diff --git a/tests/definitions_test.py b/tests/definitions_test.py
index 85701d8af..78e479021 100644
--- a/tests/definitions_test.py
+++ b/tests/definitions_test.py
@@ -221,7 +221,7 @@ def test_definitions(file_path, schema, change_type):
     # Check for images if front_image or rear_image is True
     if (definition.get('front_image') or definition.get('rear_image')):
         # Find images for given manufacturer, with matching device slug (exact match including case)
-        manufacturer_images = [image[1] for image in image_files if image[0] == file_path.split('/')[1] and os.path.basename(image[1]).split('.')[0] == this_device.get_slug()]
+        manufacturer_images = [image[1] for image in image_files if image[0] == file_path.split(os.path.sep)[1] and os.path.basename(image[1]).split('.')[0] == this_device.get_slug()]
         if not manufacturer_images:
             pytest.fail(f'{file_path} has Front or Rear Image set to True but no images found for manufacturer/device (slug={this_device.get_slug()})', False)
         elif len(manufacturer_images)>2:
@@ -232,13 +232,12 @@ def test_definitions(file_path, schema, change_type):
             front_image = [image_path.split('/')[2] for image_path in manufacturer_images if os.path.basename(image_path).split('.')[1] == 'front']
 
             if not front_image:
-                pytest.fail(f'{file_path} has front_image set to True but no matching image found for device ({manufacturer_images})', False)
+                pytest.fail(f'{file_path} has front_image set to True but no matching image found (looking for \'elevation-images{os.path.sep}{file_path.split(os.path.sep)[1]}{os.path.sep}{this_device.get_slug()}.front.ext\' but only found {manufacturer_images})', False)
 
-        # If rear_image is True, verify that a front image exists
+        # If rear_image is True, verify that a rear image exists
         if(definition.get('rear_image')):
             rear_image = [image_path.split('/')[2] for image_path in manufacturer_images if os.path.basename(image_path).split('.')[1] == 'rear']
 
             if not rear_image:
-                pytest.fail(f'{file_path} has rear_image set to True but no images found for device', False)
-
+                pytest.fail(f'{file_path} has rear_image set to True but no matching image found (looking for \'elevation-images{os.path.sep}{file_path.split(os.path.sep)[1]}{os.path.sep}{this_device.get_slug()}.rear.ext\' but only found {manufacturer_images})', False)
     iterdict(definition)