diff --git a/app/CLAUDE.md b/app/CLAUDE.md
index dd01b098..f30e594a 100644
--- a/app/CLAUDE.md
+++ b/app/CLAUDE.md
@@ -113,6 +113,8 @@ broadcast_health(radio_connected=True, serial_port="/dev/ttyUSB0")
 - Checks connection every 5 seconds
 - Broadcasts `health` event on status change
 - Attempts automatic reconnection when connection lost
+- **Re-registers event handlers after successful auto-reconnect** (critical for message delivery)
+- Resilient to transient errors (logs and continues rather than crashing)
 - Supports manual reconnection via `POST /api/radio/reconnect`
 
 ```python
@@ -126,6 +128,33 @@ await radio_manager.start_connection_monitor()
 await radio_manager.stop_connection_monitor()
 ```
 
+### Message Polling
+
+Periodic message polling serves as a fallback for platforms where push events are unreliable.
+Use `pause_polling()` to temporarily suspend polling during operations that need exclusive
+radio access (e.g., repeater CLI commands):
+
+```python
+from app.radio_sync import pause_polling, is_polling_paused
+
+# Pause polling during sensitive operations (supports nesting)
+async with pause_polling():
+    # Polling is paused here
+    await do_repeater_operation()
+
+    async with pause_polling():
+        # Still paused (nested)
+        await do_another_operation()
+
+    # Still paused (outer context active)
+
+# Polling resumes when all contexts exit
+
+# Check current state
+if is_polling_paused():
+    print("Polling is currently paused")
+```
+
 ## Database Schema
 
 ```sql
diff --git a/app/radio.py b/app/radio.py
index 003f9b39..98cc2d4e 100644
--- a/app/radio.py
+++ b/app/radio.py
@@ -210,26 +210,40 @@ class RadioManager:
             from app.websocket import broadcast_health
 
             while True:
-                await asyncio.sleep(5)  # Check every 5 seconds
+                try:
+                    await asyncio.sleep(5)  # Check every 5 seconds
 
-                current_connected = self.is_connected
+                    current_connected = self.is_connected
 
-                # Detect status change
-                if self._last_connected and not current_connected:
-                    # Connection lost
-                    logger.warning("Radio connection lost, broadcasting status change")
-                    broadcast_health(False, self._port)
-                    self._last_connected = False
+                    # Detect status change
+                    if self._last_connected and not current_connected:
+                        # Connection lost
+                        logger.warning("Radio connection lost, broadcasting status change")
+                        broadcast_health(False, self._port)
+                        self._last_connected = False
 
-                    # Attempt reconnection
-                    await asyncio.sleep(3)  # Wait a bit before trying
-                    await self.reconnect()
+                        # Attempt reconnection
+                        await asyncio.sleep(3)  # Wait a bit before trying
+                        if await self.reconnect():
+                            # Re-register event handlers after successful reconnect
+                            from app.event_handlers import register_event_handlers
+                            if self._meshcore:
+                                register_event_handlers(self._meshcore)
+                                await self._meshcore.start_auto_message_fetching()
+                                logger.info("Event handlers re-registered after auto-reconnect")
 
-                elif not self._last_connected and current_connected:
-                    # Connection restored (might have reconnected automatically)
-                    logger.info("Radio connection restored")
-                    broadcast_health(True, self._port)
-                    self._last_connected = True
+                    elif not self._last_connected and current_connected:
+                        # Connection restored (might have reconnected automatically)
+                        logger.info("Radio connection restored")
+                        broadcast_health(True, self._port)
+                        self._last_connected = True
+
+                except asyncio.CancelledError:
+                    # Task is being cancelled, exit cleanly
+                    break
+                except Exception as e:
+                    # Log error but continue monitoring - don't let the monitor die
+                    logger.exception("Error in connection monitor, continuing: %s", e)
 
         self._reconnect_task = asyncio.create_task(monitor_loop())
         logger.info("Radio connection monitor started")
diff --git a/app/radio_sync.py b/app/radio_sync.py
index 91e180cf..c8a45251 100644
--- a/app/radio_sync.py
+++ b/app/radio_sync.py
@@ -29,19 +29,27 @@ _message_poll_task: asyncio.Task | None = None
 # Message poll interval in seconds
 MESSAGE_POLL_INTERVAL = 5
 
-# Flag to pause polling during repeater operations
-_polling_paused: bool = False
+# Counter to pause polling during repeater operations (supports nested pauses)
+_polling_pause_count: int = 0
+
+
+def is_polling_paused() -> bool:
+    """Check if polling is currently paused."""
+    return _polling_pause_count > 0
 
 
 @asynccontextmanager
 async def pause_polling():
-    """Context manager to pause message polling during repeater operations."""
-    global _polling_paused
-    _polling_paused = True
+    """Context manager to pause message polling during repeater operations.
+
+    Supports nested pauses - polling only resumes when all pause contexts have exited.
+    """
+    global _polling_pause_count
+    _polling_pause_count += 1
     try:
         yield
     finally:
-        _polling_paused = False
+        _polling_pause_count -= 1
 
 # Background task handle
 _sync_task: asyncio.Task | None = None
@@ -291,7 +299,7 @@ async def _message_poll_loop():
         try:
             await asyncio.sleep(MESSAGE_POLL_INTERVAL)
 
-            if radio_manager.is_connected and not _polling_paused:
+            if radio_manager.is_connected and not is_polling_paused():
                 await poll_for_messages()
 
         except asyncio.CancelledError:
diff --git a/tests/test_radio_sync.py b/tests/test_radio_sync.py
new file mode 100644
index 00000000..9a6cc2e5
--- /dev/null
+++ b/tests/test_radio_sync.py
@@ -0,0 +1,115 @@
+"""Tests for radio_sync module.
+
+These tests verify the polling pause mechanism that prevents
+message polling from interfering with repeater CLI operations.
+"""
+
+import pytest
+
+from app.radio_sync import (
+    _polling_pause_count,
+    is_polling_paused,
+    pause_polling,
+)
+
+
+@pytest.fixture(autouse=True)
+def reset_polling_state():
+    """Reset polling pause state before and after each test."""
+    import app.radio_sync as radio_sync
+    radio_sync._polling_pause_count = 0
+    yield
+    radio_sync._polling_pause_count = 0
+
+
+class TestPollingPause:
+    """Test the polling pause mechanism."""
+
+    def test_initially_not_paused(self):
+        """Polling is not paused by default."""
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_pause_polling_pauses(self):
+        """pause_polling context manager pauses polling."""
+        assert not is_polling_paused()
+
+        async with pause_polling():
+            assert is_polling_paused()
+
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_nested_pause_stays_paused(self):
+        """Nested pause_polling contexts keep polling paused until all exit."""
+        assert not is_polling_paused()
+
+        async with pause_polling():
+            assert is_polling_paused()
+
+            async with pause_polling():
+                assert is_polling_paused()
+
+            # Still paused - outer context active
+            assert is_polling_paused()
+
+        # Now unpaused - all contexts exited
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_triple_nested_pause(self):
+        """Three levels of nesting work correctly."""
+        async with pause_polling():
+            async with pause_polling():
+                async with pause_polling():
+                    assert is_polling_paused()
+                assert is_polling_paused()
+            assert is_polling_paused()
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_pause_resumes_on_exception(self):
+        """Polling resumes even if exception occurs in context."""
+        try:
+            async with pause_polling():
+                assert is_polling_paused()
+                raise ValueError("Test error")
+        except ValueError:
+            pass
+
+        # Should be unpaused despite exception
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_nested_pause_resumes_correctly_on_inner_exception(self):
+        """Nested contexts handle exceptions correctly."""
+        async with pause_polling():
+            try:
+                async with pause_polling():
+                    assert is_polling_paused()
+                    raise ValueError("Inner error")
+            except ValueError:
+                pass
+
+            # Outer context still active
+            assert is_polling_paused()
+
+        # All contexts exited
+        assert not is_polling_paused()
+
+    @pytest.mark.asyncio
+    async def test_counter_increments_and_decrements(self):
+        """Counter correctly tracks pause depth."""
+        import app.radio_sync as radio_sync
+
+        assert radio_sync._polling_pause_count == 0
+
+        async with pause_polling():
+            assert radio_sync._polling_pause_count == 1
+
+            async with pause_polling():
+                assert radio_sync._polling_pause_count == 2
+
+            assert radio_sync._polling_pause_count == 1
+
+        assert radio_sync._polling_pause_count == 0