diff --git a/homeassistant/bootstrap.py b/homeassistant/bootstrap.py
index f1136123999..66312f7283a 100644
--- a/homeassistant/bootstrap.py
+++ b/homeassistant/bootstrap.py
@@ -342,7 +342,11 @@ def async_enable_logging(
                 err_log_path, backupCount=1
             )
 
-        err_handler.doRollover()
+        try:
+            err_handler.doRollover()
+        except OSError as err:
+            _LOGGER.error("Error rolling over log file: %s", err)
+
         err_handler.setLevel(logging.INFO if verbose else logging.WARNING)
         err_handler.setFormatter(logging.Formatter(fmt, datefmt=datefmt))
 
diff --git a/tests/test_bootstrap.py b/tests/test_bootstrap.py
index 929cbbf6e81..3eeb06d056c 100644
--- a/tests/test_bootstrap.py
+++ b/tests/test_bootstrap.py
@@ -56,11 +56,14 @@ async def test_home_assistant_core_config_validation(hass):
     assert result is None
 
 
-async def test_async_enable_logging(hass):
+async def test_async_enable_logging(hass, caplog):
     """Test to ensure logging is migrated to the queue handlers."""
     with patch("logging.getLogger"), patch(
         "homeassistant.bootstrap.async_activate_log_queue_handler"
-    ) as mock_async_activate_log_queue_handler:
+    ) as mock_async_activate_log_queue_handler, patch(
+        "homeassistant.bootstrap.logging.handlers.RotatingFileHandler.doRollover",
+        side_effect=OSError,
+    ):
         bootstrap.async_enable_logging(hass)
         mock_async_activate_log_queue_handler.assert_called_once()
         mock_async_activate_log_queue_handler.reset_mock()
@@ -75,6 +78,8 @@ async def test_async_enable_logging(hass):
         for f in glob.glob("testing_config/home-assistant.log*"):
             os.remove(f)
 
+    assert "Error rolling over log file" in caplog.text
+
 
 async def test_load_hassio(hass):
     """Test that we load Hass.io component."""