From 459f7f3b645b82a287a91bc4dfc8ef30a8ce517a Mon Sep 17 00:00:00 2001
From: j2h4u <39818683+j2h4u@users.noreply.github.com>
Date: Wed, 4 Mar 2026 03:12:53 +0500
Subject: [PATCH] fix(roadmap): mark individual plan checkboxes when summaries
 exist

`cmdRoadmapUpdatePlanProgress` only marked phase-level checkboxes
(e.g. `- [ ] Phase 50: Build`) but skipped plan-level entries
(e.g. `- [ ] 50-01-PLAN.md`). Now iterates phase summaries and
marks matching plan checkboxes as complete.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 get-shit-done/bin/lib/roadmap.cjs | 12 +++++++++++
 tests/roadmap.test.cjs            | 36 +++++++++++++++++++++++++++++++
 2 files changed, 48 insertions(+)

diff --git a/get-shit-done/bin/lib/roadmap.cjs b/get-shit-done/bin/lib/roadmap.cjs
index a2fe661a6..6dd3554c6 100644
--- a/get-shit-done/bin/lib/roadmap.cjs
+++ b/get-shit-done/bin/lib/roadmap.cjs
@@ -287,6 +287,18 @@ function cmdRoadmapUpdatePlanProgress(cwd, phaseNum, raw) {
     roadmapContent = replaceInCurrentMilestone(roadmapContent, checkboxPattern, `$1x$2 (completed ${today})`);
   }
 
+  // Mark completed plan checkboxes (e.g. "- [ ] 50-01-PLAN.md" or "- [ ] 50-01:")
+  for (const summaryFile of phaseInfo.summaries) {
+    const planId = summaryFile.replace('-SUMMARY.md', '').replace('SUMMARY.md', '');
+    if (!planId) continue;
+    const planEscaped = escapeRegex(planId);
+    const planCheckboxPattern = new RegExp(
+      `(-\\s*\\[) (\\]\\s*${planEscaped})`,
+      'i'
+    );
+    roadmapContent = roadmapContent.replace(planCheckboxPattern, '$1x$2');
+  }
+
   fs.writeFileSync(roadmapPath, roadmapContent, 'utf-8');
 
   output({
diff --git a/tests/roadmap.test.cjs b/tests/roadmap.test.cjs
index ea5e2f538..7f41055a3 100644
--- a/tests/roadmap.test.cjs
+++ b/tests/roadmap.test.cjs
@@ -756,6 +756,42 @@ describe('roadmap update-plan-progress command', () => {
     assert.strictEqual(output.updated, false, 'should not update');
     assert.ok(output.reason.includes('ROADMAP.md not found'), 'reason should mention missing ROADMAP.md');
   });
+
+  test('marks completed plan checkboxes', () => {
+    const roadmapContent = `# Roadmap
+
+- [ ] Phase 50: Build
+  - [ ] 50-01-PLAN.md
+  - [ ] 50-02-PLAN.md
+
+### Phase 50: Build
+**Goal:** Build stuff
+**Plans:** 2 plans
+
+## Progress
+
+| Phase | Plans Complete | Status | Completed |
+|-------|---------------|--------|-----------|
+| 50. Build | 0/2 | Planned |  |
+`;
+    fs.writeFileSync(path.join(tmpDir, '.planning', 'ROADMAP.md'), roadmapContent);
+
+    const p50 = path.join(tmpDir, '.planning', 'phases', '50-build');
+    fs.mkdirSync(p50, { recursive: true });
+    fs.writeFileSync(path.join(p50, '50-01-PLAN.md'), '# Plan 1');
+    fs.writeFileSync(path.join(p50, '50-02-PLAN.md'), '# Plan 2');
+    // Only plan 1 has a summary (completed)
+    fs.writeFileSync(path.join(p50, '50-01-SUMMARY.md'), '# Summary 1');
+
+    const result = runGsdTools('roadmap update-plan-progress 50', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+
+    const roadmap = fs.readFileSync(path.join(tmpDir, '.planning', 'ROADMAP.md'), 'utf-8');
+    assert.ok(roadmap.includes('[x] 50-01-PLAN.md') || roadmap.includes('[x] 50-01'),
+      'completed plan checkbox should be marked');
+    assert.ok(roadmap.includes('[ ] 50-02-PLAN.md') || roadmap.includes('[ ] 50-02'),
+      'incomplete plan checkbox should remain unchecked');
+  });
 });
 
 // ─────────────────────────────────────────────────────────────────────────────