diff --git a/tools/enforce-classifier-match.mjs b/tools/enforce-classifier-match.mjs
index d7aaa4e1..f782e6ad 100644
--- a/tools/enforce-classifier-match.mjs
+++ b/tools/enforce-classifier-match.mjs
@@ -40,13 +40,22 @@ function nodeMatches(recommendation, toolUse) {
   if (!recommendation || !toolUse) return false;
   const rec = normalizeNode(recommendation);
   if (!rec) return false;
+  // Hole 5 fix: exact match OR matching last segment after ':' / '#'.
+  // No generic substring (would match meta-planning to planning).
+  const matches = (candidate) => {
+    if (!candidate) return false;
+    if (candidate === rec) return true;
+    const recSegs = rec.split(/[:#]/);
+    const canSegs = candidate.split(/[:#]/);
+    const recLast = recSegs[recSegs.length - 1];
+    const canLast = canSegs[canSegs.length - 1];
+    return recLast === canLast;
+  };
   if (toolUse.name === 'Skill') {
-    const s = normalizeNode(String(toolUse.input && toolUse.input.skill || ''));
-    if (s && (s === rec || s.includes(rec) || rec.includes(s))) return true;
+    return matches(normalizeNode(String(toolUse.input && toolUse.input.skill || '')));
   }
-  if (toolUse.name === 'Task') {
-    const sub = String(toolUse.input && toolUse.input.subagent_type || '').toLowerCase();
-    if (sub && rec.includes(sub)) return true;
+  if (toolUse.name === 'Task' || toolUse.name === 'Agent') {
+    return matches(String(toolUse.input && toolUse.input.subagent_type || '').toLowerCase());
   }
   return false;
 }
diff --git a/tools/enforce-classifier-match.test.mjs b/tools/enforce-classifier-match.test.mjs
index 1a6e90af..fb076224 100644
--- a/tools/enforce-classifier-match.test.mjs
+++ b/tools/enforce-classifier-match.test.mjs
@@ -125,4 +125,35 @@ describe('enforce-classifier-match / decide', () => {
     });
     expect(r.block).toBe(false);
   });
+
+  it('does not match meta-planning to planning recommendation (hole 5)', () => {
+    const r = decide({
+      toolUses: [{ name: 'Skill', input: { skill: 'meta-planning' } }, { name: 'Edit', input: {} }],
+      recommendation: 'planning',
+      confidence: 0.9,
+      assistantText: '',
+      override: null,
+    });
+    expect(r.block).toBe(true);
+  });
+
+  it('matches superpowers:writing-plans to writing-plans recommendation (regression — keep working)', () => {
+    expect(decide({
+      toolUses: [{ name: 'Skill', input: { skill: 'superpowers:writing-plans' } }, { name: 'Edit', input: {} }],
+      recommendation: 'writing-plans',
+      confidence: 0.9,
+      assistantText: '',
+      override: null,
+    }).block).toBe(false);
+  });
+
+  it('matches exact-name skill regression — keep working', () => {
+    expect(decide({
+      toolUses: [{ name: 'Skill', input: { skill: 'brainstorming' } }, { name: 'Edit', input: {} }],
+      recommendation: 'brainstorming',
+      confidence: 0.9,
+      assistantText: '',
+      override: null,
+    }).block).toBe(false);
+  });
 });