diff --git a/logtail/handler.py b/logtail/handler.py
index 0349e2d..a7bb78b 100644
--- a/logtail/handler.py
+++ b/logtail/handler.py
@@ -95,9 +95,16 @@ def emit(self, record):
                 raise e
 
     def flush(self):
-        if self.flush_thread and self.flush_thread.is_alive():
-            if not self.flush_thread.flush(timeout=self.flush_timeout):
-                print('Gave up waiting for Better Stack uploads after {}s, logs are still buffered'.format(self.flush_timeout))
+        if not (self.flush_thread and self.flush_thread.is_alive()):
+            return
+        if logging._lock._is_owned():
+            # logging.config.dictConfig() flushes the handlers it replaces while holding the global
+            # logging lock, and the worker's upload needs that lock whenever urllib3's logger has a
+            # level-cache miss, so waiting here could only deadlock. Nothing is lost: the worker
+            # keeps running and sends what is queued as soon as the lock is released.
+            return
+        if not self.flush_thread.flush(timeout=self.flush_timeout):
+            print('Gave up waiting for Better Stack uploads after {}s, logs are still buffered'.format(self.flush_timeout))
 
     def _reset_after_fork(self):
         # A forked child inherits the parent's queue with whatever was still buffered in it,
diff --git a/tests/test_handler.py b/tests/test_handler.py
index d447eb9..2c7f87f 100644
--- a/tests/test_handler.py
+++ b/tests/test_handler.py
@@ -411,6 +411,35 @@ def upload(frame):
         self.assertEqual(uploads, [['hello']])
         self.assertTrue(handler.pipe.empty())
 
+    def test_flush_does_not_wait_while_the_caller_holds_the_logging_lock(self):
+        # logging.config.dictConfig() flushes the handlers it replaces while holding the global
+        # logging lock, and the worker's upload needs that lock whenever urllib3's logger has a
+        # level-cache miss, so waiting for the worker there can only deadlock.
+        logger = logging.getLogger(__name__)
+        logger.handlers = []
+        logger.setLevel(logging.INFO)
+        handler = LogtailHandler(source_token=self.source_token, flush_interval=0.01, check_interval=0.01, flush_timeout=2)
+        uploads = []
+        in_upload = threading.Event()
+
+        def upload(frame):
+            in_upload.set()
+            with logging._lock:  # what urllib3's isEnabledFor() does on a level-cache miss
+                uploads.append([f['message'] for f in frame])
+            return mock.MagicMock(status_code=202)
+
+        handler.uploader = upload
+        logger.addHandler(handler)
+        self.addCleanup(self._stop_flush_worker, handler)
+
+        with logging._lock:
+            logger.info('hello')
+            self.assertTrue(in_upload.wait(2))
+            started = time.time()
+            handler.flush()
+            self.assertLess(time.time() - started, 0.5, 'flush() waited for a worker that needs the lock we hold')
+        self._wait_until(lambda: uploads == [['hello']])
+
     def _wait_until(self, condition):
         deadline = time.time() + 2
         while not condition() and time.time() < deadline: