diff --git a/src/askpass.test.ts b/src/askpass.test.ts
index 2f744bb..70d2fb3 100644
--- a/src/askpass.test.ts
+++ b/src/askpass.test.ts
@@ -8,7 +8,10 @@ import { AskpassBridge } from "./askpass";
 
 const run = promisify(execFile);
 let bridge: AskpassBridge | undefined;
-afterEach(() => bridge?.stop());
+afterEach(async () => {
+  bridge?.stop();
+  bridge = undefined;
+});
 
 test("helper script round-trips a prompt to onPrompt and returns the answer", async () => {
   const dir = mkdtempSync(join(tmpdir(), "jp-ask-"));
@@ -23,3 +26,58 @@ test("helper script round-trips a prompt to onPrompt and returns the answer", as
   expect(stdout.trim()).toBe("s3cret");
   rmSync(dir, { recursive: true, force: true });
 });
+
+test("onPrompt rejection: helper process completes promptly and returns empty answer", async () => {
+  const dir = mkdtempSync(join(tmpdir(), "jp-ask-reject-"));
+  bridge = new AskpassBridge({
+    dir,
+    onPrompt: async (_p) => { throw new Error("user cancelled"); },
+  });
+  const env = await bridge.start();
+
+  // The helper must exit within 3 seconds; if it hangs the test times out with a clear error.
+  const result = await Promise.race([
+    run(env.GIT_ASKPASS, ["Password:"], {
+      env: { ...process.env, JEKYLL_ASKPASS_SOCK: env.JEKYLL_ASKPASS_SOCK },
+    }).then(({ stdout }) => ({ timedOut: false, stdout }))
+      .catch(() => ({ timedOut: false, stdout: "" })),
+    new Promise<{ timedOut: true; stdout: string }>((resolve) =>
+      setTimeout(() => resolve({ timedOut: true, stdout: "" }), 3000)
+    ),
+  ]);
+
+  expect(result.timedOut, "helper process hung instead of exiting promptly").toBe(false);
+  // Empty answer is fine — git will fail fast on its own
+  expect(result.stdout.trim()).toBe("");
+  rmSync(dir, { recursive: true, force: true });
+});
+
+test("restart on same dir: stop() then start() again succeeds with no EADDRINUSE", async () => {
+  const dir = mkdtempSync(join(tmpdir(), "jp-ask-restart-"));
+
+  // First session
+  bridge = new AskpassBridge({
+    dir,
+    onPrompt: async (p) => (p.includes("user") ? "bob" : "pass1"),
+  });
+  const env1 = await bridge.start();
+  const { stdout: out1 } = await run(env1.GIT_ASKPASS, ["username:"], {
+    env: { ...process.env, JEKYLL_ASKPASS_SOCK: env1.JEKYLL_ASKPASS_SOCK },
+  });
+  expect(out1.trim()).toBe("bob");
+  bridge.stop();
+  bridge = undefined;
+
+  // Second session — same dir; must not throw EADDRINUSE
+  bridge = new AskpassBridge({
+    dir,
+    onPrompt: async (p) => (p.includes("Password") ? "newpass" : "carol"),
+  });
+  const env2 = await bridge.start();
+  const { stdout: out2 } = await run(env2.GIT_ASKPASS, ["Password for 'https://y':"], {
+    env: { ...process.env, JEKYLL_ASKPASS_SOCK: env2.JEKYLL_ASKPASS_SOCK },
+  });
+  expect(out2.trim()).toBe("newpass");
+
+  rmSync(dir, { recursive: true, force: true });
+});
diff --git a/src/askpass.ts b/src/askpass.ts
index 128d85f..c498e20 100644
--- a/src/askpass.ts
+++ b/src/askpass.ts
@@ -1,5 +1,5 @@
 import { createServer, Server } from "node:net";
-import { chmodSync, writeFileSync } from "node:fs";
+import { chmodSync, unlinkSync, writeFileSync } from "node:fs";
 import { join } from "node:path";
 
 export class AskpassBridge {
@@ -18,15 +18,34 @@ export class AskpassBridge {
     this.sock = join(this.opts.dir, "askpass.sock");
     this.script = join(this.opts.dir, "askpass.sh");
 
+    // Best-effort removal of a stale socket from a previous unclean shutdown.
+    try { unlinkSync(this.sock); } catch { /* ignore ENOENT */ }
+
     this.server = createServer({ allowHalfOpen: true }, (conn) => {
       let buf = "";
       conn.on("data", (d) => (buf += d.toString()));
-      conn.on("end", async () => {
-        const answer = await this.opts.onPrompt(buf.replace(/\n$/, ""));
-        conn.end(answer.endsWith("\n") ? answer : answer + "\n");
+      conn.on("end", () => {
+        // Wrap onPrompt in try/catch so a rejection never hangs the git/ssh process.
+        this.opts.onPrompt(buf.replace(/\n$/, "")).then(
+          (answer) => {
+            conn.end(answer.endsWith("\n") ? answer : answer + "\n");
+          },
+          (_err) => {
+            // User cancelled or onPrompt threw — send empty reply so git fails fast.
+            conn.end("\n");
+          }
+        );
+      });
+    });
+
+    // Fix: reject the promise on listen error (e.g. EADDRINUSE) instead of hanging.
+    await new Promise<void>((res, rej) => {
+      this.server!.once("error", rej);
+      this.server!.listen(this.sock, () => {
+        this.server!.removeListener("error", rej);
+        res();
       });
     });
-    await new Promise<void>((res) => this.server!.listen(this.sock, res));
 
     // Helper: send argv[1] (the prompt) to the socket, print the reply.
     // Uses a Node one-liner for reliable EOF signalling across platforms
@@ -56,5 +75,8 @@ export class AskpassBridge {
   stop(): void {
     this.server?.close();
     this.server = undefined;
+    // Clean up socket and helper script to prevent stale-socket EADDRINUSE on restart.
+    try { unlinkSync(this.sock); } catch { /* ignore ENOENT */ }
+    try { unlinkSync(this.script); } catch { /* ignore ENOENT */ }
   }
 }