From cd87c9937d085496a4ca03a221f263c592647136 Mon Sep 17 00:00:00 2001
From: Tibsfox <tibsfox@tibsfox.com>
Date: Sun, 5 Apr 2026 11:00:09 -0700
Subject: [PATCH 1/2] fix(gsd): treat zero-slice roadmap as pre-planning in
 guided flow

---
 src/resources/extensions/gsd/guided-flow.ts | 14 +++++++++++++-
 1 file changed, 13 insertions(+), 1 deletion(-)

diff --git a/src/resources/extensions/gsd/guided-flow.ts b/src/resources/extensions/gsd/guided-flow.ts
index d0f400448..6d924d9ac 100644
--- a/src/resources/extensions/gsd/guided-flow.ts
+++ b/src/resources/extensions/gsd/guided-flow.ts
@@ -1314,7 +1314,19 @@ export async function showSmartEntry(
     const roadmapFile = resolveMilestoneFile(basePath, milestoneId, "ROADMAP");
     const hasRoadmap = !!(roadmapFile && await loadFile(roadmapFile));
 
-    if (!hasRoadmap) {
+    // A roadmap file with zero parseable slices (placeholder text) should be
+    // treated the same as no roadmap — offer "Create roadmap" instead of "Go auto"
+    // which would immediately get stuck in blocked state (#3441).
+    let roadmapHasSlices = false;
+    if (hasRoadmap) {
+      const roadmapContent = await loadFile(roadmapFile!);
+      if (roadmapContent) {
+        const parsed = parseRoadmapSlices(roadmapContent);
+        roadmapHasSlices = parsed.length > 0;
+      }
+    }
+
+    if (!hasRoadmap || !roadmapHasSlices) {
       // No roadmap → discuss or plan
       const contextFile = resolveMilestoneFile(basePath, milestoneId, "CONTEXT");
       const hasContext = !!(contextFile && await loadFile(contextFile));

From 5b6d7784c2428989652cc39bca007fca7c118421 Mon Sep 17 00:00:00 2001
From: Tibsfox <tibsfox@tibsfox.com>
Date: Sun, 5 Apr 2026 11:55:49 -0700
Subject: [PATCH 2/2] test(gsd): add zero-slice roadmap guided flow test

---
 .../tests/zero-slice-roadmap-guided.test.ts   | 19 +++++++++++++++++++
 1 file changed, 19 insertions(+)
 create mode 100644 src/resources/extensions/gsd/tests/zero-slice-roadmap-guided.test.ts

diff --git a/src/resources/extensions/gsd/tests/zero-slice-roadmap-guided.test.ts b/src/resources/extensions/gsd/tests/zero-slice-roadmap-guided.test.ts
new file mode 100644
index 000000000..f41b8bd51
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/zero-slice-roadmap-guided.test.ts
@@ -0,0 +1,19 @@
+/**
+ * Regression test for #3441: guided flow must treat a roadmap with zero
+ * parseable slices the same as no roadmap — offer "Create roadmap" not "Go auto".
+ */
+import { test } from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync } from "node:fs";
+import { join } from "node:path";
+
+test("guided-flow checks roadmap slice count before offering auto (#3441)", () => {
+  const src = readFileSync(
+    join(import.meta.dirname, "..", "guided-flow.ts"),
+    "utf-8",
+  );
+  assert.ok(
+    src.includes("roadmapHasSlices") || src.includes("parseRoadmapSlices"),
+    "Guided flow must parse roadmap for slices before deciding which options to show",
+  );
+});