diff --git a/src/ad_test/test_file_change.py b/src/ad_test/test_file_change.py
index b7139d5..7dde753 100644
--- a/src/ad_test/test_file_change.py
+++ b/src/ad_test/test_file_change.py
@@ -1,5 +1,6 @@
 import asyncio
 import logging
+import random
 import re
 from pathlib import Path
 
@@ -24,6 +25,13 @@ def modify_file(path: Path):
     path.write_text(modified_content)
 
 
+def insert_importerror(path: Path):
+    file_content = path.read_text().splitlines()
+    # i = random.randint(0, len(file_content))
+    file_content.insert(0, 'raise ImportError')
+    path.write_text('\n'.join(file_content))
+
+
 def test_file(ad: AppDaemon, caplog: pytest.LogCaptureFixture, config_repo: Repo):
     assert isinstance(ad, AppDaemon)
 
@@ -39,3 +47,23 @@ def test_file(ad: AppDaemon, caplog: pytest.LogCaptureFixture, config_repo: Repo
 
         reset_file(config_repo, module_file)
         ad.loop.run_until_complete(asyncio.sleep(1.0))
+
+
+def test_file_with_error(ad: AppDaemon, caplog: pytest.LogCaptureFixture, config_repo: Repo):
+    assert isinstance(ad, AppDaemon)
+
+    module_file = Path(food.meal.__file__)
+    insert_importerror(module_file)
+
+    try:
+        with caplog.at_level(logging.DEBUG, logger='AppDaemon._app_management'):
+            ad.loop.run_until_complete(asyncio.sleep(1.0))
+
+            module_load_order = get_load_order(caplog)
+            assert module_load_order == ['food.meal', 'restaurant']
+
+            reset_file(config_repo, module_file)
+            ad.loop.run_until_complete(asyncio.sleep(1.0))
+            assert "Started 'my_restaurant'" in caplog.text
+    finally:
+        reset_file(config_repo, module_file)