diff --git a/src_py/hat/syslog/handler.py b/src_py/hat/syslog/handler.py
index 098c148..ff6e7a6 100644
--- a/src_py/hat/syslog/handler.py
+++ b/src_py/hat/syslog/handler.py
@@ -151,6 +151,7 @@ def _logging_handler_thread(state):
             time.sleep(state.reconnect_delay)
             continue
 
+        msg = None
         try:
             while True:
                 with state.cv:
@@ -161,23 +162,24 @@ def _logging_handler_thread(state):
                         return
 
                     if state.dropped[0]:
-                        msg = _create_dropped_msg(
+                        msg = None
+                        dropped_msg = _create_dropped_msg(
                             state.dropped[0], '_logging_handler_thread', 0)
+                        _send_message(s, dropped_msg, state.comm_type == common.CommType.UDP)
                         state.dropped[0] = 0
+                        continue
 
                     else:
                         msg = state.queue.popleft()
 
-                msg_bytes = encoder.msg_to_str(msg).encode()
-
-                if state.comm_type == common.CommType.UDP:
-                    s.send(msg_bytes)
-
-                else:
-                    s.send(f'{len(msg_bytes)} '.encode() + msg_bytes)
+                _send_message(s, msg, state.comm_type == common.CommType.UDP)
+                msg = None
 
         except Exception:
-            pass
+            # When failing with msg assigned, put the msg back.
+            # After reconnecting we will try it again.
+            if msg is not None:
+                state.queue.appendleft(msg)
 
         finally:
             with contextlib.suppress(Exception):
@@ -212,6 +214,14 @@ def _record_to_msg(record):
         msg=record.getMessage())
 
 
+def _send_message(s, msg, only_bytes=False):
+    msg_bytes = encoder.msg_to_str(msg).encode()
+    if only_bytes:
+        s.send(msg_bytes)
+    else:
+        s.send(f'{len(msg_bytes)} '.encode() + msg_bytes)
+
+
 def _create_dropped_msg(dropped, func_name, lineno):
     hat_data = {'name': __name__,
                 'thread': str(threading.get_ident()),