diff --git a/extensions/telegram/src/bot.fetch-abort.test.ts b/extensions/telegram/src/bot.fetch-abort.test.ts
index 6b9b9934266a..6110ba64cf3e 100644
--- a/extensions/telegram/src/bot.fetch-abort.test.ts
+++ b/extensions/telegram/src/bot.fetch-abort.test.ts
@@ -1,7 +1,7 @@
 // Telegram tests cover bot.fetch abort plugin behavior.
 import { toErrorObject as toLintErrorObject } from "openclaw/plugin-sdk/error-runtime";
 import { describe, expect, it, vi } from "vitest";
-import { isTelegramPollingNetworkError } from "./network-errors.js";
+import { isTelegramPollingNetworkError, TelegramRequestNotStartedError } from "./network-errors.js";
 
 const { botCtorSpy, telegramBotDepsForTest } =
   await import("./bot.create-telegram-bot.test-harness.js");
@@ -357,6 +357,36 @@ describe("createTelegramBot fetch abort", () => {
     expect(cancelMisdirectedBody).toHaveBeenCalledOnce();
   });
 
+  it.each([
+    ["without fallback", false],
+    ["after one fallback", true],
+  ])(
+    "rejects a terminal actual 421 %s and cancels every response body",
+    async (_name, fallback) => {
+      const cancelBodies = Array.from({ length: fallback ? 2 : 1 }, () => vi.fn());
+      const fetchSpy = vi.fn();
+      for (const cancel of cancelBodies) {
+        fetchSpy.mockResolvedValueOnce(
+          new Response(new ReadableStream<Uint8Array>({ cancel }), { status: 421 }),
+        );
+      }
+      const forceFallback = fallback ? vi.fn(() => true) : undefined;
+      const { clientFetch } = createWrappedTelegramClientFetchWithTransport({
+        fetch: fetchSpy as typeof fetch,
+        ...(forceFallback ? { forceFallback } : {}),
+      });
+
+      await expect(
+        clientFetch("https://api.telegram.org/bot123456:ABC/sendMessage"),
+      ).rejects.toBeInstanceOf(TelegramRequestNotStartedError);
+
+      expect(fetchSpy).toHaveBeenCalledTimes(cancelBodies.length);
+      for (const cancel of cancelBodies) {
+        expect(cancel).toHaveBeenCalledOnce();
+      }
+    },
+  );
+
   it("retries Telegram 421 fetch errors after forcing transport fallback", async () => {
     const forceFallback = vi.fn(() => true);
     const fetchSpy = vi
@@ -376,6 +406,22 @@ describe("createTelegramBot fetch abort", () => {
     expect(fetchSpy).toHaveBeenCalledTimes(2);
   });
 
+  it("keeps a thrown 421-shaped edge error distinct from request-not-started custody", async () => {
+    const edgeError = Object.assign(new Error("421 Misdirected Request"), { status: 421 });
+    const forceFallback = vi.fn(() => false);
+    const fetchSpy = vi.fn().mockRejectedValue(edgeError);
+    const { clientFetch } = createWrappedTelegramClientFetchWithTransport({
+      fetch: fetchSpy as typeof fetch,
+      forceFallback,
+    });
+
+    await expect(clientFetch("https://api.telegram.org/bot123456:ABC/sendMessage")).rejects.toBe(
+      edgeError,
+    );
+    expect(edgeError).not.toBeInstanceOf(TelegramRequestNotStartedError);
+    expect(forceFallback).toHaveBeenCalledWith("misdirected-request");
+  });
+
   it("preserves the original fetch error when tagging cannot attach metadata", async () => {
     const frozenError = Object.freeze(
       Object.assign(new TypeError("fetch failed"), {
diff --git a/extensions/telegram/src/bot/delivery.send.ts b/extensions/telegram/src/bot/delivery.send.ts
index e60a64acc3e3..953b348ef0d3 100644
--- a/extensions/telegram/src/bot/delivery.send.ts
+++ b/extensions/telegram/src/bot/delivery.send.ts
@@ -4,7 +4,7 @@ import type { MarkdownTableMode } from "openclaw/plugin-sdk/config-contracts";
 import { createChannelApiRetryRunner } from "openclaw/plugin-sdk/retry-runtime";
 import type { RuntimeEnv } from "openclaw/plugin-sdk/runtime-env";
 import { withTelegramApiErrorLogging } from "../api-logging.js";
-import { isSafeToRetrySendError, isTelegramRateLimitError } from "../network-errors.js";
+import { rethrowTelegramSendError, shouldRetryTelegramSendError } from "../network-errors.js";
 import {
   buildTelegramSendParams,
   getTelegramNativeQuoteReplyMessageId,
@@ -32,7 +32,7 @@ export { buildTelegramSendParams } from "../reply-parameters.js";
 
 function createTelegramDeliverySendRetry() {
   return createChannelApiRetryRunner({
-    shouldRetry: (err) => isSafeToRetrySendError(err) || isTelegramRateLimitError(err),
+    shouldRetry: shouldRetryTelegramSendError,
     strictShouldRetry: true,
     retryAfterMaxDelayMs: TELEGRAM_OUTBOUND_RETRY_AFTER_CAP_MS,
   });
@@ -61,7 +61,7 @@ export async function sendTelegramWithThreadFallback<T>(params: {
             getTelegramNativeQuoteReplyMessageId(requestParams) && isTelegramQuoteParamError(error)
           ),
         fn: () => requestWithRetry(() => params.send(requestParams), operation),
-      }),
+      }).catch(rethrowTelegramSendError),
   });
   return result;
 }
diff --git a/extensions/telegram/src/bot/delivery.test.ts b/extensions/telegram/src/bot/delivery.test.ts
index f2cafd2c0a8c..5a06b77b6995 100644
--- a/extensions/telegram/src/bot/delivery.test.ts
+++ b/extensions/telegram/src/bot/delivery.test.ts
@@ -67,6 +67,7 @@ vi.mock("../sent-message-cache.js", async (importOriginal) => {
 vi.resetModules();
 const { deliverReplies } = await import("./delivery.js");
 const { sendTelegramText } = await import("./delivery.send.js");
+const { PlatformMessageNotDispatchedError } = await import("openclaw/plugin-sdk/error-runtime");
 
 vi.mock("grammy", () => ({
   API_CONSTANTS: {
@@ -84,6 +85,8 @@ vi.mock("grammy", () => ({
   },
 }));
 
+const { TelegramRequestNotStartedError } = await import("../network-errors.js");
+
 function createRuntime(withLog = true): RuntimeStub {
   return {
     error: vi.fn(),
@@ -285,10 +288,13 @@ function createWrappedConnectTimeoutHttpError(operation = "sendMessage") {
   });
 }
 
-function createPlainHttpError(operation = "sendMessage") {
+function createPlainHttpError(
+  operation = "sendMessage",
+  error: unknown = new TypeError("fetch failed"),
+) {
   return Object.assign(new Error(`Network request for '${operation}' failed!`), {
     name: "HttpError",
-    error: new TypeError("fetch failed"),
+    error,
   });
 }
 
@@ -1651,6 +1657,33 @@ describe("deliverReplies", () => {
     expect(runtime.error).toHaveBeenCalledTimes(1);
   });
 
+  it("maps an exhausted request-not-started marker to streaming no-dispatch custody", async () => {
+    const runtime = createRuntime();
+    const terminal = createPlainHttpError("sendMessage", new TelegramRequestNotStartedError());
+    const sendMessage = vi.fn().mockRejectedValue(terminal);
+
+    let observed: unknown;
+    try {
+      await sendTelegramText(createBot({ sendMessage }), "123", "hello", runtime);
+    } catch (error) {
+      observed = error;
+    }
+
+    expect(observed).toBeInstanceOf(PlatformMessageNotDispatchedError);
+    expect(observed).toHaveProperty("cause", terminal);
+    expect(sendMessage).toHaveBeenCalledTimes(3);
+  });
+
+  it("keeps broad 421-shaped streaming send errors ambiguous", async () => {
+    const edgeError = Object.assign(new Error("421 Misdirected Request"), { status: 421 });
+    const sendMessage = vi.fn().mockRejectedValue(edgeError);
+
+    await expect(
+      sendTelegramText(createBot({ sendMessage }), "123", "hello", createRuntime()),
+    ).rejects.toBe(edgeError);
+    expect(sendMessage).toHaveBeenCalledOnce();
+  });
+
   it("does not retry DM topic media sends without the topic id", async () => {
     const runtime = createRuntime();
     const sendPhoto = vi.fn().mockRejectedValueOnce(createThreadNotFoundError("sendPhoto"));
diff --git a/extensions/telegram/src/chunk-delivery.test.ts b/extensions/telegram/src/chunk-delivery.test.ts
index 297a98c9c594..1d9fb7ef0557 100644
--- a/extensions/telegram/src/chunk-delivery.test.ts
+++ b/extensions/telegram/src/chunk-delivery.test.ts
@@ -1,4 +1,5 @@
 import { isChannelPartialDeliveryError } from "openclaw/plugin-sdk/channel-inbound";
+import { PlatformMessageNotDispatchedError } from "openclaw/plugin-sdk/error-runtime";
 import { describe, expect, it, vi } from "vitest";
 import { createTelegramChunkDeliveryTracker } from "./chunk-delivery.js";
 
@@ -9,6 +10,19 @@ describe("Telegram chunk delivery", () => {
   it.each([
     [telegramError(400, "content rejected"), true],
     [Object.assign(new Error("dns failed"), { code: "ENOTFOUND" }), true],
+    [
+      new PlatformMessageNotDispatchedError("request not started", {
+        cause: new Error("transport unavailable"),
+      }),
+      true,
+    ],
+    [
+      new PlatformMessageNotDispatchedError("payload rejected", {
+        cause: new Error("invalid payload"),
+        retryable: false,
+      }),
+      false,
+    ],
     [telegramError(400, "message thread not found"), false],
     [telegramError(401, "unauthorized"), false],
     [telegramError(429, "rate limited"), false],
diff --git a/extensions/telegram/src/client-fetch.ts b/extensions/telegram/src/client-fetch.ts
index 537bd8079251..f017f5ac08a2 100644
--- a/extensions/telegram/src/client-fetch.ts
+++ b/extensions/telegram/src/client-fetch.ts
@@ -3,7 +3,11 @@ import type { ApiClientOptions } from "grammy";
 import { responseWithRelease } from "openclaw/plugin-sdk/fetch-runtime";
 import { normalizeOptionalLowercaseString } from "openclaw/plugin-sdk/string-coerce-runtime";
 import type { TelegramTransport } from "./fetch.js";
-import { isTelegramMisdirectedRequestError, tagTelegramNetworkError } from "./network-errors.js";
+import {
+  isTelegramMisdirectedRequestError,
+  tagTelegramNetworkError,
+  TelegramRequestNotStartedError,
+} from "./network-errors.js";
 import { resolveTelegramRequestTimeoutMs } from "./request-timeouts.js";
 
 type TelegramFetchInput = Parameters<NonNullable<ApiClientOptions["fetch"]>>[0];
@@ -142,7 +146,7 @@ export function createTelegramClientFetch(params: {
       !requestSignal?.aborted &&
       params.transport?.forceFallback?.(reason) === true;
 
-    const runFetch = async () => {
+    const runFetch = async (allowMisdirectedFallback = false): Promise<Response> => {
       const controller = new AbortController();
       const abortWith = (signal: Pick<TelegramAbortSignalLike, "reason">) =>
         controller.abort(signal.reason);
@@ -195,6 +199,18 @@ export function createTelegramClientFetch(params: {
           ...init,
           signal: controller.signal,
         });
+        if (response.status === 421) {
+          const retry =
+            allowMisdirectedFallback && canForceTransportFallback("misdirected-request");
+          // HTTP 421 permits retrying a non-idempotent request;
+          // arbitrary thrown 421 shapes do not own that fact.
+          await response.body?.cancel().catch(() => undefined);
+          if (retry) {
+            await releaseRequest();
+            return runFetch();
+          }
+          throw new TelegramRequestNotStartedError();
+        }
         // grammY consumes JSON after fetch resolves; keep its deadline and
         // cancellation linked until the response body settles.
         return responseWithRelease(response, releaseRequest);
@@ -208,12 +224,7 @@ export function createTelegramClientFetch(params: {
     };
 
     try {
-      const response = await runFetch();
-      if (response.status === 421 && canForceTransportFallback("misdirected-request")) {
-        await response.body?.cancel().catch(() => undefined);
-        return await runFetch();
-      }
-      return response;
+      return await runFetch(true);
     } catch (err) {
       if (
         requestTimeoutMs &&
diff --git a/extensions/telegram/src/fetch.test.ts b/extensions/telegram/src/fetch.test.ts
index 1c72565a8e6e..ad8edbeceaf3 100644
--- a/extensions/telegram/src/fetch.test.ts
+++ b/extensions/telegram/src/fetch.test.ts
@@ -6,6 +6,7 @@ import { expectDefined } from "@openclaw/normalization-core";
 import { resolveFetch } from "openclaw/plugin-sdk/fetch-runtime";
 import { MAX_DATE_TIMESTAMP_MS } from "openclaw/plugin-sdk/number-runtime";
 import { afterEach, beforeAll, beforeEach, describe, expect, it, vi } from "vitest";
+import { isSafeToRetrySendError, TelegramRequestNotStartedError } from "./network-errors.js";
 
 const setDefaultResultOrder = vi.hoisted(() => vi.fn());
 const getDefaultResultOrder = vi.hoisted(() => vi.fn(() => "ipv4first"));
@@ -1053,12 +1054,7 @@ describe("resolveTelegramFetch", () => {
   });
 
   it("cools down a repeatedly failing sticky fallback and probes earlier attempts", async () => {
-    for (let i = 0; i < 7; i += 1) {
-      undiciFetch.mockRejectedValueOnce(buildFetchFallbackError("ENETUNREACH"));
-    }
-    undiciFetch
-      .mockRejectedValueOnce(buildFetchFallbackError("ENETUNREACH"))
-      .mockRejectedValueOnce(buildFetchFallbackError("ENETUNREACH"));
+    undiciFetch.mockRejectedValue(buildFetchFallbackError("ENETUNREACH"));
 
     const resolved = resolveTelegramFetchOrThrow(undefined, {
       network: {
@@ -1075,10 +1071,15 @@ describe("resolveTelegramFetch", () => {
         "fetch failed",
       );
     }
-    await expect(resolved("https://api.telegram.org/botx/getUpdates")).rejects.toThrow(
-      "temporarily unhealthy",
-    );
+    let terminalError: unknown;
+    try {
+      await resolved("https://api.telegram.org/botx/getUpdates");
+    } catch (error) {
+      terminalError = error;
+    }
 
+    expect(terminalError).toBeInstanceOf(TelegramRequestNotStartedError);
+    expect(isSafeToRetrySendError(terminalError)).toBe(true);
     expect(undiciFetch).toHaveBeenCalledTimes(9);
     expect(getDispatcherFromUndiciCall(7)).toBe(getDispatcherFromUndiciCall(3));
     expect(getDispatcherFromUndiciCall(8)).toBe(getDispatcherFromUndiciCall(1));
diff --git a/extensions/telegram/src/fetch.ts b/extensions/telegram/src/fetch.ts
index d8a496f1344f..07c5c7d01f4d 100644
--- a/extensions/telegram/src/fetch.ts
+++ b/extensions/telegram/src/fetch.ts
@@ -32,6 +32,7 @@ import {
   resolveTelegramDnsResultOrderDecision,
   TELEGRAM_DNS_RESULT_ORDER_ENV,
 } from "./network-config.js";
+import { TelegramRequestNotStartedError } from "./network-errors.js";
 import { getProxyUrlFromFetch, makeProxyFetch } from "./proxy.js";
 
 const log = createSubsystemLogger("telegram/network");
@@ -423,18 +424,7 @@ function formatErrorCodes(err: unknown): string {
   return codes.length > 0 ? codes.join(",") : "none";
 }
 
-class TelegramTransportAttemptUnhealthyError extends Error {
-  constructor(unhealthyUntilMs: number) {
-    const remainingMs = Math.max(0, unhealthyUntilMs - Date.now());
-    super(`telegram transport attempt temporarily unhealthy; retry after ${remainingMs}ms`);
-    this.name = "TelegramTransportAttemptUnhealthyError";
-  }
-}
-
 function shouldUseTelegramTransportFallback(err: unknown): boolean {
-  if (err instanceof TelegramTransportAttemptUnhealthyError) {
-    return true;
-  }
   const ctx: TelegramTransportFallbackContext = {
     message:
       err && typeof err === "object" && "message" in err
@@ -651,7 +641,10 @@ export function resolveTelegramTransport(
     if (!isFutureDateTimestampMs(health.unhealthyUntilMs)) {
       return null;
     }
-    return new TelegramTransportAttemptUnhealthyError(health.unhealthyUntilMs);
+    const remainingMs = Math.max(0, health.unhealthyUntilMs - Date.now());
+    return new TelegramRequestNotStartedError(
+      `Telegram transport attempts are cooling down; retry after ${remainingMs}ms`,
+    );
   };
 
   const recordAttemptFailure = (attemptIndex: number, err: unknown): void => {
diff --git a/extensions/telegram/src/network-errors.test.ts b/extensions/telegram/src/network-errors.test.ts
index 80b772ebd6a8..956859ff32e1 100644
--- a/extensions/telegram/src/network-errors.test.ts
+++ b/extensions/telegram/src/network-errors.test.ts
@@ -10,6 +10,7 @@ import {
   isTelegramPollingNetworkError,
   isTelegramServerError,
   tagTelegramNetworkError,
+  TelegramRequestNotStartedError,
 } from "./network-errors.js";
 
 const errorWithCode = (message: string, code: string) =>
@@ -171,6 +172,17 @@ describe("isRecoverableTelegramNetworkError", () => {
     ).toBe(true);
   });
 
+  it("keeps request-not-started markers recoverable across Telegram contexts", () => {
+    const marker = new TelegramRequestNotStartedError();
+    const wrapped = Object.assign(new Error("Network request for 'getUpdates' failed!"), {
+      name: "HttpError",
+      error: marker,
+    });
+
+    expect(isRecoverableTelegramNetworkError(marker, { context: "send" })).toBe(true);
+    expect(isRecoverableTelegramNetworkError(wrapped, { context: "polling" })).toBe(true);
+  });
+
   it("returns false for unrelated errors", () => {
     expect(isRecoverableTelegramNetworkError(new Error("invalid token"))).toBe(false);
   });
@@ -279,6 +291,17 @@ describe("isSafeToRetrySendError", () => {
     expect(isSafeToRetrySendError(wrapped)).toBe(false);
   });
 
+  it("accepts only direct and exact grammY-wrapped request-not-started markers", () => {
+    const marker = new TelegramRequestNotStartedError();
+
+    expect(isSafeToRetrySendError(marker)).toBe(true);
+    expect(
+      isSafeToRetrySendError(
+        new MockHttpError("Network request for 'sendMessage' failed!", marker),
+      ),
+    ).toBe(true);
+  });
+
   it.each([
     ["status", Object.assign(new Error("Misdirected Request"), { status: 421 })],
     ["statusCode", Object.assign(new Error("Misdirected Request"), { statusCode: "421" })],
@@ -297,8 +320,8 @@ describe("isSafeToRetrySendError", () => {
         Object.assign(new Error("Misdirected Request"), { status: 421 }),
       ),
     ],
-  ])("treats Telegram 421 Misdirected Request as safe to retry via %s", (_name, err) => {
-    expect(isSafeToRetrySendError(err)).toBe(true);
+  ])("does not infer safe retry from broad Telegram 421 shape %s", (_name, err) => {
+    expect(isSafeToRetrySendError(err)).toBe(false);
   });
 
   it("does not parse malformed status strings as Telegram 421", () => {
diff --git a/extensions/telegram/src/network-errors.ts b/extensions/telegram/src/network-errors.ts
index 580c15f0c7ea..44f3db3bbc5c 100644
--- a/extensions/telegram/src/network-errors.ts
+++ b/extensions/telegram/src/network-errors.ts
@@ -3,6 +3,7 @@ import {
   collectErrorGraphCandidates,
   extractErrorCode,
   formatErrorMessage,
+  PlatformMessageNotDispatchedError,
   readErrorName,
 } from "openclaw/plugin-sdk/error-runtime";
 import { parseStrictNonNegativeInteger } from "openclaw/plugin-sdk/number-runtime";
@@ -11,6 +12,27 @@ import { normalizeLowercaseStringOrEmpty } from "openclaw/plugin-sdk/string-coer
 
 const TELEGRAM_NETWORK_ORIGIN = Symbol("openclaw.telegram.network-origin");
 
+export class TelegramRequestNotStartedError extends Error {
+  constructor(message = "Telegram request did not start") {
+    super(message);
+    this.name = "TelegramRequestNotStartedError";
+  }
+}
+
+function isTelegramRequestNotStartedError(err: unknown): boolean {
+  return (
+    err instanceof TelegramRequestNotStartedError ||
+    (readErrorName(err) === "HttpError" &&
+      (err as { error?: unknown }).error instanceof TelegramRequestNotStartedError)
+  );
+}
+
+export function rethrowTelegramSendError(err: unknown): never {
+  throw isTelegramRequestNotStartedError(err)
+    ? new PlatformMessageNotDispatchedError("Telegram request not started", { cause: err })
+    : err;
+}
+
 const TELEGRAM_ADDITIONAL_TRANSIENT_ERROR_CODES = new Set([
   "ENETDOWN",
   "ESOCKETTIMEDOUT",
@@ -20,16 +42,9 @@ const TELEGRAM_ADDITIONAL_TRANSIENT_ERROR_CODES = new Set([
   "ERR_NETWORK",
 ]);
 
-/**
- * Error codes that are safe to retry for non-idempotent send operations (e.g. sendMessage).
- *
- * These represent failures that occur *before* the request reaches Telegram's servers,
- * meaning the message was definitely not delivered and it is safe to retry.
- *
- * Contrast with the full transient set, which includes codes like ECONNRESET and ETIMEDOUT
- * that can fire *after* Telegram has already received and delivered a message — retrying
- * those would cause duplicate messages.
- */
+// These exact local codes fail before request publication and are safe for
+// non-idempotent sends. Resets and timeouts can occur after delivery, so
+// retrying them could duplicate a visible message.
 const TELEGRAM_ADDITIONAL_PRE_CONNECT_ERROR_CODES = new Set([
   "ENETDOWN", // Local network interface is down before connect completes (never sent)
   "EHOSTUNREACH", // Host unreachable (never sent)
@@ -194,19 +209,15 @@ export function isTelegramPollingNetworkError(err: unknown): boolean {
   return getTelegramNetworkErrorOrigin(err)?.method === "getupdates";
 }
 
-/**
- * Returns true if the error is safe to retry for a non-idempotent Telegram send operation
- * (e.g. sendMessage). Only matches errors that are guaranteed to have occurred *before*
- * the request reached Telegram's servers, preventing duplicate message delivery.
- *
- * Use this instead of isRecoverableTelegramNetworkError for sendMessage/sendPhoto/etc.
- * calls where a retry would create a duplicate visible message.
- */
+/** True only for channel-owned no-send proof or proven pre-connect failures. */
 export function isSafeToRetrySendError(err: unknown): boolean {
   if (!err) {
     return false;
   }
-  if (isTelegramMisdirectedRequestError(err)) {
+  if (err instanceof PlatformMessageNotDispatchedError) {
+    return err.retryable;
+  }
+  if (isTelegramRequestNotStartedError(err)) {
     return true;
   }
   for (const candidate of collectTelegramErrorCandidates(err)) {
@@ -217,6 +228,10 @@ export function isSafeToRetrySendError(err: unknown): boolean {
   return false;
 }
 
+export function shouldRetryTelegramSendError(err: unknown): boolean {
+  return isSafeToRetrySendError(err) || isTelegramRateLimitError(err);
+}
+
 function hasTelegramErrorCode(err: unknown, matches: (code: number) => boolean): boolean {
   for (const candidate of collectTelegramErrorCandidates(err)) {
     if (!candidate || typeof candidate !== "object" || !("error_code" in candidate)) {
@@ -316,6 +331,9 @@ export function isRecoverableTelegramNetworkError(
   if (!err) {
     return false;
   }
+  if (isTelegramRequestNotStartedError(err)) {
+    return true;
+  }
   const allowMessageMatch =
     typeof options.allowMessageMatch === "boolean"
       ? options.allowMessageMatch
diff --git a/extensions/telegram/src/send-context.ts b/extensions/telegram/src/send-context.ts
index 1b73a95ffc45..6f76669776b3 100644
--- a/extensions/telegram/src/send-context.ts
+++ b/extensions/telegram/src/send-context.ts
@@ -13,7 +13,7 @@ import { withTelegramApiErrorLogging } from "./api-logging.js";
 import { normalizeTelegramApiRoot } from "./api-root.js";
 import { asTelegramClientFetch, createTelegramClientFetch } from "./client-fetch.js";
 import { resolveTelegramTransport, type TelegramTransport } from "./fetch.js";
-import { isSafeToRetrySendError, isTelegramRateLimitError } from "./network-errors.js";
+import { rethrowTelegramSendError, shouldRetryTelegramSendError } from "./network-errors.js";
 import type { TelegramOutboundPromptContextMessage as TelegramMessageLike } from "./outbound-message-context.js";
 import { makeProxyFetch } from "./proxy.js";
 import {
@@ -571,14 +571,15 @@ export function createTelegramNonIdempotentRequestWithDiag(params: {
   verbose?: boolean;
   useApiErrorLogging?: boolean;
 }): TelegramRequestWithDiag {
-  return createTelegramRequestWithDiag({
+  const request = createTelegramRequestWithDiag({
     cfg: params.cfg,
     account: params.account,
     retry: params.retry,
     verbose: params.verbose,
     useApiErrorLogging: params.useApiErrorLogging,
     retryAfterMaxDelayMs: TELEGRAM_OUTBOUND_RETRY_AFTER_CAP_MS,
-    shouldRetry: (err) => isSafeToRetrySendError(err) || isTelegramRateLimitError(err),
+    shouldRetry: shouldRetryTelegramSendError,
     strictShouldRetry: true,
   });
+  return (fn, label, options) => request(fn, label, options).catch(rethrowTelegramSendError);
 }
diff --git a/extensions/telegram/src/send.test.ts b/extensions/telegram/src/send.test.ts
index cfc76944a6e7..e91c61fdfb50 100644
--- a/extensions/telegram/src/send.test.ts
+++ b/extensions/telegram/src/send.test.ts
@@ -69,6 +69,8 @@ const {
   probeVideoDimensions,
 } = getTelegramSendTestMocks();
 const telegramSendModule = await importTelegramSendModule();
+const { PlatformMessageNotDispatchedError } = await import("openclaw/plugin-sdk/error-runtime");
+const { TelegramRequestNotStartedError } = await import("./network-errors.js");
 const { getChildLogger, resetLogger, setLoggerOverride } =
   await import("openclaw/plugin-sdk/runtime-env");
 const {
@@ -3419,6 +3421,49 @@ describe("sendMessageTelegram", () => {
     vi.useRealTimers();
   });
 
+  it("maps an exhausted request-not-started marker to durable no-dispatch custody", async () => {
+    const chatId = "123";
+    const terminal = Object.assign(new Error("Network request for 'sendMessage' failed!"), {
+      name: "HttpError",
+      error: new TelegramRequestNotStartedError(),
+    });
+    const sendMessage = vi.fn().mockRejectedValue(terminal);
+    const api = { sendMessage } as unknown as { sendMessage: typeof sendMessage };
+
+    let observed: unknown;
+    try {
+      await sendMessageTelegram(chatId, "hi", {
+        cfg: TELEGRAM_TEST_CFG,
+        token: "tok",
+        api,
+        retry: { attempts: 2, minDelayMs: 0, maxDelayMs: 0, jitter: 0 },
+      });
+    } catch (error) {
+      observed = error;
+    }
+
+    expect(observed).toBeInstanceOf(PlatformMessageNotDispatchedError);
+    expect(observed).toHaveProperty("cause", terminal);
+    expect(sendMessage).toHaveBeenCalledTimes(2);
+  });
+
+  it("keeps broad 421-shaped durable send errors ambiguous", async () => {
+    const chatId = "123";
+    const edgeError = Object.assign(new Error("421 Misdirected Request"), { status: 421 });
+    const sendMessage = vi.fn().mockRejectedValue(edgeError);
+    const api = { sendMessage } as unknown as { sendMessage: typeof sendMessage };
+
+    await expect(
+      sendMessageTelegram(chatId, "hi", {
+        cfg: TELEGRAM_TEST_CFG,
+        token: "tok",
+        api,
+        retry: { attempts: 2, minDelayMs: 0, maxDelayMs: 0, jitter: 0 },
+      }),
+    ).rejects.toBe(edgeError);
+    expect(sendMessage).toHaveBeenCalledOnce();
+  });
+
   it("does not retry on non-transient errors", async () => {
     const chatId = "123";
     const sendMessage = vi.fn().mockRejectedValue(new Error("400: Bad Request"));