diff --git a/src/resources/extensions/gsd/tests/clear-stale-autostart.test.ts b/src/resources/extensions/gsd/tests/clear-stale-autostart.test.ts
new file mode 100644
index 000000000..c5452e6a6
--- /dev/null
+++ b/src/resources/extensions/gsd/tests/clear-stale-autostart.test.ts
@@ -0,0 +1,41 @@
+/**
+ * clear-stale-autostart.test.ts — #3667
+ *
+ * Verify that guided-flow.ts adds a createdAt timestamp to pending auto-start
+ * entries and implements a staleness check (30s age guard) so that /clear
+ * interrupted discussions don't permanently block future /gsd invocations.
+ */
+
+import { describe, test } from "node:test";
+import assert from "node:assert/strict";
+import { readFileSync } from "node:fs";
+import { join, dirname } from "node:path";
+import { fileURLToPath } from "node:url";
+
+const __dirname = dirname(fileURLToPath(import.meta.url));
+const sourceFile = join(__dirname, "..", "guided-flow.ts");
+
+describe("clear stale pending auto-start (#3667)", () => {
+  const source = readFileSync(sourceFile, "utf-8");
+
+  test("PendingAutoStartEntry interface includes createdAt field", () => {
+    assert.match(source, /createdAt:\s*number/);
+  });
+
+  test("setPendingAutoStart defaults createdAt to Date.now()", () => {
+    assert.match(source, /createdAt:\s*Date\.now\(\)/);
+  });
+
+  test("staleness check uses 30_000ms threshold", () => {
+    assert.match(source, /30[_]?000/);
+  });
+
+  test("stale entry detection checks manifest and context files", () => {
+    assert.match(source, /DISCUSSION-MANIFEST\.json/);
+    assert.match(source, /CONTEXT\.md/);
+  });
+
+  test("stale entries are deleted from the map", () => {
+    assert.match(source, /pendingAutoStartMap\.delete\(basePath\)/);
+  });
+});