diff --git a/src/telegram/bot-native-commands.ts b/src/telegram/bot-native-commands.ts
index c57e1097485..17958daa289 100644
--- a/src/telegram/bot-native-commands.ts
+++ b/src/telegram/bot-native-commands.ts
@@ -595,17 +595,6 @@ export const registerTelegramNativeCommands = ({
             return;
           }
           const { threadSpec, route, mediaLocalRoots, tableMode, chunkMode } = runtimeContext;
-          const deliveryBaseOptions = buildCommandDeliveryBaseOptions({
-            chatId,
-            accountId: route.accountId,
-            sessionKeyForInternalHooks: route.sessionKey,
-            mirrorIsGroup: isGroup,
-            mirrorGroupId: isGroup ? String(chatId) : undefined,
-            mediaLocalRoots,
-            threadSpec,
-            tableMode,
-            chunkMode,
-          });
           const threadParams = buildTelegramThreadParams(threadSpec) ?? {};
 
           const commandDefinition = findCommandByNativeName(command.name, "telegram");
@@ -680,6 +669,17 @@ export const registerTelegramNativeCommands = ({
               userId: String(senderId || chatId),
               targetSessionKey: sessionKey,
             });
+          const deliveryBaseOptions = buildCommandDeliveryBaseOptions({
+            chatId,
+            accountId: route.accountId,
+            sessionKeyForInternalHooks: commandSessionKey,
+            mirrorIsGroup: isGroup,
+            mirrorGroupId: isGroup ? String(chatId) : undefined,
+            mediaLocalRoots,
+            threadSpec,
+            tableMode,
+            chunkMode,
+          });
           const conversationLabel = isGroup
             ? msg.chat.title
               ? `${msg.chat.title} id:${chatId}`
diff --git a/src/telegram/bot/delivery.test.ts b/src/telegram/bot/delivery.test.ts
index b8eb6274409..c21e55ccf6c 100644
--- a/src/telegram/bot/delivery.test.ts
+++ b/src/telegram/bot/delivery.test.ts
@@ -258,6 +258,37 @@ describe("deliverReplies", () => {
     expect(triggerInternalHook).not.toHaveBeenCalled();
   });
 
+  it("emits internal message:sent with success=false on delivery failure", async () => {
+    const runtime = createRuntime(false);
+    const sendMessage = vi.fn().mockRejectedValue(new Error("network error"));
+    const bot = createBot({ sendMessage });
+
+    await expect(
+      deliverWith({
+        sessionKeyForInternalHooks: "agent:test:telegram:123",
+        replies: [{ text: "hello" }],
+        runtime,
+        bot,
+      }),
+    ).rejects.toThrow("network error");
+
+    expect(triggerInternalHook).toHaveBeenCalledWith(
+      expect.objectContaining({
+        type: "message",
+        action: "sent",
+        sessionKey: "agent:test:telegram:123",
+        context: expect.objectContaining({
+          to: "123",
+          content: "hello",
+          success: false,
+          error: "network error",
+          channelId: "telegram",
+          conversationId: "123",
+        }),
+      }),
+    );
+  });
+
   it("passes media metadata to message_sending hooks", async () => {
     messageHookRunner.hasHooks.mockImplementation((name: string) => name === "message_sending");