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fix(skills): update plan file checkboxes after completing tasks#808

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hoklims wants to merge 2 commits intoobra:mainfrom
hoklims:fix/update-plan-checkboxes
Open

fix(skills): update plan file checkboxes after completing tasks#808
hoklims wants to merge 2 commits intoobra:mainfrom
hoklims:fix/update-plan-checkboxes

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@hoklims hoklims commented Mar 18, 2026

Summary

Fixes #789executing-plans and subagent-driven-development never updated plan file checkboxes (- [ ]- [x]), leaving all checkboxes unchecked even after full implementation.

Root cause: Both skills used only TodoWrite (ephemeral, session-scoped) for progress tracking. The plan file on disk was never modified, despite writing-plans promising checkbox tracking in the plan header.

Fix: Add explicit instructions for the orchestrator (not the subagent) to update checkboxes in the plan file using the Edit tool after each task completes.

Changes

  • skills/executing-plans/SKILL.md — Add step 5: update plan file checkboxes after task completion
  • skills/subagent-driven-development/SKILL.md — Add "Plan File Tracking" section, update process diagram node, update example workflow with checkbox update steps

Design decision

The orchestrator updates checkboxes (not the implementer subagent), because:

  • The task is only "done" after the two-stage review passes
  • Subagents shouldn't read/write the plan file (explicit SDD principle)
  • The orchestrator knows the plan file path and task boundaries

Testing

Verified with a fresh Claude Code instance (claude -p --plugin-dir <modified-plugin>):

Metric Before After
- [ ] (unchecked) 7 1 (header template only)
- [x] (checked) 0 6

All 6 task step checkboxes were updated after execution. The remaining - [ ] is in the plan header (syntax example, not a step).

Also verified:

  • No other mechanism in the codebase handles checkbox updates (grepped hooks, all skills)
  • No conflicts with existing functionality
  • Consistent with writing-plans promise: "Steps use checkbox syntax for tracking"

Both executing-plans and subagent-driven-development used only
TodoWrite (ephemeral) for progress tracking, leaving all plan file
checkboxes as `- [ ]` even after full implementation.

Add explicit instructions to update `- [ ]` to `- [x]` in the plan
file using the Edit tool after each task completes. This makes the
plan file a persistent progress record across sessions.

Changes:
- executing-plans: add step 5 to update checkboxes after task completion
- subagent-driven-development: add Plan File Tracking section, update
  process diagram node, and update example workflow

Fixes obra#789
Copilot AI review requested due to automatic review settings March 18, 2026 12:03
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Pull request overview

Updates the workflow documentation for plan execution to ensure progress is persisted back into the on-disk plan file (checkboxes), not only tracked in TodoWrite.

Changes:

  • Extend the subagent-driven-development process to include updating plan-file checkboxes after completing each task.
  • Add a “Plan File Tracking” section and update the example workflow to include the plan-file checkbox update step.
  • Update executing-plans to explicitly instruct updating the plan file checkboxes via the Edit tool.

Reviewed changes

Copilot reviewed 2 out of 2 changed files in this pull request and generated 2 comments.

File Description
skills/subagent-driven-development/SKILL.md Updates the per-task flow diagram and adds explicit guidance + examples for marking plan-file checkboxes complete.
skills/executing-plans/SKILL.md Adds an explicit step to update plan-file checkboxes after marking a task complete.

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## Plan File Tracking

After marking a task complete in TodoWrite, update the plan file on disk — change `- [ ]` to `- [x]` for all completed steps in that task using the Edit tool. This keeps the plan file as a persistent progress record across sessions.
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Fixed in 46c3286 — now uses `Edit` tool with backtick formatting.

2. Follow each step exactly (plan has bite-sized steps)
3. Run verifications as specified
4. Mark as completed
5. Update the plan file: change `- [ ]` to `- [x]` for completed steps using Edit tool
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Fixed in 46c3286 — now uses `Edit` tool with backtick formatting.

Address Copilot review feedback — consistent tool name formatting.
@obra obra added bug Something isn't working claude-code Claude Code (Anthropic CLI) issues plans Planning workflow (writing-plans, executing-plans) subagents Subagent-driven development and dispatch labels Mar 23, 2026
@infegz
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infegz commented Mar 30, 2026

When will this PR be merged and released? I was just about to open a related PR and I found it. 😂

@PGoski
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PGoski commented Apr 5, 2026

+1

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bug Something isn't working claude-code Claude Code (Anthropic CLI) issues plans Planning workflow (writing-plans, executing-plans) subagents Subagent-driven development and dispatch

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executing-plans and subagent-driven-development don't update plan file checkboxes

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