diff --git a/src/resources/extensions/gsd/guided-flow.ts b/src/resources/extensions/gsd/guided-flow.ts
index c57eb4aea..b70fd3fd9 100644
--- a/src/resources/extensions/gsd/guided-flow.ts
+++ b/src/resources/extensions/gsd/guided-flow.ts
@@ -544,12 +544,12 @@ export async function showDiscuss(
       const seed = draftContent
         ? `${basePrompt}\n\n## Prior Discussion (Draft Seed)\n\n${draftContent}`
         : basePrompt;
-      pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: true };
+      pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: false };
       await dispatchWorkflow(pi, seed, "gsd-discuss", ctx, "plan-milestone");
     } else if (choice === "discuss_fresh") {
       const discussMilestoneTemplates = inlineTemplate("context", "Context");
       const structuredQuestionsAvailable = pi.getActiveTools().includes("ask_user_questions") ? "true" : "false";
-      pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: true };
+      pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: false };
       await dispatchWorkflow(pi, loadPrompt("guided-discuss-milestone", {
         milestoneId: mid, milestoneTitle, inlinedTemplates: discussMilestoneTemplates, structuredQuestionsAvailable,
         commitInstruction: buildDocsCommitInstruction(`docs(${mid}): milestone context from discuss`),
diff --git a/src/resources/extensions/gsd/interrupted-session.ts b/src/resources/extensions/gsd/interrupted-session.ts
index dca5f9392..7d391b4cd 100644
--- a/src/resources/extensions/gsd/interrupted-session.ts
+++ b/src/resources/extensions/gsd/interrupted-session.ts
@@ -74,6 +74,7 @@ export async function assessInterruptedSession(
   basePath: string,
 ): Promise<InterruptedSessionAssessment> {
   const pausedSession = readPausedSessionMetadata(basePath);
+  const assessmentBasePath = pausedSession?.worktreePath || basePath;
   const rawLock = readCrashLock(basePath);
   const lock = rawLock && rawLock.pid !== process.pid ? rawLock : null;
 
@@ -108,22 +109,22 @@ export async function assessInterruptedSession(
   }
 
   const isBootstrapCrash = isBootstrapCrashLock(lock);
-  const state = await deriveState(basePath);
+  const state = await deriveState(assessmentBasePath);
   const hasResumableDiskState = hasResumableDerivedState(state);
   const artifactSatisfied = !!(
     lock &&
     !isBootstrapCrash &&
-    verifyExpectedArtifact(lock.unitType, lock.unitId, basePath)
+    verifyExpectedArtifact(lock.unitType, lock.unitId, assessmentBasePath)
   );
 
   let recovery: RecoveryBriefing | null = null;
   if (lock && !isBootstrapCrash && !artifactSatisfied) {
     recovery = synthesizeCrashRecovery(
-      basePath,
+      assessmentBasePath,
       lock.unitType,
       lock.unitId,
       lock.sessionFile,
-      join(gsdRoot(basePath), "activity"),
+      join(gsdRoot(assessmentBasePath), "activity"),
     );
   }
 
diff --git a/src/resources/extensions/gsd/tests/crash-recovery.test.ts b/src/resources/extensions/gsd/tests/crash-recovery.test.ts
index 1ae8e2fb3..132dbec9b 100644
--- a/src/resources/extensions/gsd/tests/crash-recovery.test.ts
+++ b/src/resources/extensions/gsd/tests/crash-recovery.test.ts
@@ -98,12 +98,17 @@ function writeCompleteMilestoneSummary(base: string): void {
   writeFileSync(join(milestoneDir, "M001-SUMMARY.md"), "# Milestone Summary\nDone.\n", "utf-8");
 }
 
-function writePausedSession(base: string, milestoneId = "M001", stepMode = false): void {
+function writePausedSession(
+  base: string,
+  milestoneId = "M001",
+  stepMode = false,
+  worktreePath?: string,
+): void {
   const runtimeDir = join(base, ".gsd", "runtime");
   mkdirSync(runtimeDir, { recursive: true });
   writeFileSync(
     join(runtimeDir, "paused-session.json"),
-    JSON.stringify({ milestoneId, originalBasePath: base, stepMode }, null, 2),
+    JSON.stringify({ milestoneId, originalBasePath: base, stepMode, worktreePath }, null, 2),
     "utf-8",
   );
 }
@@ -227,6 +232,24 @@ test("assessInterruptedSession marks stale paused-session metadata as stale when
   }
 });
 
+test("assessInterruptedSession prefers paused worktree state when worktreePath is recorded", async () => {
+  const base = makeTmpBase();
+  const worktree = join(base, "worktree-copy");
+  try {
+    writeRoadmap(base, false);
+    writeRoadmap(worktree, true);
+    writeCompleteSliceArtifacts(worktree);
+    writeCompleteMilestoneSummary(worktree);
+    writePausedSession(base, "M001", false, worktree);
+
+    const assessment = await assessInterruptedSession(base);
+    assert.equal(assessment.classification, "stale");
+    assert.equal(assessment.hasResumableDiskState, false);
+  } finally {
+    cleanup(base);
+  }
+});
+
 test("assessInterruptedSession keeps unfinished derived state recoverable without trace", async () => {
   const base = makeTmpBase();
   try {
diff --git a/src/resources/extensions/gsd/tests/interrupted-session-ui.test.ts b/src/resources/extensions/gsd/tests/interrupted-session-ui.test.ts
index 67617b721..6a2d0f39d 100644
--- a/src/resources/extensions/gsd/tests/interrupted-session-ui.test.ts
+++ b/src/resources/extensions/gsd/tests/interrupted-session-ui.test.ts
@@ -127,12 +127,12 @@ test("guided-flow stale paused-session scenario is suppressed when no resumable
   }
 });
 
-test("guided-flow source uses step-aware resume label, step-aware discuss handoff, and stale paused cleanup", () => {
+test("guided-flow source uses step-aware resume and clears stale paused metadata without changing discuss handoff semantics", () => {
   const source = readFileSync(join(import.meta.dirname, "..", "guided-flow.ts"), "utf-8");
   assert.ok(source.includes('const interrupted = await assessInterruptedSession(basePath);'));
   assert.ok(source.includes('resumeLabel = interrupted.pausedSession?.stepMode'));
   assert.ok(source.includes('step: interrupted.pausedSession?.stepMode ?? false'));
   assert.ok(source.includes('unlinkSync(join(gsdRoot(basePath), "runtime", "paused-session.json"))'));
-  assert.ok(source.includes('pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: true };'));
+  assert.ok(source.includes('pendingAutoStart = { ctx, pi, basePath, milestoneId: mid, step: false };'));
   assert.ok(source.includes('pendingAutoStart = { ctx, pi, basePath, milestoneId: nextId, step: true };'));
 });