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>

Author: j2h4u

CHANGELOG.md

@@ -6,6 +6,9 @@ Format follows [Keep a Changelog](https://keepachangelog.com/en/1.1.0/).
 
 ## [Unreleased]
 
+### Fixed
+- `roadmap update-plan-progress` now marks individual plan checkboxes (e.g. `- [ ] 50-01-PLAN.md`) as complete when their summary exists
+
 ## [1.22.4] - 2026-03-03
 
 ### Added

get-shit-done/bin/lib/roadmap.cjs

@@ -279,6 +279,18 @@ function cmdRoadmapUpdatePlanProgress(cwd, phaseNum, raw) {
     roadmapContent = roadmapContent.replace(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({

tests/roadmap.test.cjs

@@ -662,6 +662,42 @@ 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');
+  });
 });
 
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