diff --git a/src/resources/extensions/ask-user-questions.ts b/src/resources/extensions/ask-user-questions.ts
index 19f8746cd..380c86bfe 100644
--- a/src/resources/extensions/ask-user-questions.ts
+++ b/src/resources/extensions/ask-user-questions.ts
@@ -75,7 +75,9 @@ const AskUserQuestionsParams = Type.Object({
 // ─── Per-turn deduplication ──────────────────────────────────────────────────
 // Prevents duplicate question dispatches (especially to remote channels like
 // Discord) when the LLM calls ask_user_questions multiple times with the same
-// questions in a single turn. Keyed by sorted question IDs.
+// questions in a single turn. Keyed by full canonicalized payload (id, header,
+// question, options, allowMultiple) — not just IDs — so that calls with the
+// same IDs but different text/options are treated as distinct.
 
 import { createHash } from "node:crypto";
 
@@ -86,9 +88,18 @@ interface CachedResult {
 
 const turnCache = new Map<string, CachedResult>();
 
-function questionSignature(questions: Array<{ id: string }>): string {
-	const ids = questions.map((q) => q.id).sort().join("|");
-	return createHash("sha256").update(ids).digest("hex").slice(0, 16);
+/** @internal Exported for testing only. */
+export function questionSignature(questions: Question[]): string {
+	const canonical = questions
+		.map((q) => ({
+			id: q.id,
+			header: q.header,
+			question: q.question,
+			options: (q.options || []).map((o) => ({ label: o.label, description: o.description })),
+			allowMultiple: !!q.allowMultiple,
+		}))
+		.sort((a, b) => a.id.localeCompare(b.id));
+	return createHash("sha256").update(JSON.stringify(canonical)).digest("hex").slice(0, 16);
 }
 
 /** Reset the dedup cache. Called on session boundaries. */
diff --git a/src/resources/extensions/gsd/tests/ask-user-questions-dedup.test.ts b/src/resources/extensions/gsd/tests/ask-user-questions-dedup.test.ts
index 98c9e35f7..40276f33c 100644
--- a/src/resources/extensions/gsd/tests/ask-user-questions-dedup.test.ts
+++ b/src/resources/extensions/gsd/tests/ask-user-questions-dedup.test.ts
@@ -17,6 +17,7 @@ import {
 } from "../bootstrap/tool-call-loop-guard.ts";
 import {
   resetAskUserQuestionsCache,
+  questionSignature,
 } from "../../ask-user-questions.ts";
 
 // ═══════════════════════════════════════════════════════════════════════════
@@ -68,4 +69,52 @@ describe("ask_user_questions dedup", () => {
     resetAskUserQuestionsCache();
     // No error means the cache module is properly exported and functional
   });
+
+  // ═══════════════════════════════════════════════════════════════════════════
+  // questionSignature: full-payload hashing prevents stale cache hits
+  // ═══════════════════════════════════════════════════════════════════════════
+
+  test("same IDs with different question text produce different signatures", () => {
+    const q1 = [{ id: "scope", header: "Scope", question: "Which apps to cover?",
+      options: [{ label: "All", description: "Everything" }] }];
+    const q2 = [{ id: "scope", header: "Scope", question: "Which services to test?",
+      options: [{ label: "All", description: "Everything" }] }];
+
+    assert.notEqual(questionSignature(q1), questionSignature(q2),
+      "Different question text with same ID must produce different signatures");
+  });
+
+  test("same IDs with different options produce different signatures", () => {
+    const q1 = [{ id: "scope", header: "Scope", question: "Pick one",
+      options: [{ label: "A", description: "Option A" }] }];
+    const q2 = [{ id: "scope", header: "Scope", question: "Pick one",
+      options: [{ label: "B", description: "Option B" }] }];
+
+    assert.notEqual(questionSignature(q1), questionSignature(q2),
+      "Different options with same ID must produce different signatures");
+  });
+
+  test("identical payloads in different order produce same signature", () => {
+    const q1 = [
+      { id: "b", header: "B", question: "Q2", options: [{ label: "X", description: "x" }] },
+      { id: "a", header: "A", question: "Q1", options: [{ label: "Y", description: "y" }] },
+    ];
+    const q2 = [
+      { id: "a", header: "A", question: "Q1", options: [{ label: "Y", description: "y" }] },
+      { id: "b", header: "B", question: "Q2", options: [{ label: "X", description: "x" }] },
+    ];
+
+    assert.equal(questionSignature(q1), questionSignature(q2),
+      "Same questions in different order must produce the same signature");
+  });
+
+  test("allowMultiple difference produces different signature", () => {
+    const q1 = [{ id: "scope", header: "Scope", question: "Pick",
+      options: [{ label: "A", description: "a" }], allowMultiple: false }];
+    const q2 = [{ id: "scope", header: "Scope", question: "Pick",
+      options: [{ label: "A", description: "a" }], allowMultiple: true }];
+
+    assert.notEqual(questionSignature(q1), questionSignature(q2),
+      "allowMultiple difference must produce different signatures");
+  });
 });