From 842e98c070809f2ee0c8d847862b4c697e064d9f Mon Sep 17 00:00:00 2001
From: Alin <41188223+al0x99@users.noreply.github.com>
Date: Sun, 11 Oct 2026 04:20:17 +0200
Subject: [PATCH] Preserve uncertain delivery when timeout messages are
 read-only

---
 .changeset/preserve-send-timeout.md |  5 +++
 src/core/gateway.js                 | 16 ++++-----
 test/gateway-send.test.js           | 55 +++++++++++++++++++++++++++++
 3 files changed, 68 insertions(+), 8 deletions(-)
 create mode 100644 .changeset/preserve-send-timeout.md

diff --git a/.changeset/preserve-send-timeout.md b/.changeset/preserve-send-timeout.md
new file mode 100644
index 0000000..1e5571f
--- /dev/null
+++ b/.changeset/preserve-send-timeout.md
@@ -0,0 +1,5 @@
+---
+"grok-bot-cli": patch
+---
+
+Preserve unknown delivery and the target when a prompt send times out with a DOMException. Keep the original exception as the annotated error's cause.
diff --git a/src/core/gateway.js b/src/core/gateway.js
index dcc9721..21c8157 100644
--- a/src/core/gateway.js
+++ b/src/core/gateway.js
@@ -448,14 +448,14 @@ export async function sendPrompt(session, ref, prompt, extra = {}) {
   } catch (err) {
     // Delivery states: the server answered no (rejected) vs the request may have landed (unknown).
     // Never retry an unknown delivery blindly; read the thread first.
-    if (err && err.delivery == null) {
-      err.delivery = err instanceof GatewayError && err.status != null && err.status < 500 ? "rejected" : "unknown";
-    }
-    if (err && err.targetId == null) err.targetId = rec.id;
-    if (err && err.delivery === "unknown" && err instanceof Error && !/delivery unknown/.test(err.message)) {
-      err.message += " (delivery unknown; check the thread before resending)";
-    }
-    throw err;
+    const delivery = err?.delivery ?? (err instanceof GatewayError && err.status != null && err.status < 500 ? "rejected" : "unknown");
+    const error = delivery === "unknown" && err instanceof Error && !/delivery unknown/.test(err.message)
+      ? Object.assign(new Error(err.message, { cause: err }), err, { name: err.name })
+      : err;
+    if (error && error.delivery == null) error.delivery = delivery;
+    if (error && error.targetId == null) error.targetId = rec.id;
+    if (error !== err) error.message += " (delivery unknown; check the thread before resending)";
+    throw error;
   }
   const messageId = data && typeof data === "object" && typeof data.messageId === "string" ? data.messageId : null;
   // Only a confirmed receipt counts as accepted; anything else is unknown, never a silent accept.
diff --git a/test/gateway-send.test.js b/test/gateway-send.test.js
index fc0a0c9..ff1396c 100644
--- a/test/gateway-send.test.js
+++ b/test/gateway-send.test.js
@@ -73,6 +73,38 @@ test("sendPrompt rejects on a 4xx and preserves the target id", async (t) => {
   });
 });
 
+test("sendPrompt rejects a cancelled preflight without fetching", async (t) => {
+  const controller = new AbortController();
+  controller.abort();
+  let received = 0;
+  t.mock.method(globalThis, "fetch", async () => {
+    received++;
+    throw new Error("Unexpected request after cancellation");
+  });
+  await assert.rejects(sendPrompt(session, "General", "hi", { signal: controller.signal }), (error) => {
+    assert.equal(error.delivery, "rejected");
+    assert.equal(error.reason, "cancelled");
+    return true;
+  });
+  assert.equal(received, 0);
+});
+
+test("sendPrompt preserves a resolution error before prompt transmission", async (t) => {
+  const failure = new DOMException("The operation was aborted due to timeout", "TimeoutError");
+  const original = Object.getOwnPropertyDescriptors(failure);
+  const received = [];
+  t.mock.method(globalThis, "fetch", async (url) => {
+    received.push(new URL(url).pathname);
+    throw failure;
+  });
+  await assert.rejects(sendPrompt(session, "General", "hi"), (error) => {
+    assert.equal(error, failure);
+    return true;
+  });
+  assert.deepEqual(received, ["/api/listAgents"]);
+  assert.deepEqual(Object.getOwnPropertyDescriptors(failure), original);
+});
+
 test("sendPrompt marks transport loss unknown with a no-retry hint", async (t) => {
   t.mock.method(globalThis, "fetch", async (url) => {
     if (String(url).endsWith("/api/listAgents")) return new Response(JSON.stringify(roster), { status: 200 });
@@ -85,6 +117,29 @@ test("sendPrompt marks transport loss unknown with a no-retry hint", async (t) =
   });
 });
 
+test("sendPrompt preserves an unknown timeout without mutating its DOMException", async (t) => {
+  const failure = new DOMException("The operation was aborted due to timeout", "TimeoutError");
+  const original = Object.getOwnPropertyDescriptors(failure);
+  const received = [];
+  t.mock.method(globalThis, "fetch", async (url) => {
+    received.push(new URL(url).pathname);
+    if (String(url).endsWith("/api/listAgents")) return new Response(JSON.stringify(roster), { status: 200 });
+    throw failure;
+  });
+
+  await assert.rejects(sendPrompt(session, "General", "hi"), (error) => {
+    assert.equal(error.delivery, "unknown");
+    assert.equal(error.targetId, "bot-1");
+    assert.equal(error.name, "TimeoutError");
+    assert.equal(error.cause, failure);
+    assert.match(error.message, /delivery unknown; check the thread before resending/);
+    return true;
+  });
+  assert.deepEqual(received, ["/api/listAgents", "/api/sendPrompt"]);
+  assert.equal(failure.message, "The operation was aborted due to timeout");
+  assert.deepEqual(Object.getOwnPropertyDescriptors(failure), original);
+});
+
 test("oversized gateway responses abort mid-stream instead of buffering", async (t) => {
   mockGateway(t, () => new Response("x".repeat(GATEWAY_MAX_RESPONSE_BYTES + 8), { status: 200 }));
   await assert.rejects(sendPrompt(session, "General", "hi"), /too large/);