diff --git a/extensions/telegram/src/bot/delivery.test.ts b/extensions/telegram/src/bot/delivery.test.ts
index 086b1c46a78f..716aa8d0cf29 100644
--- a/extensions/telegram/src/bot/delivery.test.ts
+++ b/extensions/telegram/src/bot/delivery.test.ts
@@ -218,9 +218,10 @@ function createHtmlParseError(operation = "sendMessage") {
   );
 }
 
-function createWrappedPreConnectHttpError(operation = "sendMessage") {
-  const root = Object.assign(new Error("getaddrinfo ENOTFOUND api.telegram.org"), {
-    code: "ENOTFOUND",
+function createWrappedConnectTimeoutHttpError(operation = "sendMessage") {
+  const root = Object.assign(new Error("Connect Timeout Error"), {
+    name: "ConnectTimeoutError",
+    code: "UND_ERR_CONNECT_TIMEOUT",
   });
   const fetchError = Object.assign(new TypeError("fetch failed"), { cause: root });
   return Object.assign(new Error(`Network request for '${operation}' failed!`), {
@@ -1027,12 +1028,12 @@ describe("deliverReplies", () => {
     expect(runtime.error).toHaveBeenCalledTimes(1);
   });
 
-  it("retries final text sends for wrapped pre-connect grammY HttpError envelopes", async () => {
+  it("retries final text sends for wrapped Undici connect timeouts", async () => {
     vi.useFakeTimers();
     const runtime = createRuntime();
     const sendMessage = vi
       .fn()
-      .mockRejectedValueOnce(createWrappedPreConnectHttpError("sendMessage"))
+      .mockRejectedValueOnce(createWrappedConnectTimeoutHttpError("sendMessage"))
       .mockResolvedValueOnce({
         message_id: 12,
         chat: { id: "123" },
diff --git a/extensions/telegram/src/network-errors.test.ts b/extensions/telegram/src/network-errors.test.ts
index 8381b081952d..7e3ce9bc5aa7 100644
--- a/extensions/telegram/src/network-errors.test.ts
+++ b/extensions/telegram/src/network-errors.test.ts
@@ -239,7 +239,7 @@ describe("isSafeToRetrySendError", () => {
     ["ECONNRESET", "read ECONNRESET", false],
     ["ETIMEDOUT", "connect ETIMEDOUT", false],
     ["EPIPE", "write EPIPE", false],
-    ["UND_ERR_CONNECT_TIMEOUT", "connect timeout", false],
+    ["UND_ERR_CONNECT_TIMEOUT", "connect timeout", true],
   ])("returns %s => %s", (code, message, expected) => {
     expect(isSafeToRetrySendError(errorWithCode(message, code))).toBe(expected);
   });
diff --git a/extensions/telegram/src/network-errors.ts b/extensions/telegram/src/network-errors.ts
index dbcfb08329ea..1c299fc1cf59 100644
--- a/extensions/telegram/src/network-errors.ts
+++ b/extensions/telegram/src/network-errors.ts
@@ -47,6 +47,7 @@ const PRE_CONNECT_ERROR_CODES = new Set([
   "ENETDOWN", // Local network interface is down before connect completes (never sent)
   "ENETUNREACH", // No route to host (never sent)
   "EHOSTUNREACH", // Host unreachable (never sent)
+  "UND_ERR_CONNECT_TIMEOUT", // TCP/TLS connect timeout (request never sent)
 ]);
 
 const RECOVERABLE_ERROR_NAMES = new Set([
diff --git a/extensions/telegram/src/send.test.ts b/extensions/telegram/src/send.test.ts
index 7bb87c46edfb..4a60ba7876b9 100644
--- a/extensions/telegram/src/send.test.ts
+++ b/extensions/telegram/src/send.test.ts
@@ -2401,11 +2401,12 @@ describe("sendMessageTelegram", () => {
     vi.useRealTimers();
   });
 
-  it("retries wrapped pre-connect HttpError sends", async () => {
+  it("retries wrapped Undici connect timeout sends", async () => {
     vi.useFakeTimers();
     const chatId = "123";
-    const root = Object.assign(new Error("connect ECONNREFUSED api.telegram.org"), {
-      code: "ECONNREFUSED",
+    const root = Object.assign(new Error("Connect Timeout Error"), {
+      name: "ConnectTimeoutError",
+      code: "UND_ERR_CONNECT_TIMEOUT",
     });
     const fetchError = Object.assign(new TypeError("fetch failed"), { cause: root });
     const err = Object.assign(new Error("Network request for 'sendMessage' failed!"), {