diff --git a/src/resources/extensions/gsd/guided-flow.ts b/src/resources/extensions/gsd/guided-flow.ts
index d0f400448..016f5335b 100644
--- a/src/resources/extensions/gsd/guided-flow.ts
+++ b/src/resources/extensions/gsd/guided-flow.ts
@@ -480,7 +480,7 @@ async function buildDiscussSlicePrompt(
   sid: string,
   sTitle: string,
   base: string,
-  options?: { rediscuss?: boolean },
+  options?: { rediscuss?: boolean; structuredQuestionsAvailable?: string },
 ): Promise<string> {
   const inlined: string[] = [];
 
@@ -560,6 +560,7 @@ async function buildDiscussSlicePrompt(
     contextPath: sliceContextPath,
     projectRoot: base,
     inlinedTemplates,
+    structuredQuestionsAvailable: options?.structuredQuestionsAvailable ?? "false",
     commitInstruction: buildDocsCommitInstruction(`docs(${mid}/${sid}): slice context from discuss`),
   });
 }
@@ -801,7 +802,8 @@ export async function showDiscuss(
       if (confirm !== "rediscuss") continue;
     }
 
-    const prompt = await buildDiscussSlicePrompt(mid, chosen.id, chosen.title, basePath, { rediscuss: isRediscuss });
+    const sqAvail = pi.getActiveTools().includes("ask_user_questions") ? "true" : "false";
+    const prompt = await buildDiscussSlicePrompt(mid, chosen.id, chosen.title, basePath, { rediscuss: isRediscuss, structuredQuestionsAvailable: sqAvail });
     await dispatchWorkflow(pi, prompt, "gsd-discuss", ctx, "discuss-slice");
 
     // Wait for the discuss session to finish, then loop back to the picker
@@ -1514,7 +1516,8 @@ export async function showSmartEntry(
         }),
       }), "gsd-run", ctx, "plan-slice");
     } else if (choice === "discuss") {
-      await dispatchWorkflow(pi, await buildDiscussSlicePrompt(milestoneId, sliceId, sliceTitle, basePath, { rediscuss: hasContext }), "gsd-run", ctx, "discuss-slice");
+      const sqAvail = pi.getActiveTools().includes("ask_user_questions") ? "true" : "false";
+      await dispatchWorkflow(pi, await buildDiscussSlicePrompt(milestoneId, sliceId, sliceTitle, basePath, { rediscuss: hasContext, structuredQuestionsAvailable: sqAvail }), "gsd-run", ctx, "discuss-slice");
     } else if (choice === "research") {
       const researchTemplates = inlineTemplate("research", "Research");
       await dispatchWorkflow(pi, loadPrompt("guided-research-slice", {
diff --git a/src/resources/extensions/gsd/prompts/guided-discuss-slice.md b/src/resources/extensions/gsd/prompts/guided-discuss-slice.md
index 63ec13fb7..353c5f831 100644
--- a/src/resources/extensions/gsd/prompts/guided-discuss-slice.md
+++ b/src/resources/extensions/gsd/prompts/guided-discuss-slice.md
@@ -22,7 +22,9 @@ Do **not** go deep — just enough that your questions reflect what's actually t
 
 ### Question rounds
 
-Ask **1–3 questions per round** using `ask_user_questions`. **Call `ask_user_questions` exactly once per turn — never make multiple calls with the same or overlapping questions. Wait for the user's response before asking the next round.** Keep each question focused on one of:
+**If `{{structuredQuestionsAvailable}}` is `true`:** Ask **1–3 questions per round** using `ask_user_questions`. **Call `ask_user_questions` exactly once per turn — never make multiple calls with the same or overlapping questions. Wait for the user's response before asking the next round.**
+**If `{{structuredQuestionsAvailable}}` is `false`:** Ask **1–3 questions per round** in plain text. Number them and wait for the user's response before asking the next round.
+Keep each question focused on one of:
 - **UX and user-facing behaviour** — what does the user see, click, trigger, or experience?
 - **Edge cases and failure states** — what happens when things go wrong or are in unusual states?
 - **Scope boundaries** — what is explicitly in vs out for this slice? What deferred to later?
@@ -37,9 +39,7 @@ After each round of answers, decide whether you already have enough signal to wr
 - **Incremental persistence:** After every 2 question rounds, silently save a draft `{{sliceId}}-CONTEXT-DRAFT.md` in `{{sliceDirPath}}` using `gsd_summary_save` with `milestone_id: {{milestoneId}}`, `slice_id: {{sliceId}}`, `artifact_type: "CONTEXT-DRAFT"`. This protects against session crashes losing confirmed work. Do NOT mention this to the user. The final context file will replace it.
 - If not, investigate any new unknowns and continue to the next round immediately. Do **not** ask a meta "ready to wrap up?" question after every round.
 - Ask a single wrap-up question only when you genuinely believe the slice is well understood or the user signals they want to stop.
-- When you do ask it, use `ask_user_questions` with:
-  - "Write the context file" *(recommended when the slice is well understood)*
-  - "One more pass"
+- When you do ask it, offer two choices: "Write the context file" *(recommended when the slice is well understood)* or "One more pass". Use `ask_user_questions` if available, otherwise ask in plain text.
 
 ---
 
diff --git a/src/resources/extensions/gsd/tests/discuss-slice-structured-questions.test.ts b/src/resources/extensions/gsd/tests/discuss-slice-structured-questions.test.ts
new file mode 100644
index 000000000..a52114df6
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/discuss-slice-structured-questions.test.ts
@@ -0,0 +1,46 @@
+/**
+ * Regression test for discuss-slice structured questions availability
+ *
+ * The guided-discuss-slice.md template must use the structuredQuestionsAvailable
+ * template variable to conditionally switch between ask_user_questions tool
+ * calls and plain-text questions, so the prompt works correctly when the
+ * structured questions tool is not available.
+ */
+
+import { describe, it } from 'node:test'
+import assert from 'node:assert/strict'
+import { readFileSync } from 'node:fs'
+import { resolve } from 'node:path'
+
+const template = readFileSync(
+  resolve(process.cwd(), 'src', 'resources', 'extensions', 'gsd', 'prompts', 'guided-discuss-slice.md'),
+  'utf-8',
+)
+
+describe('discuss-slice structuredQuestionsAvailable template variable', () => {
+  it('template references structuredQuestionsAvailable variable', () => {
+    assert.ok(
+      template.includes('{{structuredQuestionsAvailable}}'),
+      'guided-discuss-slice.md must use {{structuredQuestionsAvailable}} template variable',
+    )
+  })
+
+  it('template handles both true and false cases', () => {
+    const trueCase = template.includes('`{{structuredQuestionsAvailable}}` is `true`')
+    const falseCase = template.includes('`{{structuredQuestionsAvailable}}` is `false`')
+
+    assert.ok(trueCase, 'template must have a branch for structuredQuestionsAvailable=true')
+    assert.ok(falseCase, 'template must have a branch for structuredQuestionsAvailable=false')
+  })
+
+  it('false case instructs plain text questions', () => {
+    const falseIdx = template.indexOf('`{{structuredQuestionsAvailable}}` is `false`')
+    assert.ok(falseIdx !== -1)
+
+    const afterFalse = template.slice(falseIdx, falseIdx + 300)
+    assert.ok(
+      afterFalse.includes('plain text'),
+      'when structuredQuestionsAvailable is false, questions should be in plain text',
+    )
+  })
+})