diff --git a/homeassistant/bootstrap.py b/homeassistant/bootstrap.py
index 9e375c7fdb8..96af205e4e0 100644
--- a/homeassistant/bootstrap.py
+++ b/homeassistant/bootstrap.py
@@ -624,13 +624,16 @@ async def async_enable_logging(
 
     if log_file is None:
         default_log_path = hass.config.path(ERROR_LOG_FILENAME)
-        if "SUPERVISOR" in os.environ:
-            _LOGGER.info("Running in Supervisor, not logging to file")
+        if "SUPERVISOR" in os.environ and "HA_DUPLICATE_LOG_FILE" not in os.environ:
             # Rename the default log file if it exists, since previous versions created
             # it even on Supervisor
-            if os.path.isfile(default_log_path):
-                with contextlib.suppress(OSError):
-                    os.rename(default_log_path, f"{default_log_path}.old")
+            def rename_old_file() -> None:
+                """Rename old log file in executor."""
+                if os.path.isfile(default_log_path):
+                    with contextlib.suppress(OSError):
+                        os.rename(default_log_path, f"{default_log_path}.old")
+
+            await hass.async_add_executor_job(rename_old_file)
             err_log_path = None
         else:
             err_log_path = default_log_path
diff --git a/tests/test_bootstrap.py b/tests/test_bootstrap.py
index 8f6a59a2915..e3d32354e49 100644
--- a/tests/test_bootstrap.py
+++ b/tests/test_bootstrap.py
@@ -130,8 +130,16 @@ async def test_async_enable_logging(
     cleanup_log_files()
 
 
+@pytest.mark.parametrize(
+    ("extra_env", "log_file_count", "old_log_file_count"),
+    [({}, 0, 1), ({"HA_DUPLICATE_LOG_FILE": "1"}, 1, 0)],
+)
 async def test_async_enable_logging_supervisor(
-    hass: HomeAssistant, caplog: pytest.LogCaptureFixture
+    hass: HomeAssistant,
+    caplog: pytest.LogCaptureFixture,
+    extra_env: dict[str, str],
+    log_file_count: int,
+    old_log_file_count: int,
 ) -> None:
     """Test to ensure the default log file is not created on Supervisor installations."""
 
@@ -141,14 +149,14 @@ async def test_async_enable_logging_supervisor(
     assert len(glob.glob(ARG_LOG_FILE)) == 0
 
     with (
-        patch.dict(os.environ, {"SUPERVISOR": "1"}),
+        patch.dict(os.environ, {"SUPERVISOR": "1", **extra_env}),
         patch(
             "homeassistant.bootstrap.async_activate_log_queue_handler"
         ) as mock_async_activate_log_queue_handler,
         patch("logging.getLogger"),
     ):
         await bootstrap.async_enable_logging(hass)
-        assert len(glob.glob(CONFIG_LOG_FILE)) == 0
+        assert len(glob.glob(CONFIG_LOG_FILE)) == log_file_count
         mock_async_activate_log_queue_handler.assert_called_once()
         mock_async_activate_log_queue_handler.reset_mock()
 
@@ -162,9 +170,10 @@ async def test_async_enable_logging_supervisor(
         await hass.async_add_executor_job(write_log_file)
         assert len(glob.glob(CONFIG_LOG_FILE)) == 1
         assert len(glob.glob(f"{CONFIG_LOG_FILE}.old")) == 0
+
         await bootstrap.async_enable_logging(hass)
-        assert len(glob.glob(CONFIG_LOG_FILE)) == 0
-        assert len(glob.glob(f"{CONFIG_LOG_FILE}.old")) == 1
+        assert len(glob.glob(CONFIG_LOG_FILE)) == log_file_count
+        assert len(glob.glob(f"{CONFIG_LOG_FILE}.old")) == old_log_file_count
         mock_async_activate_log_queue_handler.assert_called_once()
         mock_async_activate_log_queue_handler.reset_mock()