diff --git a/extensions/telegram/src/bot-message-dispatch.ts b/extensions/telegram/src/bot-message-dispatch.ts
index a9c0e625508..26a2925470f 100644
--- a/extensions/telegram/src/bot-message-dispatch.ts
+++ b/extensions/telegram/src/bot-message-dispatch.ts
@@ -35,6 +35,7 @@ import type { TelegramStreamMode } from "./bot/types.js";
 import type { TelegramInlineButtons } from "./button-types.js";
 import { createTelegramDraftStream } from "./draft-stream.js";
 import { shouldSuppressLocalTelegramExecApprovalPrompt } from "./exec-approvals.js";
+import type { TelegramTransport } from "./fetch.js";
 import { renderTelegramHtmlText } from "./format.js";
 import {
   type ArchivedPreview,
@@ -111,6 +112,7 @@ type DispatchTelegramMessageParams = {
   textLimit: number;
   telegramCfg: TelegramAccountConfig;
   opts: Pick<TelegramBotOptions, "token">;
+  telegramTransport?: TelegramTransport;
 };
 
 type TelegramReasoningLevel = "off" | "on" | "stream";
@@ -148,6 +150,7 @@ export const dispatchTelegramMessage = async ({
   textLimit,
   telegramCfg,
   opts,
+  telegramTransport,
 }: DispatchTelegramMessageParams) => {
   const {
     ctxPayload,
@@ -457,6 +460,7 @@ export const dispatchTelegramMessage = async ({
     runtime,
     bot,
     mediaLocalRoots,
+    telegramTransport,
     replyToMode,
     textLimit,
     thread: threadSpec,
diff --git a/extensions/telegram/src/bot-message.ts b/extensions/telegram/src/bot-message.ts
index 0a5d44c65db..fc40b91009a 100644
--- a/extensions/telegram/src/bot-message.ts
+++ b/extensions/telegram/src/bot-message.ts
@@ -10,6 +10,7 @@ import {
 import { dispatchTelegramMessage } from "./bot-message-dispatch.js";
 import type { TelegramBotOptions } from "./bot.js";
 import type { TelegramContext, TelegramStreamMode } from "./bot/types.js";
+import type { TelegramTransport } from "./fetch.js";
 
 /** Dependencies injected once when creating the message processor. */
 type TelegramMessageProcessorDeps = Omit<
@@ -22,6 +23,7 @@ type TelegramMessageProcessorDeps = Omit<
   streamMode: TelegramStreamMode;
   textLimit: number;
   opts: Pick<TelegramBotOptions, "token">;
+  telegramTransport?: TelegramTransport;
 };
 
 export const createTelegramMessageProcessor = (deps: TelegramMessageProcessorDeps) => {
@@ -46,6 +48,7 @@ export const createTelegramMessageProcessor = (deps: TelegramMessageProcessorDep
     streamMode,
     textLimit,
     opts,
+    telegramTransport,
   } = deps;
 
   return async (
@@ -90,6 +93,7 @@ export const createTelegramMessageProcessor = (deps: TelegramMessageProcessorDep
         textLimit,
         telegramCfg,
         opts,
+        telegramTransport,
       });
     } catch (err) {
       runtime.error?.(danger(`telegram message processing failed: ${String(err)}`));
diff --git a/extensions/telegram/src/bot-native-commands.ts b/extensions/telegram/src/bot-native-commands.ts
index 7dd91f6ad63..c620e428bd6 100644
--- a/extensions/telegram/src/bot-native-commands.ts
+++ b/extensions/telegram/src/bot-native-commands.ts
@@ -140,6 +140,7 @@ type RegisterTelegramNativeCommandsParams = {
   ) => { groupConfig?: TelegramGroupConfig; topicConfig?: TelegramTopicConfig };
   shouldSkipUpdate: (ctx: TelegramUpdateKeyContext) => boolean;
   opts: { token: string };
+  telegramTransport?: TelegramTransport;
 };
 
 async function resolveTelegramCommandAuth(params: {
@@ -362,6 +363,7 @@ export const registerTelegramNativeCommands = ({
   resolveTelegramGroupConfig,
   shouldSkipUpdate,
   opts,
+  telegramTransport,
 }: RegisterTelegramNativeCommandsParams) => {
   const boundRoute =
     nativeEnabled && nativeSkillsEnabled
@@ -536,6 +538,7 @@ export const registerTelegramNativeCommands = ({
     runtime,
     bot,
     mediaLocalRoots: params.mediaLocalRoots,
+    telegramTransport,
     replyToMode,
     textLimit,
     thread: params.threadSpec,
diff --git a/extensions/telegram/src/bot.ts b/extensions/telegram/src/bot.ts
index a817e10cbac..35ba22cfd25 100644
--- a/extensions/telegram/src/bot.ts
+++ b/extensions/telegram/src/bot.ts
@@ -471,6 +471,7 @@ export function createTelegramBot(opts: TelegramBotOptions) {
     streamMode,
     textLimit,
     opts,
+    telegramTransport,
   });
 
   registerTelegramNativeCommands({
@@ -491,6 +492,7 @@ export function createTelegramBot(opts: TelegramBotOptions) {
     resolveTelegramGroupConfig,
     shouldSkipUpdate,
     opts,
+    telegramTransport,
   });
 
   registerTelegramHandlers({
diff --git a/extensions/telegram/src/bot/delivery.replies.ts b/extensions/telegram/src/bot/delivery.replies.ts
index 84d66fec12b..a473d44e4c5 100644
--- a/extensions/telegram/src/bot/delivery.replies.ts
+++ b/extensions/telegram/src/bot/delivery.replies.ts
@@ -23,6 +23,7 @@ import type { RuntimeEnv } from "../../../../src/runtime.js";
 import { loadWebMedia } from "../../../whatsapp/src/media.js";
 import type { TelegramInlineButtons } from "../button-types.js";
 import { splitTelegramCaption } from "../caption.js";
+import { shouldRetryTelegramIpv4Fallback, type TelegramTransport } from "../fetch.js";
 import {
   markdownToTelegramChunks,
   markdownToTelegramHtml,
@@ -234,6 +235,7 @@ async function deliverMediaReply(params: {
   thread?: TelegramThreadSpec | null;
   tableMode?: MarkdownTableMode;
   mediaLocalRoots?: readonly string[];
+  telegramTransport?: TelegramTransport;
   chunkText: ChunkTextFn;
   onVoiceRecording?: () => Promise<void> | void;
   linkPreview?: boolean;
@@ -250,7 +252,15 @@ async function deliverMediaReply(params: {
     const isFirstMedia = first;
     const media = await loadWebMedia(
       mediaUrl,
-      buildOutboundMediaLoadOptions({ mediaLocalRoots: params.mediaLocalRoots }),
+      buildOutboundMediaLoadOptions({
+        mediaLocalRoots: params.mediaLocalRoots,
+        fetchImpl: params.telegramTransport?.sourceFetch,
+        dispatcherPolicy: params.telegramTransport?.pinnedDispatcherPolicy,
+        fallbackDispatcherPolicy: params.telegramTransport?.fallbackPinnedDispatcherPolicy,
+        shouldRetryFetchError: params.telegramTransport
+          ? shouldRetryTelegramIpv4Fallback
+          : undefined,
+      }),
     );
     const kind = kindFromMime(media.contentType ?? undefined);
     const isGif = isGifMedia({
@@ -548,6 +558,7 @@ export async function deliverReplies(params: {
   runtime: RuntimeEnv;
   bot: Bot;
   mediaLocalRoots?: readonly string[];
+  telegramTransport?: TelegramTransport;
   replyToMode: ReplyToMode;
   textLimit: number;
   thread?: TelegramThreadSpec | null;
@@ -651,6 +662,7 @@ export async function deliverReplies(params: {
           thread: params.thread,
           tableMode: params.tableMode,
           mediaLocalRoots: params.mediaLocalRoots,
+          telegramTransport: params.telegramTransport,
           chunkText,
           onVoiceRecording: params.onVoiceRecording,
           linkPreview: params.linkPreview,
diff --git a/extensions/telegram/src/bot/delivery.test.ts b/extensions/telegram/src/bot/delivery.test.ts
index a1dce34dceb..045f41a511e 100644
--- a/extensions/telegram/src/bot/delivery.test.ts
+++ b/extensions/telegram/src/bot/delivery.test.ts
@@ -392,6 +392,44 @@ describe("deliverReplies", () => {
     });
   });
 
+  it("passes Telegram transport to remote media loading", async () => {
+    const runtime = createRuntime();
+    const sendPhoto = vi.fn().mockResolvedValue({
+      message_id: 13,
+      chat: { id: "123" },
+    });
+    const bot = createBot({ sendPhoto });
+    const sourceFetch = vi.fn() as unknown as typeof fetch;
+    const telegramTransport = {
+      fetch: sourceFetch,
+      sourceFetch,
+      pinnedDispatcherPolicy: {
+        mode: "explicit-proxy",
+        proxyUrl: "http://proxy.test:8080",
+      } as const,
+      fallbackPinnedDispatcherPolicy: { mode: "direct" } as const,
+    };
+
+    mockMediaLoad("photo.jpg", "image/jpeg", "image");
+
+    await deliverWith({
+      replies: [{ mediaUrl: "https://example.com/photo.jpg" }],
+      runtime,
+      bot,
+      telegramTransport,
+    });
+
+    expect(loadWebMedia).toHaveBeenCalledWith(
+      "https://example.com/photo.jpg",
+      expect.objectContaining({
+        fetchImpl: sourceFetch,
+        dispatcherPolicy: telegramTransport.pinnedDispatcherPolicy,
+        fallbackDispatcherPolicy: telegramTransport.fallbackPinnedDispatcherPolicy,
+        shouldRetryFetchError: expect.any(Function),
+      }),
+    );
+  });
+
   it("includes link_preview_options when linkPreview is false", async () => {
     const runtime = createRuntime();
     const sendMessage = vi.fn().mockResolvedValue({
diff --git a/extensions/telegram/src/send.proxy.test.ts b/extensions/telegram/src/send.proxy.test.ts
index 6c17b33fe38..6cb6bf2a2a5 100644
--- a/extensions/telegram/src/send.proxy.test.ts
+++ b/extensions/telegram/src/send.proxy.test.ts
@@ -3,6 +3,7 @@ import { beforeEach, describe, expect, it, vi } from "vitest";
 const { botApi, botCtorSpy } = vi.hoisted(() => ({
   botApi: {
     sendMessage: vi.fn(),
+    sendPhoto: vi.fn(),
     setMessageReaction: vi.fn(),
     deleteMessage: vi.fn(),
   },
@@ -17,8 +18,13 @@ const { makeProxyFetch } = vi.hoisted(() => ({
   makeProxyFetch: vi.fn(),
 }));
 
-const { resolveTelegramFetch } = vi.hoisted(() => ({
-  resolveTelegramFetch: vi.fn(),
+const { resolveTelegramTransport, shouldRetryTelegramIpv4Fallback } = vi.hoisted(() => ({
+  resolveTelegramTransport: vi.fn(),
+  shouldRetryTelegramIpv4Fallback: vi.fn(() => true),
+}));
+
+const { loadWebMedia } = vi.hoisted(() => ({
+  loadWebMedia: vi.fn(),
 }));
 
 vi.mock("../../../src/config/config.js", async (importOriginal) => {
@@ -33,13 +39,18 @@ vi.mock("./proxy.js", () => ({
   makeProxyFetch,
 }));
 
+vi.mock("../../whatsapp/src/media.js", () => ({
+  loadWebMedia,
+}));
+
 vi.mock("./fetch.js", () => ({
-  resolveTelegramFetch,
+  resolveTelegramTransport,
+  shouldRetryTelegramIpv4Fallback,
 }));
 
 vi.mock("grammy", () => ({
   Bot: class {
-    api = botApi;
+    api = { ...botApi };
     catch = vi.fn();
     constructor(
       public token: string,
@@ -61,21 +72,30 @@ import {
 describe("telegram proxy client", () => {
   const proxyUrl = "http://proxy.test:8080";
 
-  const prepareProxyFetch = () => {
+  const prepareProxyTransport = () => {
     const proxyFetch = vi.fn();
-    const fetchImpl = vi.fn();
+    const clientFetch = vi.fn();
+    const sourceFetch = vi.fn();
+    const transport = {
+      fetch: clientFetch as unknown as typeof fetch,
+      sourceFetch: sourceFetch as unknown as typeof fetch,
+      pinnedDispatcherPolicy: { mode: "explicit-proxy", proxyUrl } as const,
+      fallbackPinnedDispatcherPolicy: { mode: "direct" } as const,
+    };
     makeProxyFetch.mockReturnValue(proxyFetch as unknown as typeof fetch);
-    resolveTelegramFetch.mockReturnValue(fetchImpl as unknown as typeof fetch);
-    return { proxyFetch, fetchImpl };
+    resolveTelegramTransport.mockReturnValue(transport);
+    return { proxyFetch, transport };
   };
 
-  const expectProxyClient = (fetchImpl: ReturnType<typeof vi.fn>) => {
+  const expectProxyClient = (transport: ReturnType<typeof prepareProxyTransport>["transport"]) => {
     expect(makeProxyFetch).toHaveBeenCalledWith(proxyUrl);
-    expect(resolveTelegramFetch).toHaveBeenCalledWith(expect.any(Function), { network: undefined });
+    expect(resolveTelegramTransport).toHaveBeenCalledWith(expect.any(Function), {
+      network: undefined,
+    });
     expect(botCtorSpy).toHaveBeenCalledWith(
       "tok",
       expect.objectContaining({
-        client: expect.objectContaining({ fetch: fetchImpl }),
+        client: expect.objectContaining({ fetch: transport.fetch }),
       }),
     );
   };
@@ -86,16 +106,18 @@ describe("telegram proxy client", () => {
     botApi.sendMessage.mockResolvedValue({ message_id: 1, chat: { id: "123" } });
     botApi.setMessageReaction.mockResolvedValue(undefined);
     botApi.deleteMessage.mockResolvedValue(true);
+    botApi.sendPhoto.mockResolvedValue({ message_id: 2, chat: { id: "123" } });
     botCtorSpy.mockClear();
     loadConfig.mockReturnValue({
       channels: { telegram: { accounts: { foo: { proxy: proxyUrl } } } },
     });
     makeProxyFetch.mockClear();
-    resolveTelegramFetch.mockClear();
+    resolveTelegramTransport.mockClear();
+    loadWebMedia.mockReset();
   });
 
   it("reuses cached Telegram client options for repeated sends with same account transport settings", async () => {
-    const { fetchImpl } = prepareProxyFetch();
+    const { transport } = prepareProxyTransport();
     vi.stubEnv("VITEST", "");
     vi.stubEnv("NODE_ENV", "production");
 
@@ -103,20 +125,20 @@ describe("telegram proxy client", () => {
     await sendMessageTelegram("123", "second", { token: "tok", accountId: "foo" });
 
     expect(makeProxyFetch).toHaveBeenCalledTimes(1);
-    expect(resolveTelegramFetch).toHaveBeenCalledTimes(1);
+    expect(resolveTelegramTransport).toHaveBeenCalledTimes(1);
     expect(botCtorSpy).toHaveBeenCalledTimes(2);
     expect(botCtorSpy).toHaveBeenNthCalledWith(
       1,
       "tok",
       expect.objectContaining({
-        client: expect.objectContaining({ fetch: fetchImpl }),
+        client: expect.objectContaining({ fetch: transport.fetch }),
       }),
     );
     expect(botCtorSpy).toHaveBeenNthCalledWith(
       2,
       "tok",
       expect.objectContaining({
-        client: expect.objectContaining({ fetch: fetchImpl }),
+        client: expect.objectContaining({ fetch: transport.fetch }),
       }),
     );
   });
@@ -135,10 +157,36 @@ describe("telegram proxy client", () => {
       run: () => deleteMessageTelegram("123", "456", { token: "tok", accountId: "foo" }),
     },
   ])("uses proxy fetch for $name", async (testCase) => {
-    const { fetchImpl } = prepareProxyFetch();
+    const { transport } = prepareProxyTransport();
 
     await testCase.run();
 
-    expectProxyClient(fetchImpl);
+    expectProxyClient(transport);
+  });
+
+  it("uses proxy-aware transport for outbound media prefetch", async () => {
+    const { transport } = prepareProxyTransport();
+    loadWebMedia.mockResolvedValueOnce({
+      buffer: Buffer.from("image"),
+      contentType: "image/jpeg",
+      fileName: "photo.jpg",
+    });
+
+    await sendMessageTelegram("123", "caption", {
+      token: "tok",
+      accountId: "foo",
+      mediaUrl: "https://example.com/photo.jpg",
+    });
+
+    expectProxyClient(transport);
+    expect(loadWebMedia).toHaveBeenCalledWith(
+      "https://example.com/photo.jpg",
+      expect.objectContaining({
+        fetchImpl: transport.sourceFetch,
+        dispatcherPolicy: transport.pinnedDispatcherPolicy,
+        fallbackDispatcherPolicy: transport.fallbackPinnedDispatcherPolicy,
+        shouldRetryFetchError: expect.any(Function),
+      }),
+    );
   });
 });
diff --git a/extensions/telegram/src/send.ts b/extensions/telegram/src/send.ts
index e7d2c48e9fc..4509be33a6b 100644
--- a/extensions/telegram/src/send.ts
+++ b/extensions/telegram/src/send.ts
@@ -25,7 +25,11 @@ import { withTelegramApiErrorLogging } from "./api-logging.js";
 import { buildTelegramThreadParams, buildTypingThreadParams } from "./bot/helpers.js";
 import type { TelegramInlineButtons } from "./button-types.js";
 import { splitTelegramCaption } from "./caption.js";
-import { resolveTelegramFetch } from "./fetch.js";
+import {
+  resolveTelegramTransport,
+  shouldRetryTelegramIpv4Fallback,
+  type TelegramTransport,
+} from "./fetch.js";
 import { renderTelegramHtmlText, splitTelegramHtmlChunks } from "./format.js";
 import {
   isRecoverableTelegramNetworkError,
@@ -159,10 +163,12 @@ const CHAT_NOT_FOUND_RE = /400: Bad Request: chat not found/i;
 const sendLogger = createSubsystemLogger("telegram/send");
 const diagLogger = createSubsystemLogger("telegram/diagnostic");
 const telegramClientOptionsCache = new Map<string, ApiClientOptions | undefined>();
+const telegramTransportCache = new Map<string, TelegramTransport>();
 const MAX_TELEGRAM_CLIENT_OPTIONS_CACHE_SIZE = 64;
 
 export function resetTelegramClientOptionsCacheForTests(): void {
   telegramClientOptionsCache.clear();
+  telegramTransportCache.clear();
 }
 
 function createTelegramHttpLogger(cfg: ReturnType<typeof loadConfig>) {
@@ -183,18 +189,22 @@ function shouldUseTelegramClientOptionsCache(): boolean {
   return !process.env.VITEST && process.env.NODE_ENV !== "test";
 }
 
+function buildTelegramTransportCacheKey(account: ResolvedTelegramAccount): string {
+  const proxyKey = account.config.proxy?.trim() ?? "";
+  const autoSelectFamily = account.config.network?.autoSelectFamily;
+  const autoSelectFamilyKey =
+    typeof autoSelectFamily === "boolean" ? String(autoSelectFamily) : "default";
+  const dnsResultOrderKey = account.config.network?.dnsResultOrder ?? "default";
+  return `${account.accountId}::${proxyKey}::${autoSelectFamilyKey}::${dnsResultOrderKey}`;
+}
+
 function buildTelegramClientOptionsCacheKey(params: {
   account: ResolvedTelegramAccount;
   timeoutSeconds?: number;
 }): string {
-  const proxyKey = params.account.config.proxy?.trim() ?? "";
-  const autoSelectFamily = params.account.config.network?.autoSelectFamily;
-  const autoSelectFamilyKey =
-    typeof autoSelectFamily === "boolean" ? String(autoSelectFamily) : "default";
-  const dnsResultOrderKey = params.account.config.network?.dnsResultOrder ?? "default";
   const timeoutSecondsKey =
     typeof params.timeoutSeconds === "number" ? String(params.timeoutSeconds) : "default";
-  return `${params.account.accountId}::${proxyKey}::${autoSelectFamilyKey}::${dnsResultOrderKey}::${timeoutSecondsKey}`;
+  return `${buildTelegramTransportCacheKey(params.account)}::${timeoutSecondsKey}`;
 }
 
 function setCachedTelegramClientOptions(
@@ -211,8 +221,44 @@ function setCachedTelegramClientOptions(
   return clientOptions;
 }
 
+function setCachedTelegramTransport(
+  cacheKey: string,
+  transport: TelegramTransport,
+): TelegramTransport {
+  telegramTransportCache.set(cacheKey, transport);
+  if (telegramTransportCache.size > MAX_TELEGRAM_CLIENT_OPTIONS_CACHE_SIZE) {
+    const oldestKey = telegramTransportCache.keys().next().value;
+    if (oldestKey !== undefined) {
+      telegramTransportCache.delete(oldestKey);
+    }
+  }
+  return transport;
+}
+
+function resolveTelegramTransportForAccount(account: ResolvedTelegramAccount): TelegramTransport {
+  const cacheEnabled = shouldUseTelegramClientOptionsCache();
+  const cacheKey = cacheEnabled ? buildTelegramTransportCacheKey(account) : null;
+  if (cacheKey && telegramTransportCache.has(cacheKey)) {
+    const cached = telegramTransportCache.get(cacheKey);
+    if (cached) {
+      return cached;
+    }
+  }
+
+  const proxyUrl = account.config.proxy?.trim();
+  const proxyFetch = proxyUrl ? makeProxyFetch(proxyUrl) : undefined;
+  const transport = resolveTelegramTransport(proxyFetch, {
+    network: account.config.network,
+  });
+  if (cacheKey) {
+    return setCachedTelegramTransport(cacheKey, transport);
+  }
+  return transport;
+}
+
 function resolveTelegramClientOptions(
   account: ResolvedTelegramAccount,
+  transport: TelegramTransport = resolveTelegramTransportForAccount(account),
 ): ApiClientOptions | undefined {
   const timeoutSeconds =
     typeof account.config.timeoutSeconds === "number" &&
@@ -231,15 +277,12 @@ function resolveTelegramClientOptions(
     return telegramClientOptionsCache.get(cacheKey);
   }
 
-  const proxyUrl = account.config.proxy?.trim();
-  const proxyFetch = proxyUrl ? makeProxyFetch(proxyUrl) : undefined;
-  const fetchImpl = resolveTelegramFetch(proxyFetch, {
-    network: account.config.network,
-  });
   const clientOptions =
-    fetchImpl || timeoutSeconds
+    transport.fetch || timeoutSeconds
       ? {
-          ...(fetchImpl ? { fetch: fetchImpl as unknown as ApiClientOptions["fetch"] } : {}),
+          ...(transport.fetch
+            ? { fetch: transport.fetch as unknown as ApiClientOptions["fetch"] }
+            : {}),
           ...(timeoutSeconds ? { timeoutSeconds } : {}),
         }
       : undefined;
@@ -426,6 +469,7 @@ type TelegramApiContext = {
   cfg: ReturnType<typeof loadConfig>;
   account: ResolvedTelegramAccount;
   api: TelegramApi;
+  telegramTransport: TelegramTransport;
 };
 
 function resolveTelegramApiContext(opts: {
@@ -440,9 +484,10 @@ function resolveTelegramApiContext(opts: {
     accountId: opts.accountId,
   });
   const token = resolveToken(opts.token, account);
-  const client = resolveTelegramClientOptions(account);
+  const telegramTransport = resolveTelegramTransportForAccount(account);
+  const client = resolveTelegramClientOptions(account, telegramTransport);
   const api = (opts.api ?? new Bot(token, client ? { client } : undefined).api) as TelegramApi;
-  return { cfg, account, api };
+  return { cfg, account, api, telegramTransport };
 }
 
 type TelegramRequestWithDiag = <T>(
@@ -592,7 +637,7 @@ export async function sendMessageTelegram(
   text: string,
   opts: TelegramSendOpts = {},
 ): Promise<TelegramSendResult> {
-  const { cfg, account, api } = resolveTelegramApiContext(opts);
+  const { cfg, account, api, telegramTransport } = resolveTelegramApiContext(opts);
   const target = parseTelegramTarget(to);
   const chatId = await resolveAndPersistChatId({
     cfg,
@@ -766,6 +811,10 @@ export async function sendMessageTelegram(
         maxBytes: mediaMaxBytes,
         mediaLocalRoots: opts.mediaLocalRoots,
         optimizeImages: opts.forceDocument ? false : undefined,
+        fetchImpl: telegramTransport.sourceFetch,
+        dispatcherPolicy: telegramTransport.pinnedDispatcherPolicy,
+        fallbackDispatcherPolicy: telegramTransport.fallbackPinnedDispatcherPolicy,
+        shouldRetryFetchError: shouldRetryTelegramIpv4Fallback,
       }),
     );
     const kind = kindFromMime(media.contentType ?? undefined);
diff --git a/extensions/whatsapp/src/media.ts b/extensions/whatsapp/src/media.ts
index 2b297ef8907..23d59df82fd 100644
--- a/extensions/whatsapp/src/media.ts
+++ b/extensions/whatsapp/src/media.ts
@@ -3,9 +3,9 @@ import path from "node:path";
 import { fileURLToPath } from "node:url";
 import { logVerbose, shouldLogVerbose } from "../../../src/globals.js";
 import { SafeOpenError, readLocalFileSafely } from "../../../src/infra/fs-safe.js";
-import type { SsrFPolicy } from "../../../src/infra/net/ssrf.js";
+import type { PinnedDispatcherPolicy, SsrFPolicy } from "../../../src/infra/net/ssrf.js";
 import { type MediaKind, maxBytesForKind } from "../../../src/media/constants.js";
-import { fetchRemoteMedia } from "../../../src/media/fetch.js";
+import { fetchRemoteMedia, type FetchLike } from "../../../src/media/fetch.js";
 import {
   convertHeicToJpeg,
   hasAlphaChannel,
@@ -27,6 +27,10 @@ type WebMediaOptions = {
   maxBytes?: number;
   optimizeImages?: boolean;
   ssrfPolicy?: SsrFPolicy;
+  fetchImpl?: FetchLike;
+  dispatcherPolicy?: PinnedDispatcherPolicy;
+  fallbackDispatcherPolicy?: PinnedDispatcherPolicy;
+  shouldRetryFetchError?: (error: unknown) => boolean;
   /** Allowed root directories for local path reads. "any" is deprecated; prefer sandboxValidated + readFile. */
   localRoots?: readonly string[] | "any";
   /** Caller already validated the local path (sandbox/other guards); requires readFile override. */
@@ -36,7 +40,14 @@ type WebMediaOptions = {
 
 function resolveWebMediaOptions(params: {
   maxBytesOrOptions?: number | WebMediaOptions;
-  options?: { ssrfPolicy?: SsrFPolicy; localRoots?: readonly string[] | "any" };
+  options?: {
+    ssrfPolicy?: SsrFPolicy;
+    fetchImpl?: FetchLike;
+    dispatcherPolicy?: PinnedDispatcherPolicy;
+    fallbackDispatcherPolicy?: PinnedDispatcherPolicy;
+    shouldRetryFetchError?: (error: unknown) => boolean;
+    localRoots?: readonly string[] | "any";
+  };
   optimizeImages: boolean;
 }): WebMediaOptions {
   if (typeof params.maxBytesOrOptions === "number" || params.maxBytesOrOptions === undefined) {
@@ -44,6 +55,10 @@ function resolveWebMediaOptions(params: {
       maxBytes: params.maxBytesOrOptions,
       optimizeImages: params.optimizeImages,
       ssrfPolicy: params.options?.ssrfPolicy,
+      fetchImpl: params.options?.fetchImpl,
+      dispatcherPolicy: params.options?.dispatcherPolicy,
+      fallbackDispatcherPolicy: params.options?.fallbackDispatcherPolicy,
+      shouldRetryFetchError: params.options?.shouldRetryFetchError,
       localRoots: params.options?.localRoots,
     };
   }
@@ -238,6 +253,10 @@ async function loadWebMediaInternal(
     maxBytes,
     optimizeImages = true,
     ssrfPolicy,
+    fetchImpl,
+    dispatcherPolicy,
+    fallbackDispatcherPolicy,
+    shouldRetryFetchError,
     localRoots,
     sandboxValidated = false,
     readFile: readFileOverride,
@@ -331,7 +350,15 @@ async function loadWebMediaInternal(
         : optimizeImages
           ? Math.max(maxBytes, defaultFetchCap)
           : maxBytes;
-    const fetched = await fetchRemoteMedia({ url: mediaUrl, maxBytes: fetchCap, ssrfPolicy });
+    const fetched = await fetchRemoteMedia({
+      url: mediaUrl,
+      fetchImpl,
+      maxBytes: fetchCap,
+      ssrfPolicy,
+      dispatcherPolicy,
+      fallbackDispatcherPolicy,
+      shouldRetryFetchError,
+    });
     const { buffer, contentType, fileName } = fetched;
     const kind = kindFromMime(contentType);
     return await clampAndFinalize({ buffer, contentType, kind, fileName });
@@ -404,7 +431,14 @@ async function loadWebMediaInternal(
 export async function loadWebMedia(
   mediaUrl: string,
   maxBytesOrOptions?: number | WebMediaOptions,
-  options?: { ssrfPolicy?: SsrFPolicy; localRoots?: readonly string[] | "any" },
+  options?: {
+    ssrfPolicy?: SsrFPolicy;
+    fetchImpl?: FetchLike;
+    dispatcherPolicy?: PinnedDispatcherPolicy;
+    fallbackDispatcherPolicy?: PinnedDispatcherPolicy;
+    shouldRetryFetchError?: (error: unknown) => boolean;
+    localRoots?: readonly string[] | "any";
+  },
 ): Promise<WebMediaResult> {
   return await loadWebMediaInternal(
     mediaUrl,
@@ -415,7 +449,14 @@ export async function loadWebMedia(
 export async function loadWebMediaRaw(
   mediaUrl: string,
   maxBytesOrOptions?: number | WebMediaOptions,
-  options?: { ssrfPolicy?: SsrFPolicy; localRoots?: readonly string[] | "any" },
+  options?: {
+    ssrfPolicy?: SsrFPolicy;
+    fetchImpl?: FetchLike;
+    dispatcherPolicy?: PinnedDispatcherPolicy;
+    fallbackDispatcherPolicy?: PinnedDispatcherPolicy;
+    shouldRetryFetchError?: (error: unknown) => boolean;
+    localRoots?: readonly string[] | "any";
+  },
 ): Promise<WebMediaResult> {
   return await loadWebMediaInternal(
     mediaUrl,
diff --git a/extensions/whatsapp/src/monitor-inbox.allows-messages-from-senders-allowfrom-list.test.ts b/extensions/whatsapp/src/monitor-inbox.allows-messages-from-senders-allowfrom-list.test.ts
index 545a010ed50..c0902b3d113 100644
--- a/extensions/whatsapp/src/monitor-inbox.allows-messages-from-senders-allowfrom-list.test.ts
+++ b/extensions/whatsapp/src/monitor-inbox.allows-messages-from-senders-allowfrom-list.test.ts
@@ -252,7 +252,7 @@ describe("web monitor inbox", () => {
     });
   });
 
-  it("handles append messages by marking them read but skipping auto-reply", async () => {
+  it("handles stale append messages by marking them read but skipping auto-reply", async () => {
     const { onMessage, listener, sock } = await openInboxMonitor();
 
     const upsert = {
@@ -265,7 +265,7 @@ describe("web monitor inbox", () => {
             remoteJid: "999@s.whatsapp.net",
           },
           message: { conversation: "old message" },
-          messageTimestamp: nowSeconds(),
+          messageTimestamp: nowSeconds(-300_000),
           pushName: "History Sender",
         },
       ],
@@ -284,7 +284,7 @@ describe("web monitor inbox", () => {
       },
     ]);
 
-    // Verify it WAS NOT passed to onMessage
+    // Verify stale history sync messages are not passed to onMessage
     expect(onMessage).not.toHaveBeenCalled();
 
     await listener.close();
diff --git a/src/media/load-options.test.ts b/src/media/load-options.test.ts
index 52e61e59cc7..1da7a0430b4 100644
--- a/src/media/load-options.test.ts
+++ b/src/media/load-options.test.ts
@@ -22,4 +22,25 @@ describe("media load options", () => {
       localRoots: ["/tmp/workspace"],
     });
   });
+
+  it("preserves custom fetch transport options", () => {
+    const fetchImpl = (() => Promise.resolve(new Response())) as typeof fetch;
+    const dispatcherPolicy = { mode: "direct" } as const;
+    const fallbackDispatcherPolicy = { mode: "env-proxy" } as const;
+    const shouldRetryFetchError = () => true;
+
+    expect(
+      buildOutboundMediaLoadOptions({
+        fetchImpl,
+        dispatcherPolicy,
+        fallbackDispatcherPolicy,
+        shouldRetryFetchError,
+      }),
+    ).toEqual({
+      fetchImpl,
+      dispatcherPolicy,
+      fallbackDispatcherPolicy,
+      shouldRetryFetchError,
+    });
+  });
 });
diff --git a/src/media/load-options.ts b/src/media/load-options.ts
index da4545ae10e..a82a5f40ca0 100644
--- a/src/media/load-options.ts
+++ b/src/media/load-options.ts
@@ -1,14 +1,24 @@
+import type { PinnedDispatcherPolicy } from "../infra/net/ssrf.js";
+import type { FetchLike } from "./fetch.js";
+
+export type OutboundMediaFetchOptions = {
+  fetchImpl?: FetchLike;
+  dispatcherPolicy?: PinnedDispatcherPolicy;
+  fallbackDispatcherPolicy?: PinnedDispatcherPolicy;
+  shouldRetryFetchError?: (error: unknown) => boolean;
+};
+
 export type OutboundMediaLoadParams = {
   maxBytes?: number;
   mediaLocalRoots?: readonly string[];
   optimizeImages?: boolean;
-};
+} & OutboundMediaFetchOptions;
 
 export type OutboundMediaLoadOptions = {
   maxBytes?: number;
   localRoots?: readonly string[];
   optimizeImages?: boolean;
-};
+} & OutboundMediaFetchOptions;
 
 export function resolveOutboundMediaLocalRoots(
   mediaLocalRoots?: readonly string[],
@@ -24,5 +34,13 @@ export function buildOutboundMediaLoadOptions(
     ...(params.maxBytes !== undefined ? { maxBytes: params.maxBytes } : {}),
     ...(localRoots ? { localRoots } : {}),
     ...(params.optimizeImages !== undefined ? { optimizeImages: params.optimizeImages } : {}),
+    ...(params.fetchImpl ? { fetchImpl: params.fetchImpl } : {}),
+    ...(params.dispatcherPolicy ? { dispatcherPolicy: params.dispatcherPolicy } : {}),
+    ...(params.fallbackDispatcherPolicy
+      ? { fallbackDispatcherPolicy: params.fallbackDispatcherPolicy }
+      : {}),
+    ...(params.shouldRetryFetchError
+      ? { shouldRetryFetchError: params.shouldRetryFetchError }
+      : {}),
   };
 }