diff --git a/gateway/platforms/telegram.py b/gateway/platforms/telegram.py
index 9e78282be..524324c8d 100644
--- a/gateway/platforms/telegram.py
+++ b/gateway/platforms/telegram.py
@@ -601,6 +601,12 @@ class TelegramAdapter(BasePlatformAdapter):
                 )
             else:
                 # ── Polling mode (default) ───────────────────────────
+                # Clear any stale webhook first so polling doesn't inherit a
+                # previous webhook registration and silently stop receiving updates.
+                delete_webhook = getattr(self._bot, "delete_webhook", None)
+                if callable(delete_webhook):
+                    await delete_webhook(drop_pending_updates=False)
+
                 loop = asyncio.get_running_loop()
 
                 def _polling_error_callback(error: Exception) -> None:
@@ -856,6 +862,21 @@ class TelegramAdapter(BasePlatformAdapter):
                             await asyncio.sleep(wait)
                         else:
                             raise
+                    except Exception as send_err:
+                        retry_after = getattr(send_err, "retry_after", None)
+                        if retry_after is not None or "retry after" in str(send_err).lower():
+                            if _send_attempt < 2:
+                                wait = float(retry_after) if retry_after is not None else 1.0
+                                logger.warning(
+                                    "[%s] Telegram flood control on send (attempt %d/3), retrying in %.1fs: %s",
+                                    self.name,
+                                    _send_attempt + 1,
+                                    wait,
+                                    send_err,
+                                )
+                                await asyncio.sleep(wait)
+                                continue
+                        raise
                 message_ids.append(str(msg.message_id))
             
             return SendResult(
diff --git a/tests/gateway/test_telegram_conflict.py b/tests/gateway/test_telegram_conflict.py
index 9f1074648..7a480d9fc 100644
--- a/tests/gateway/test_telegram_conflict.py
+++ b/tests/gateway/test_telegram_conflict.py
@@ -80,7 +80,7 @@ async def test_polling_conflict_retries_before_fatal(monkeypatch):
         stop=AsyncMock(),
         running=True,
     )
-    bot = SimpleNamespace(set_my_commands=AsyncMock())
+    bot = SimpleNamespace(set_my_commands=AsyncMock(), delete_webhook=AsyncMock())
     app = SimpleNamespace(
         bot=bot,
         updater=updater,
@@ -99,6 +99,7 @@ async def test_polling_conflict_retries_before_fatal(monkeypatch):
     ok = await adapter.connect()
 
     assert ok is True
+    bot.delete_webhook.assert_awaited_once_with(drop_pending_updates=False)
     assert callable(captured["error_callback"])
 
     conflict = type("Conflict", (Exception,), {})
@@ -153,7 +154,7 @@ async def test_polling_conflict_becomes_fatal_after_retries(monkeypatch):
         stop=AsyncMock(),
         running=True,
     )
-    bot = SimpleNamespace(set_my_commands=AsyncMock())
+    bot = SimpleNamespace(set_my_commands=AsyncMock(), delete_webhook=AsyncMock())
     app = SimpleNamespace(
         bot=bot,
         updater=updater,
@@ -208,7 +209,7 @@ async def test_connect_marks_retryable_fatal_error_for_startup_network_failure(m
     builder = MagicMock()
     builder.token.return_value = builder
     app = SimpleNamespace(
-        bot=SimpleNamespace(),
+        bot=SimpleNamespace(delete_webhook=AsyncMock(), set_my_commands=AsyncMock()),
         updater=SimpleNamespace(),
         add_handler=MagicMock(),
         initialize=AsyncMock(side_effect=RuntimeError("Temporary failure in name resolution")),
@@ -225,6 +226,49 @@ async def test_connect_marks_retryable_fatal_error_for_startup_network_failure(m
     assert "Temporary failure in name resolution" in adapter.fatal_error_message
 
 
+@pytest.mark.asyncio
+async def test_connect_clears_webhook_before_polling(monkeypatch):
+    adapter = TelegramAdapter(PlatformConfig(enabled=True, token="***"))
+
+    monkeypatch.setattr(
+        "gateway.status.acquire_scoped_lock",
+        lambda scope, identity, metadata=None: (True, None),
+    )
+    monkeypatch.setattr(
+        "gateway.status.release_scoped_lock",
+        lambda scope, identity: None,
+    )
+
+    updater = SimpleNamespace(
+        start_polling=AsyncMock(),
+        stop=AsyncMock(),
+        running=True,
+    )
+    bot = SimpleNamespace(
+        delete_webhook=AsyncMock(),
+        set_my_commands=AsyncMock(),
+    )
+    app = SimpleNamespace(
+        bot=bot,
+        updater=updater,
+        add_handler=MagicMock(),
+        initialize=AsyncMock(),
+        start=AsyncMock(),
+    )
+    builder = MagicMock()
+    builder.token.return_value = builder
+    builder.build.return_value = app
+    monkeypatch.setattr(
+        "gateway.platforms.telegram.Application",
+        SimpleNamespace(builder=MagicMock(return_value=builder)),
+    )
+
+    ok = await adapter.connect()
+
+    assert ok is True
+    bot.delete_webhook.assert_awaited_once_with(drop_pending_updates=False)
+
+
 @pytest.mark.asyncio
 async def test_disconnect_skips_inactive_updater_and_app(monkeypatch):
     adapter = TelegramAdapter(PlatformConfig(enabled=True, token="***"))
diff --git a/tests/gateway/test_telegram_thread_fallback.py b/tests/gateway/test_telegram_thread_fallback.py
index 735744e4e..fee1dcc80 100644
--- a/tests/gateway/test_telegram_thread_fallback.py
+++ b/tests/gateway/test_telegram_thread_fallback.py
@@ -37,6 +37,12 @@ class FakeTimedOut(FakeNetworkError):
     pass
 
 
+class FakeRetryAfter(Exception):
+    def __init__(self, seconds):
+        super().__init__(f"Retry after {seconds}")
+        self.retry_after = seconds
+
+
 # Build a fake telegram module tree so the adapter's internal imports work
 _fake_telegram = types.ModuleType("telegram")
 _fake_telegram_error = types.ModuleType("telegram.error")
@@ -230,3 +236,25 @@ async def test_thread_fallback_only_fires_once():
     # Second chunk: should use thread_id=None directly (effective_thread_id
     # was cleared per-chunk but the metadata doesn't change between chunks)
     # The key point: the message was delivered despite the invalid thread
+
+
+@pytest.mark.asyncio
+async def test_send_retries_retry_after_errors():
+    """Telegram flood control should back off and retry instead of failing fast."""
+    adapter = _make_adapter()
+
+    attempt = [0]
+
+    async def mock_send_message(**kwargs):
+        attempt[0] += 1
+        if attempt[0] == 1:
+            raise FakeRetryAfter(2)
+        return SimpleNamespace(message_id=300)
+
+    adapter._bot = SimpleNamespace(send_message=mock_send_message)
+
+    result = await adapter.send(chat_id="123", content="test message")
+
+    assert result.success is True
+    assert result.message_id == "300"
+    assert attempt[0] == 2