diff --git a/modules/plex.py b/modules/plex.py
index 6a375740..9ae4c7dc 100644
--- a/modules/plex.py
+++ b/modules/plex.py
@@ -770,7 +770,7 @@ class Plex:
 
     def update_item_from_assets(self, item, overlay=None):
         name = os.path.basename(os.path.dirname(item.locations[0]) if self.is_movie else item.locations[0])
-        found_one = False
+        found_folder = False
         uploaded = False
         for ad in self.asset_directory:
             poster = None
@@ -785,20 +785,21 @@ class Plex:
                         item_dir = os.path.abspath(matches[0])
                 if item_dir is None:
                     continue
-                found_one = True
+                found_folder = True
                 poster_filter = os.path.join(item_dir, "poster.*")
                 background_filter = os.path.join(item_dir, "background.*")
             else:
                 poster_filter = os.path.join(ad, f"{name}.*")
                 background_filter = os.path.join(ad, f"{name}_background.*")
+            logger.debug(f"Poster Filter: {poster_filter}")
             matches = glob.glob(poster_filter)
             if len(matches) > 0:
                 poster = ImageData("asset_directory", os.path.abspath(matches[0]), prefix=f"{item.title}'s ", is_url=False)
+            logger.debug(f"Background Filter: {background_filter}")
             matches = glob.glob(background_filter)
             if len(matches) > 0:
                 background = ImageData("asset_directory", os.path.abspath(matches[0]), prefix=f"{item.title}'s ", is_poster=False, is_url=False)
             if poster or background:
-                uploaded = True
                 self.upload_images(item, poster=poster, background=background, overlay=overlay)
             if self.is_show:
                 for season in self.query(item.seasons):
@@ -819,12 +820,12 @@ class Plex:
                         if len(matches) > 0:
                             episode_poster = ImageData("asset_directory", os.path.abspath(matches[0]), prefix=f"{item.title} {episode.seasonEpisode.upper()}'s ", is_url=False)
                             self.upload_images(episode, poster=episode_poster)
-        if not found_one and overlay:
+        if not found_folder and overlay:
             self.upload_images(item, overlay=overlay)
-        elif not found_one:
+        elif self.asset_folders and not found_folder:
             logger.error(f"Asset Warning: No asset folder found called '{name}'")
-        elif not uploaded:
-            logger.error(f"Asset Warning: No poster or background found in an assets folder")
+        elif not poster and not background:
+            logger.error(f"Asset Warning: No poster or background found in an assets folder for {name}")
 
     def find_collection_assets(self, item, name=None):
         if name is None: