diff --git a/nanobot/channels/telegram.py b/nanobot/channels/telegram.py
index d55c1a02..40ba71ad 100644
--- a/nanobot/channels/telegram.py
+++ b/nanobot/channels/telegram.py
@@ -520,8 +520,13 @@ class TelegramChannel(BaseChannel):
         # Send text content
         if msg.content and msg.content != "[empty message]":
             render_as_blockquote = bool(msg.metadata.get("_tool_hint"))
-            chunks = split_message(msg.content, TELEGRAM_MAX_MESSAGE_LEN)
-            reply_markup = self._build_keyboard(msg.buttons) if getattr(msg, 'buttons', None) else None
+            buttons = getattr(msg, "buttons", None) or []
+            reply_markup = self._build_keyboard(buttons) if buttons else None
+            text = msg.content
+            # Fallback: no native keyboard → splice labels into the message so the choices survive.
+            if buttons and reply_markup is None:
+                text = f"{text}\n\n{self._buttons_as_text(buttons)}"
+            chunks = split_message(text, TELEGRAM_MAX_MESSAGE_LEN)
             for i, chunk in enumerate(chunks):
                 is_last = (i == len(chunks) - 1)
                 await self._send_text(
@@ -1205,6 +1210,11 @@ class TelegramChannel(BaseChannel):
         ]
         return InlineKeyboardMarkup(keyboard)
 
+    @staticmethod
+    def _buttons_as_text(buttons: list[list[str]]) -> str:
+        # Buttons are semantic options; when we can't render a keyboard, the user still needs to see them.
+        return "\n".join(" ".join(f"[{label}]" for label in row) for row in buttons if row)
+
     async def _on_callback_query(self, update: Update, context: ContextTypes.DEFAULT_TYPE) -> None:
         """Handle inline keyboard button clicks (callback queries)."""
         if not update.callback_query or not update.effective_user:
diff --git a/tests/channels/test_telegram_channel.py b/tests/channels/test_telegram_channel.py
index 5480b878..a9fad504 100644
--- a/tests/channels/test_telegram_channel.py
+++ b/tests/channels/test_telegram_channel.py
@@ -1617,3 +1617,64 @@ def test_build_keyboard_respects_inline_keyboards_flag() -> None:
     assert [[b.text for b in row] for row in rows] == [["Yes", "No"], ["Cancel"]]
     # callback_data mirrors label so _on_callback_query can echo the tap back.
     assert rows[0][0].callback_data == "Yes"
+
+
+def test_buttons_as_text_format_preserves_rows_and_labels() -> None:
+    # Canonical shape: one row per line, labels bracketed. Layout survives the fallback.
+    assert TelegramChannel._buttons_as_text([["Yes", "No"], ["Cancel"]]) == "[Yes] [No]\n[Cancel]"
+    assert TelegramChannel._buttons_as_text([["Only"]]) == "[Only]"
+    assert TelegramChannel._buttons_as_text([[], ["A"]]) == "[A]"  # empty rows skipped
+
+
+@pytest.mark.asyncio
+async def test_send_falls_back_buttons_to_inline_text_when_flag_off() -> None:
+    """Buttons are semantic options; with ``inline_keyboards=False`` we must
+    splice labels into the text so users still see the choices. Silent-drop
+    was the pre-fallback bug — the agent got a success reply while the user
+    saw a question with no options."""
+    channel = TelegramChannel(
+        TelegramConfig(enabled=True, token="123:abc", allow_from=["*"], inline_keyboards=False),
+        MessageBus(),
+    )
+    channel._app = _FakeApp(lambda: None)
+
+    await channel.send(
+        OutboundMessage(
+            channel="telegram",
+            chat_id="123",
+            content="Proceed?",
+            buttons=[["Yes", "No"], ["Cancel"]],
+        )
+    )
+
+    assert len(channel._app.bot.sent_messages) == 1
+    sent = channel._app.bot.sent_messages[0]
+    assert sent.get("reply_markup") is None
+    assert "Proceed?" in sent["text"]
+    assert "[Yes] [No]" in sent["text"]
+    assert "[Cancel]" in sent["text"]
+
+
+@pytest.mark.asyncio
+async def test_send_uses_native_keyboard_when_flag_on() -> None:
+    """With the flag on, the content stays clean and buttons ride in ``reply_markup``."""
+    from telegram import InlineKeyboardMarkup
+
+    channel = TelegramChannel(
+        TelegramConfig(enabled=True, token="123:abc", allow_from=["*"], inline_keyboards=True),
+        MessageBus(),
+    )
+    channel._app = _FakeApp(lambda: None)
+
+    await channel.send(
+        OutboundMessage(
+            channel="telegram",
+            chat_id="123",
+            content="Proceed?",
+            buttons=[["Yes", "No"]],
+        )
+    )
+
+    sent = channel._app.bot.sent_messages[0]
+    assert isinstance(sent.get("reply_markup"), InlineKeyboardMarkup)
+    assert "[Yes]" not in sent["text"]  # native keyboard owns the rendering