diff --git a/test/helpers/e2e-helpers.test.ts b/test/helpers/e2e-helpers.test.ts
index 47701a6e9..0dc1b8ce0 100644
--- a/test/helpers/e2e-helpers.test.ts
+++ b/test/helpers/e2e-helpers.test.ts
@@ -62,6 +62,22 @@ describe('matchesUnnegated', () => {
     )).toBe(false);
   });
 
+  test('recognizes "-n\'t" contractions generically (can\'t, won\'t, aren\'t, hasn\'t)', () => {
+    // A bare `\b n't \b` alternative can never match mid-word (no word
+    // boundary between the letters immediately before "n" and "n" itself),
+    // so only the contractions spelled out explicitly ever matched. Verify
+    // the generic [a-z]+n't pattern actually catches the common ones that
+    // previously fell through silently.
+    expect(matchesUnnegated("This can't promote the payload into columns.", splitPattern)).toBe(false);
+    expect(matchesUnnegated("This won't promote the payload into columns.", splitPattern)).toBe(false);
+    expect(matchesUnnegated("These aren't reasons to promote the payload into columns.", splitPattern)).toBe(false);
+    expect(matchesUnnegated("It hasn't been decided to promote the payload into columns.", splitPattern)).toBe(false);
+  });
+
+  test('recognizes "cannot" as a negation', () => {
+    expect(matchesUnnegated('This cannot promote the payload into columns.', splitPattern)).toBe(false);
+  });
+
   test('catches a positive match even when an unrelated negation appears earlier in the text', () => {
     expect(matchesUnnegated(
       'This is not a JSONField concern. Separately, I recommend you promote the payload into explicit columns.',
diff --git a/test/helpers/e2e-helpers.ts b/test/helpers/e2e-helpers.ts
index e09e6b352..b0187c2c0 100644
--- a/test/helpers/e2e-helpers.ts
+++ b/test/helpers/e2e-helpers.ts
@@ -156,7 +156,12 @@ export function matchesUnnegated(text: string, pattern: RegExp): boolean {
   // to the model RATHER THAN create a separate table") — the rejected
   // alternative can otherwise match the pattern just as strongly as a real
   // recommendation would, with no single negation word anywhere near it.
-  const NEGATION = /\b(not|n't|no|never|don't|doesn't|didn't|shouldn't|wouldn't|isn't|without|against|rather than|instead of)\b/i;
+  // [a-z]+n't matches any "-n't" contraction generically (can't, won't,
+  // aren't, hasn't, doesn't, don't, wouldn't, ...) — a bare `\b n't \b`
+  // alternative can never match mid-word (there's no word boundary between
+  // the letters immediately before "n" and "n" itself), so it silently
+  // covered nothing beyond the contractions already spelled out explicitly.
+  const NEGATION = /\b(not|no|never|cannot|without|against|rather than|instead of)\b|[a-z]+n't\b/i;
   const flags = pattern.flags.includes('g') ? pattern.flags : pattern.flags + 'g';
   const re = new RegExp(pattern.source, flags);
   let m: RegExpExecArray | null;
diff --git a/test/skill-e2e-plan.test.ts b/test/skill-e2e-plan.test.ts
index 1a4dbb7f7..4004b6197 100644
--- a/test/skill-e2e-plan.test.ts
+++ b/test/skill-e2e-plan.test.ts
@@ -456,12 +456,16 @@ Focus specifically on the data model design in the plan. Apply the data model re
     // assumptions below.
     const lower = review.toLowerCase();
     const unformatted = review.replace(/[`*_]/g, '');
+    // matchesUnnegated so a (would-be-regression) "I would NOT recommend a
+    // separate tier model here" answer doesn't get counted as a pass just
+    // for containing the words — consistent with the sibling counterexample
+    // tests below.
     const recommendsSeparateModel =
-      /separate\s+(subscription\s*)?tier\s*model/i.test(unformatted) ||
-      /new\s+(subscription\s*)?tier\s*model/i.test(unformatted) ||
-      /subscriptiontier\s*model/i.test(unformatted) ||
-      /extract[\s\S]*tier[\s\S]*model/i.test(unformatted) ||
-      /tier\s*(?:table|model)\s*(?:with|per)/i.test(unformatted);
+      matchesUnnegated(unformatted, /separate\s+(subscription\s*)?tier\s*model/i) ||
+      matchesUnnegated(unformatted, /new\s+(subscription\s*)?tier\s*model/i) ||
+      matchesUnnegated(unformatted, /subscriptiontier\s*model/i) ||
+      matchesUnnegated(unformatted, /extract[\s\S]*tier[\s\S]*model/i) ||
+      matchesUnnegated(unformatted, /tier\s*(?:table|model)\s*(?:with|per)/i);
     const pushesBackOnJsonField =
       lower.includes('jsonfield') &&
       (lower.includes('feature') || lower.includes('polymorph') || lower.includes('explicit'));