Context (pre-injected)

Roadmap:

State:

plan-milestone workflow

Plan all unplanned phases in the current milestone in a single orchestrated session.

Mode Selection (step 0 - always first)

Ask the user ONE binary question:

"Should I ask you questions during planning, or plan everything silently and flag doubts at the end?"

Interactive - I'll ask targeted questions per phase when I hit real ambiguity

Silent - Plan autonomously; collect flags for review at the end

Store the answer as MODE (interactive | silent). Do not ask again.

Phase Discovery

pi-gsd-tools roadmap analyze --raw
pi-gsd-tools state json --raw

Identify all phases with no PLAN.md files in their phase directory. Skip phases already Complete or already planned. Work in roadmap order.

Per-Phase Planning Loop

For each unplanned phase N:

1. Scope Pre-check

Read .planning/REQUIREMENTS.md and the phase entry from ROADMAP.md (goal + success criteria).

Ask internally: "Does executing this phase risk implementing anything not covered by active requirements, or conflict with what previous phases were meant to deliver?"

Classify risk:

low - continue silently
medium - log in scope-notes, continue
high + interactive - surface to user before proceeding, ask whether to adjust or continue
high + silent - log prominently, continue, surface in final summary

2. Plan the Phase

Invoke:

Skill(skill="gsd-plan-phase", args="${N} --skip-research")

Unless the phase has no RESEARCH.md yet → drop --skip-research. In silent mode, append --auto to suppress discussion prompts inside plan-phase.

3. Checkpoint

After each phase plan is committed:

pi-gsd-tools state update current_phase ${N}

Announce: ✓ Phase ${N} planned - ${plan_count} plan(s) created

Check context remaining. If < 25%: stop immediately, emit summary of planned vs remaining phases, suggest /gsd-plan-milestone --from ${next_unplanned} to continue.

Final Summary

━━ plan-milestone complete ━━━━━━━━━━━━━━━━━━━━━━━
✓ Planned:  [phase list]
⚠ Flags:   [scope notes from high-risk pre-checks]
↳ Next: /gsd-execute-milestone
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

If flags exist and MODE=interactive: present them for user review before suggesting execute-milestone. If flags exist and MODE=silent: present all flags together at the end.

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