diff --git a/gateway/platforms/webhook.py b/gateway/platforms/webhook.py
index 32c6e8109bd9..59af2e01966d 100644
--- a/gateway/platforms/webhook.py
+++ b/gateway/platforms/webhook.py
@@ -916,10 +916,28 @@ async def _deliver_cross_platform(
                     error=f"No chat_id or home channel for {platform_name}",
                 )
 
-        # Pass thread_id from deliver_extra so Telegram forum topics work
-        metadata = None
+        # Pass thread_id from deliver_extra so Telegram forum topics work.
+        # Also forward the Telegram DM-topic routing signals the adapter needs
+        # to satisfy the fail-loud anchor-required guard added in PR #32270:
+        # without one of telegram_reply_to_message_id, direct_messages_topic_id,
+        # or telegram_dm_topic_created_for_send, a private DM with a thread_id
+        # is rejected with "requires a reply anchor". Webhook routes have no
+        # other channel to express the opt-out, so plumb the keys straight
+        # through from deliver_extra.
+        metadata: Optional[Dict[str, Any]] = None
         thread_id = extra.get("message_thread_id") or extra.get("thread_id")
         if thread_id:
             metadata = {"thread_id": thread_id}
+        for key in (
+            "telegram_reply_to_message_id",
+            "telegram_dm_topic_created_for_send",
+            "telegram_dm_topic_reply_fallback",
+            "direct_messages_topic_id",
+        ):
+            value = extra.get(key)
+            if value is not None:
+                if metadata is None:
+                    metadata = {}
+                metadata[key] = value
 
         return await adapter.send(chat_id, content, metadata=metadata)
diff --git a/tests/gateway/test_webhook_adapter.py b/tests/gateway/test_webhook_adapter.py
index 606bd80e46e8..e81098294b12 100644
--- a/tests/gateway/test_webhook_adapter.py
+++ b/tests/gateway/test_webhook_adapter.py
@@ -956,6 +956,93 @@ async def test_no_thread_id_sends_no_metadata(self):
             "12345", "hello", metadata=None
         )
 
+    @pytest.mark.asyncio
+    async def test_telegram_reply_to_message_id_forwarded(self):
+        """telegram_reply_to_message_id in deliver_extra reaches metadata so
+        the Telegram adapter's anchor-required guard accepts a DM-topic send."""
+        adapter, mock_target = self._setup_adapter_with_mock_target()
+        delivery = {
+            "deliver_extra": {
+                "chat_id": "12345",
+                "message_thread_id": "888",
+                "telegram_reply_to_message_id": "42",
+            }
+        }
+        await adapter._deliver_cross_platform("telegram", "hello", delivery)
+        mock_target.send.assert_awaited_once_with(
+            "12345",
+            "hello",
+            metadata={"thread_id": "888", "telegram_reply_to_message_id": "42"},
+        )
+
+    @pytest.mark.asyncio
+    async def test_telegram_dm_topic_opt_out_flags_forwarded(self):
+        """telegram_dm_topic_created_for_send and direct_messages_topic_id are
+        forwarded so a webhook route can opt out of the reply-anchor guard
+        when sending to a true Bot-API DM topic."""
+        adapter, mock_target = self._setup_adapter_with_mock_target()
+        delivery = {
+            "deliver_extra": {
+                "chat_id": "12345",
+                "message_thread_id": "888",
+                "telegram_dm_topic_created_for_send": True,
+                "direct_messages_topic_id": "777",
+            }
+        }
+        await adapter._deliver_cross_platform("telegram", "hello", delivery)
+        mock_target.send.assert_awaited_once_with(
+            "12345",
+            "hello",
+            metadata={
+                "thread_id": "888",
+                "telegram_dm_topic_created_for_send": True,
+                "direct_messages_topic_id": "777",
+            },
+        )
+
+    @pytest.mark.asyncio
+    async def test_telegram_reply_fallback_marker_forwarded(self):
+        """telegram_dm_topic_reply_fallback combined with the reply anchor lets
+        the Telegram adapter pick its reply_to_mode-aware send path."""
+        adapter, mock_target = self._setup_adapter_with_mock_target()
+        delivery = {
+            "deliver_extra": {
+                "chat_id": "12345",
+                "message_thread_id": "888",
+                "telegram_dm_topic_reply_fallback": True,
+                "telegram_reply_to_message_id": "42",
+            }
+        }
+        await adapter._deliver_cross_platform("telegram", "hello", delivery)
+        mock_target.send.assert_awaited_once_with(
+            "12345",
+            "hello",
+            metadata={
+                "thread_id": "888",
+                "telegram_dm_topic_reply_fallback": True,
+                "telegram_reply_to_message_id": "42",
+            },
+        )
+
+    @pytest.mark.asyncio
+    async def test_dm_topic_keys_without_thread_id(self):
+        """deliver_extra may carry the opt-out flags without a thread_id (e.g.
+        a DM topic created by the route handler upstream). The metadata dict
+        still contains the forwarded keys."""
+        adapter, mock_target = self._setup_adapter_with_mock_target()
+        delivery = {
+            "deliver_extra": {
+                "chat_id": "12345",
+                "telegram_dm_topic_created_for_send": True,
+            }
+        }
+        await adapter._deliver_cross_platform("telegram", "hello", delivery)
+        mock_target.send.assert_awaited_once_with(
+            "12345",
+            "hello",
+            metadata={"telegram_dm_topic_created_for_send": True},
+        )
+
 
 class TestInsecureNoAuthSafetyRail:
     """connect() refuses to start when INSECURE_NO_AUTH is combined with a