIREMENTS.md

11. Done

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 GSD ► MILESTONE INITIALIZED ✓
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

**Milestone v[X.Y]: [Name]**

| Artifact       | Location                    |
|----------------|-----------------------------|
| Project        | `.planning/PROJECT.md`      |
| Research       | `.planning/research/`       |
| Requirements   | `.planning/REQUIREMENTS.md` |
| Roadmap        | `.planning/ROADMAP.md`      |

**[N] phases** | **[X] requirements** | Ready to build ✓

## ▶ Next Up — [${PROJECT_CODE}] ${PROJECT_TITLE}

**Phase [N]: [Phase Name]** — [Goal]

`/clear` then:

`/gsd-discuss-phase [N] ${GSD_WS}` — gather context and clarify approach

Also: `/gsd-plan-phase [N] ${GSD_WS}` — skip discussion, plan directly

<success_criteria>

• PROJECT.md updated with Current Milestone section
• STATE.md reset for new milestone
• MILESTONE-CONTEXT.md consumed and deleted (if existed)
• Research completed (if selected) — 4 parallel agents, milestone-aware
• Requirements gathered and scoped per category
• REQUIREMENTS.md created with REQ-IDs
• gsd-roadmapper spawned with phase numbering context
• Roadmap files written immediately (not draft)
• User feedback incorporated (if any)
• Phase numbering mode respected (continued or reset)
• All commits made (if planning docs committed)
• User knows next step: /gsd-discuss-phase [N] ${GSD_WS}

Atomic commits: Each phase commits its artifacts immediately. </success_criteria>