diff --git a/src/telegram/network-errors.test.ts b/src/telegram/network-errors.test.ts
index b92081a8284..c7206305b04 100644
--- a/src/telegram/network-errors.test.ts
+++ b/src/telegram/network-errors.test.ts
@@ -40,7 +40,7 @@ describe("isRecoverableTelegramNetworkError", () => {
   });
 
   it("skips broad message matches for send context", () => {
-    const networkRequestErr = new Error("Network request for 'sendMessage' failed!");
+    const networkRequestErr = new Error("Network request for 'sendMessage' timed out!");
     expect(isRecoverableTelegramNetworkError(networkRequestErr, { context: "send" })).toBe(false);
     expect(isRecoverableTelegramNetworkError(networkRequestErr, { context: "polling" })).toBe(true);
 
@@ -49,6 +49,20 @@ describe("isRecoverableTelegramNetworkError", () => {
     expect(isRecoverableTelegramNetworkError(undiciSnippetErr, { context: "polling" })).toBe(true);
   });
 
+  it("treats grammY network envelope errors as recoverable in send context", () => {
+    expect(
+      isRecoverableTelegramNetworkError(new Error("Network request for 'sendMessage' failed!"), {
+        context: "send",
+      }),
+    ).toBe(true);
+    expect(
+      isRecoverableTelegramNetworkError(
+        new Error("Network request for 'sendMessage' failed after 2 attempts."),
+        { context: "send" },
+      ),
+    ).toBe(true);
+  });
+
   it("returns false for unrelated errors", () => {
     expect(isRecoverableTelegramNetworkError(new Error("invalid token"))).toBe(false);
   });
diff --git a/src/telegram/network-errors.ts b/src/telegram/network-errors.ts
index f9b7061dd61..7413a20e9d2 100644
--- a/src/telegram/network-errors.ts
+++ b/src/telegram/network-errors.ts
@@ -33,6 +33,8 @@ const RECOVERABLE_ERROR_NAMES = new Set([
 ]);
 
 const ALWAYS_RECOVERABLE_MESSAGES = new Set(["fetch failed", "typeerror: fetch failed"]);
+const GRAMMY_NETWORK_REQUEST_FAILED_RE =
+  /^network request(?:\s+for\s+["']?[^"']+["']?)?\s+failed(?:\s+after\b.*)?[!.]?$/i;
 
 const RECOVERABLE_MESSAGE_SNIPPETS = [
   "undici",
@@ -106,6 +108,9 @@ export function isRecoverableTelegramNetworkError(
     if (message && ALWAYS_RECOVERABLE_MESSAGES.has(message)) {
       return true;
     }
+    if (message && GRAMMY_NETWORK_REQUEST_FAILED_RE.test(message)) {
+      return true;
+    }
     if (allowMessageMatch && message) {
       if (RECOVERABLE_MESSAGE_SNIPPETS.some((snippet) => message.includes(snippet))) {
         return true;
diff --git a/src/telegram/send.test.ts b/src/telegram/send.test.ts
index 59c98ea3a96..8f73753c70d 100644
--- a/src/telegram/send.test.ts
+++ b/src/telegram/send.test.ts
@@ -779,6 +779,29 @@ describe("sendMessageTelegram", () => {
     expect(sendMessage).toHaveBeenCalledTimes(1);
   });
 
+  it("retries when grammY network envelope message includes failed-after wording", async () => {
+    const chatId = "123";
+    const sendMessage = vi
+      .fn()
+      .mockRejectedValueOnce(new Error("Network request for 'sendMessage' failed after 1 attempts."))
+      .mockResolvedValueOnce({
+        message_id: 7,
+        chat: { id: chatId },
+      });
+    const api = { sendMessage } as unknown as {
+      sendMessage: typeof sendMessage;
+    };
+
+    const result = await sendMessageTelegram(chatId, "hi", {
+      token: "tok",
+      api,
+      retry: { attempts: 2, minDelayMs: 0, maxDelayMs: 0, jitter: 0 },
+    });
+
+    expect(sendMessage).toHaveBeenCalledTimes(2);
+    expect(result).toEqual({ messageId: "7", chatId });
+  });
+
   it("sends GIF media as animation", async () => {
     const chatId = "123";
     const sendAnimation = vi.fn().mockResolvedValue({