diff --git a/.changeset/vivid-jaguars-tumble.md b/.changeset/vivid-jaguars-tumble.md
new file mode 100644
index 000000000..5c9a3d0f8
--- /dev/null
+++ b/.changeset/vivid-jaguars-tumble.md
@@ -0,0 +1,5 @@
+---
+type: Fixed
+pr: 3794
+---
+Annotate-dependencies now matches all Plans-block heading variants in PLAN.md so downstream wave assignment is correct.
diff --git a/get-shit-done/bin/lib/init.cjs b/get-shit-done/bin/lib/init.cjs
index 04fc77cbd..80029a21f 100644
--- a/get-shit-done/bin/lib/init.cjs
+++ b/get-shit-done/bin/lib/init.cjs
@@ -1170,7 +1170,9 @@ function cmdInitManager(cwd, raw) {
 
     const sectionStart = match.index;
     const restOfContent = content.slice(sectionStart);
-    const nextHeader = restOfContent.match(/\n#{2,4}\s+Phase\s+\d/i);
+    // #3691: `\d` → `\d[\d.]*` so decimal phase headings (e.g. `### Phase 02.3:`) are
+    // recognised as section boundaries.
+    const nextHeader = restOfContent.match(/\n#{2,4}\s+Phase\s+\d[\d.]*/i);
     const sectionEnd = nextHeader ? sectionStart + nextHeader.index : content.length;
     const section = content.slice(sectionStart, sectionEnd);
 
diff --git a/get-shit-done/bin/lib/phase.cjs b/get-shit-done/bin/lib/phase.cjs
index dbea48464..f197ac9ba 100644
--- a/get-shit-done/bin/lib/phase.cjs
+++ b/get-shit-done/bin/lib/phase.cjs
@@ -882,7 +882,9 @@ function cmdPhaseInsert(cwd, afterPhase, description, raw) {
 
       const headerIdx = rawContent.indexOf(headerMatch[0]);
       const afterHeader = rawContent.slice(headerIdx + headerMatch[0].length);
-      const nextPhaseMatch = afterHeader.match(/\n#{2,4}\s+Phase\s+\d/i);
+      // #3691: `\d` → `\d[\d.]*` so decimal phase headings (e.g. `### Phase 02.3:`) are
+      // recognised as section boundaries.
+      const nextPhaseMatch = afterHeader.match(/\n#{2,4}\s+Phase\s+\d[\d.]*/i);
 
       let insertIdx;
       if (nextPhaseMatch) {
diff --git a/get-shit-done/bin/lib/roadmap.cjs b/get-shit-done/bin/lib/roadmap.cjs
index 901b0d3a9..441bddb20 100644
--- a/get-shit-done/bin/lib/roadmap.cjs
+++ b/get-shit-done/bin/lib/roadmap.cjs
@@ -223,7 +223,9 @@ function cmdRoadmapAnalyze(cwd, raw) {
     // Extract goal from the section
     const sectionStart = match.index;
     const restOfContent = content.slice(sectionStart);
-    const nextHeader = restOfContent.match(/\n#{2,4}\s+Phase\s+\d/i);
+    // #3691: `\d` → `\d[\d.]*` so decimal phase headings (e.g. `### Phase 02.3:`) are
+    // recognised as section boundaries.
+    const nextHeader = restOfContent.match(/\n#{2,4}\s+Phase\s+\d[\d.]*/i);
     const sectionEnd = nextHeader ? sectionStart + nextHeader.index : content.length;
     const section = content.slice(sectionStart, sectionEnd);
 
@@ -549,8 +551,19 @@ function cmdRoadmapAnnotateDependencies(cwd, phaseNum, raw) {
       /\*\*Cross-cutting constraints:\*\*/i.test(phaseSection)
     ) return;
 
-    // Find the Plans: section within the phase section
-    const plansBlockMatch = phaseSection.match(/(Plans:\s*\n)((?:\s*-\s*\[[ x]\][^\n]*\n?)*)/i);
+    // Find the Plans: section within the phase section.
+    // #3691 Bug 1: `Plans:\s*\n` required no text after the colon, missing variants like
+    // `Plans: 3 plans across 2 waves\n` or `**Plans:** 3 plans\n` (bold-wrapped).
+    // `\*{0,2}Plans\*{0,2}:[^\n]*\n` accepts any text (or none) after the colon
+    // and tolerates optional `**` markdown bold wrappers on either side.
+    // The checklist group uses `+` (not `*`) so that a bold `**Plans:**` description
+    // line with no immediately-following checklist items (e.g. a summary line above a
+    // separate bare `Plans:` block) does not consume the match and prevent the actual
+    // list from being found.
+    // Review fix (F2): `(?:^|\n)` anchors the match to start-of-line so mid-line
+    // occurrences like `***Plans:***` embedded in a sentence or `OpenPlans: foo`
+    // do not trigger a false match. Groups 1 and 2 retain the same semantics.
+    const plansBlockMatch = phaseSection.match(/(?:^|\n)(\*{0,2}Plans\*{0,2}:[^\n]*\n)((?:\s*-\s*\[[ x]\][^\n]*\n?)+)/i);
     if (!plansBlockMatch) return;
 
     const plansHeader = plansBlockMatch[1];
@@ -563,8 +576,16 @@ function cmdRoadmapAnnotateDependencies(cwd, phaseNum, raw) {
     const linesByWave = new Map();
     for (const line of listLines) {
       // Match plan ID from line: "- [ ] 01-01-PLAN.md — ..." or "- [ ] 01-01: ..."
-      const idMatch = line.match(/\[\s*[x ]\s*\]\s*([\w-]+?)(?:-PLAN\.md|\.md|:|\s—)/i);
+      // #3691 Bug 3: `[\w-]+?` excluded `.`, so decimal IDs like `02.3-01` were captured
+      // as `02` only and never matched planData entries. `[\w.-]+?` preserves the
+      // terminating alternation (`-PLAN.md|.md|:|\s—`) as the boundary anchor.
+      const idMatch = line.match(/\[\s*[x ]\s*\]\s*([\w.-]+?)(?:-PLAN\.md|\.md|:|\s—)/i);
       const planId = idMatch ? idMatch[1] : null;
+      // Review fix (F3): reject malformed IDs that start with `.`, contain consecutive
+      // dots, or otherwise violate the `^\w[\w.-]*$` contract. A leading-dot ID
+      // (e.g. `.invalid-PLAN.md`) would silently default to wave 1 — defensively
+      // skip the line instead so corrupted ROADMAP entries don't corrupt wave layout.
+      if (planId && !/^\w[\w.-]*$/.test(planId)) continue;
       const planEntry = planId ? planData.find(p => p.planId === planId) : null;
       const wave = planEntry ? planEntry.wave : 1;
       if (!linesByWave.has(wave)) linesByWave.set(wave, []);
diff --git a/tests/bug-3691-annotate-deps-plans-block-variants.test.cjs b/tests/bug-3691-annotate-deps-plans-block-variants.test.cjs
new file mode 100644
index 000000000..f6b48e1a5
--- /dev/null
+++ b/tests/bug-3691-annotate-deps-plans-block-variants.test.cjs
@@ -0,0 +1,389 @@
+'use strict';
+
+// allow-test-rule: source-text-is-the-product
+// Reads .md/.json/.yml product files whose deployed text IS what the
+// runtime loads — testing text content tests the deployed contract.
+
+/**
+ * Regression — issue #3691
+ *
+ * Two regex defects fixed in `roadmap.cjs` function `cmdRoadmapAnnotateDependencies`,
+ * plus two review-cycle additions (F3 defensive guard, F4 adversarial gaps):
+ *
+ * Bug 1 (line ~553) — Plans-block detection regex `/(Plans:\s*\n)/i` requires no text
+ *   after the colon. Headers like `Plans: 3 plans across 2 waves\n` or
+ *   `**Plans:** 3 plans\n` are silently skipped and the function early-returns.
+ *   Fix: `(?:^|\n)(\*{0,2}Plans\*{0,2}:[^\n]*\n)` anchors to start-of-line and
+ *   accepts optional bold wrappers and any trailing text on the header line.
+ *
+ * Bug 3 (line ~566) — Plan-ID extraction regex `/([\w-]+?)/` excludes `.`, so
+ *   decimal plan IDs like `02.3-01` are captured as `02` only, never match
+ *   the planData entry, and every plan defaults to wave 1.
+ *   Fix: `[\w.-]+?` includes `.` so decimal IDs are captured in full.
+ *
+ * Note: "Bug 2" (phase-section boundary `\d` → `\d[\d.]*`) was confirmed empirically
+ *   to be a no-op: any phase heading starts with a digit, so `\d` already matches.
+ *   The no-op change was dropped from the PR; this file has no Bug 2 describe block.
+ *
+ * Review additions:
+ *   F3 — Leading-dot plan ID guard: malformed IDs like `.invalid` are rejected
+ *        before planData.find() rather than silently defaulting to wave 1.
+ *   F4 — Adversarial gaps: multi-decimal leading-zero IDs (001.10-PLAN.md) and
+ *        bare-bold `**Plans:**` (no trailing text) are explicitly covered.
+ */
+
+const { test, describe, afterEach } = require('node:test');
+const assert = require('node:assert/strict');
+const fs = require('node:fs');
+const path = require('node:path');
+const { runGsdTools, createTempProject, cleanup } = require('./helpers.cjs');
+
+// ---------------------------------------------------------------------------
+// Shared test helpers
+// ---------------------------------------------------------------------------
+
+function makePlanProject(files = {}) {
+  const dir = createTempProject();
+  fs.mkdirSync(path.join(dir, '.planning', 'phases'), { recursive: true });
+  for (const [rel, content] of Object.entries(files)) {
+    const abs = path.join(dir, rel);
+    fs.mkdirSync(path.dirname(abs), { recursive: true });
+    fs.writeFileSync(abs, content, 'utf-8');
+  }
+  return dir;
+}
+
+/** Build a minimal PLAN.md frontmatter string */
+function makePlan({ phase, plan, wave, dependsOn = [] }) {
+  return [
+    '---',
+    `phase: "${phase}"`,
+    `plan: "${plan}"`,
+    'type: standard',
+    `wave: ${wave}`,
+    `depends_on: [${dependsOn.map(d => `"${d}"`).join(', ')}]`,
+    'files_modified: []',
+    'autonomous: true',
+    'must_haves:',
+    '  truths: []',
+    '  artifacts: []',
+    '  key_links: []',
+    '---',
+    '',
+    `<objective>Plan ${plan}</objective>`,
+    '',
+  ].join('\n');
+}
+
+// ---------------------------------------------------------------------------
+// Bug 1 — Plans-block detection: inline summary text after the colon
+// ---------------------------------------------------------------------------
+
+describe('bug #3691 — Bug 1: Plans-block detection with inline summary', () => {
+  let tmpDir;
+  afterEach(() => cleanup(tmpDir));
+
+  test('Plans: N plans (inline count after colon) is detected as a Plans-block', (t) => {
+    // Pre-fix: `Plans:\s*\n` requires bare newline — fails for "Plans: 2 plans\n"
+    // Post-fix: `Plans:[^\n]*\n` accepts any text after the colon
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      '**Goal:** Set up project',
+      '',
+      'Plans: 2 plans',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 2, dependsOn: ['01-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'Plans-block with inline summary must be detected and written');
+    assert.ok(out.waves >= 1, 'at least one wave must be written');
+
+    const written = fs.readFileSync(path.join(tmpDir, '.planning', 'ROADMAP.md'), 'utf-8');
+    assert.ok(written.includes('Wave'), 'wave annotation must appear in ROADMAP.md');
+  });
+
+  test('Plans: N plans across N waves (longer inline text) is detected', (t) => {
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      'Plans: 3 plans across 2 waves',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '- [ ] 01-03-PLAN.md — Task C',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 1 }),
+      '.planning/phases/01-foundation/01-03-PLAN.md': makePlan({ phase: '1', plan: '01-03', wave: 2, dependsOn: ['01-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'Plans-block with "N plans across N waves" inline text must be detected');
+  });
+
+  test('**Plans:** (bold markdown wrapper) is detected as a Plans-block', (t) => {
+    // Bold wrapper: `**Plans:** 3 plans across 2 waves`
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      '**Plans:** 2 plans',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 2 }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      '**Plans:** bold-wrapped header must be detected as a Plans-block');
+  });
+
+  test('bare Plans: (no inline text, legacy format) still works after fix', (t) => {
+    // Regression guard: the fix must not break the working case
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      'Plans:',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 2 }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'bare Plans: (legacy format) must still be detected after the fix');
+  });
+});
+
+// ---------------------------------------------------------------------------
+// Bug 3 — Plan-ID extraction: decimal phase IDs like 02.3-01
+// ---------------------------------------------------------------------------
+
+describe('bug #3691 — Bug 3: decimal plan IDs (e.g. 02.3-01-PLAN.md) parse correctly', () => {
+  let tmpDir;
+  afterEach(() => cleanup(tmpDir));
+
+  test('decimal plan ID 02.3-01 is captured fully and matched to the correct wave', (t) => {
+    // Pre-fix: `[\w-]+?` stops at `.` → captures `02` only → planData.find misses → wave = 1 for all
+    // Post-fix: `[\w.-]+?` captures `02.3-01` → planData.find resolves → correct wave written
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 02.3: Surgical edit ops',
+      '',
+      'Plans: 2 plans across 2 waves',
+      '- [ ] 02.3-01-PLAN.md — Path resolver',
+      '- [ ] 02.3-02-PLAN.md — Op handlers',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/02.3-surgical-edit-ops/02.3-01-PLAN.md': makePlan({ phase: '02.3', plan: '02.3-01', wave: 1 }),
+      '.planning/phases/02.3-surgical-edit-ops/02.3-02-PLAN.md': makePlan({ phase: '02.3', plan: '02.3-02', wave: 2, dependsOn: ['02.3-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 02.3', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'decimal-phase ROADMAP with inline Plans: summary must be annotated');
+    assert.strictEqual(out.waves, 2,
+      'two distinct waves must be identified (02.3-01→wave 1, 02.3-02→wave 2)');
+
+    const written = fs.readFileSync(path.join(tmpDir, '.planning', 'ROADMAP.md'), 'utf-8');
+    assert.ok(/Wave 1/.test(written), 'Wave 1 header must appear in output');
+    assert.ok(/Wave 2/.test(written), 'Wave 2 header must appear in output');
+  });
+
+  test('combined fixture: decimal phase + bold Plans: header (both bugs together)', (t) => {
+    // Exercises Bug 1 (bold **Plans:** header) AND Bug 3 (decimal IDs) simultaneously.
+    // This is the exact ROADMAP fragment from the issue report.
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '## Milestone v1.2',
+      '',
+      '### Phase 02.3: Surgical edit ops',
+      '',
+      '**Plans:** 3 plans across 2 waves',
+      '- [ ] 02.3-01-PLAN.md — Path resolver',
+      '- [ ] 02.3-02-PLAN.md — Op handlers',
+      '- [ ] 02.3-03-PLAN.md — Tests',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/02.3-surgical-edit-ops/02.3-01-PLAN.md': makePlan({ phase: '02.3', plan: '02.3-01', wave: 1 }),
+      '.planning/phases/02.3-surgical-edit-ops/02.3-02-PLAN.md': makePlan({ phase: '02.3', plan: '02.3-02', wave: 1 }),
+      '.planning/phases/02.3-surgical-edit-ops/02.3-03-PLAN.md': makePlan({ phase: '02.3', plan: '02.3-03', wave: 2, dependsOn: ['02.3-01', '02.3-02'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 02.3', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'combined fixture (bold Plans: + decimal IDs) must produce updated: true');
+    assert.strictEqual(out.waves, 2,
+      'wave 2 dependency must be detected from decimal plan IDs');
+  });
+});
+
+// ---------------------------------------------------------------------------
+// F3 review fix — Leading-dot ID validation guard (defensive, malformed ROADMAP)
+// ---------------------------------------------------------------------------
+
+describe('review fix F3 — leading-dot plan ID is rejected (defensive guard)', () => {
+  let tmpDir;
+  afterEach(() => cleanup(tmpDir));
+
+  test('checklist line with leading-dot plan ID is skipped and does not silently default to wave 1', (t) => {
+    // Guards: `.invalid-PLAN.md` would be captured as `.invalid` by the `[\w.-]+?` regex
+    // (since `.` is now included), which starts with a dot — an invalid ID.
+    // Without the guard, planData.find() misses it and wave defaults to 1, silently
+    // polluting the output. With the guard, the line is skipped entirely.
+    // We verify this by having TWO real plans with known waves (1 and 2), plus one
+    // malformed line. The malformed line must not appear in the wave-annotated output.
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      'Plans: 3 items',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] .invalid-PLAN.md — Corrupted entry',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 2, dependsOn: ['01-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    // Two valid plans resolve to 2 waves — annotation must still proceed
+    assert.strictEqual(out.updated, true, 'annotation must proceed despite malformed line');
+    assert.strictEqual(out.waves, 2, 'two distinct waves from the two valid plans');
+
+    const written = fs.readFileSync(path.join(tmpDir, '.planning', 'ROADMAP.md'), 'utf-8');
+    // The malformed line should not appear in the written output (it was skipped)
+    assert.ok(!written.includes('.invalid-PLAN.md'),
+      'malformed leading-dot entry must be dropped from the annotated output');
+  });
+});
+
+// ---------------------------------------------------------------------------
+// F4 review additions — adversarial test gaps
+// ---------------------------------------------------------------------------
+
+describe('review fix F4 — adversarial test gaps', () => {
+  let tmpDir;
+  afterEach(() => cleanup(tmpDir));
+
+  test('001.10-PLAN.md multi-decimal leading-zero ID is captured fully and wave-assigned correctly', (t) => {
+    // Guards regression of Bug 3: `[\w-]+?` would stop at the first `.` and
+    // capture `001` instead of `001.10`, which never matches any planData entry.
+    // Post-fix `[\w.-]+?` must capture `001.10` in full.
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 001.10: Extended decimal phase',
+      '',
+      'Plans: 2 plans across 2 waves',
+      '- [ ] 001.10-01-PLAN.md — First task',
+      '- [ ] 001.10-02-PLAN.md — Second task',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/001.10-extended/001.10-01-PLAN.md': makePlan({ phase: '001.10', plan: '001.10-01', wave: 1 }),
+      '.planning/phases/001.10-extended/001.10-02-PLAN.md': makePlan({ phase: '001.10', plan: '001.10-02', wave: 2, dependsOn: ['001.10-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 001.10', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      'multi-decimal leading-zero plan ID must be captured fully and annotated');
+    assert.strictEqual(out.waves, 2,
+      'wave 2 dependency must be resolved from full 001.10-02 ID (not truncated to 001)');
+  });
+
+  test('**Plans:** (bold, no trailing text) is matched and checklist is processed', (t) => {
+    // Guards the bare-bold variant: `**Plans:**` with nothing after the colon.
+    // The `[^\n]*` quantifier accepts zero chars so this should already work,
+    // but this test would fail if `\*{0,2}Plans\*{0,2}` regressed to require no stars.
+    const roadmap = [
+      '# Roadmap',
+      '',
+      '### Phase 1: Foundation',
+      '',
+      '**Plans:**',
+      '- [ ] 01-01-PLAN.md — Task A',
+      '- [ ] 01-02-PLAN.md — Task B',
+      '',
+    ].join('\n');
+
+    tmpDir = makePlanProject({
+      '.planning/ROADMAP.md': roadmap,
+      '.planning/phases/01-foundation/01-01-PLAN.md': makePlan({ phase: '1', plan: '01-01', wave: 1 }),
+      '.planning/phases/01-foundation/01-02-PLAN.md': makePlan({ phase: '1', plan: '01-02', wave: 2, dependsOn: ['01-01'] }),
+    });
+
+    const result = runGsdTools('roadmap annotate-dependencies 1', tmpDir);
+    assert.ok(result.success, `Command failed: ${result.error}`);
+    const out = JSON.parse(result.output);
+    assert.strictEqual(out.updated, true,
+      '**Plans:** bare-bold variant (no trailing text) must be detected and annotated');
+    assert.strictEqual(out.waves, 2,
+      'wave assignment must resolve correctly from planData for bare-bold variant');
+  });
+});