diff --git a/CHANGELOG b/CHANGELOG
index 6f7a9eaf..c515f3e1 100644
--- a/CHANGELOG
+++ b/CHANGELOG
@@ -25,6 +25,7 @@ Add `trakt`, `omdb_metascore`, `omdb_tomatoes` ratings sources for mass operatio
 Add `trakt` ratings source for mass episode operations.
 Added GitHub token validation during config validation.
 add `plex` ratings source for mass operations.
+Orderly error and no caching on too-large image
 
 # Docs
 Added "getting started" page
diff --git a/VERSION b/VERSION
index dd2a72f7..7b2d944d 100644
--- a/VERSION
+++ b/VERSION
@@ -1 +1 @@
-2.1.0-build53
+2.1.0-build54
diff --git a/modules/library.py b/modules/library.py
index 6e86ee51..96f65f09 100644
--- a/modules/library.py
+++ b/modules/library.py
@@ -212,8 +212,7 @@ class Library(ABC):
                         self.reload(item, force=True)
                         if overlay and "Overlay" in [la.tag for la in self.item_labels(item)]:
                             item.removeLabel("Overlay")
-                    self._upload_image(item, poster)
-                    poster_uploaded = True
+                    poster_uploaded = self._upload_image(item, poster)
                     logger.info(f"Metadata: {poster.attribute} updated {poster.message}")
                 elif self.show_asset_not_needed:
                     logger.info(f"Metadata: {poster.prefix}poster update not needed")
@@ -228,8 +227,7 @@ class Library(ABC):
                 if self.config.Cache:
                     _, image_compare, _ = self.config.Cache.query_image_map(item.ratingKey, f"{self.image_table_name}_backgrounds")
                 if not image_compare or str(background.compare) != str(image_compare):
-                    self._upload_image(item, background)
-                    background_uploaded = True
+                    background_uploaded = self._upload_image(item, background)
                     logger.info(f"Metadata: {background.attribute} updated {background.message}")
                 elif self.show_asset_not_needed:
                     logger.info(f"Metadata: {background.prefix}background update not needed")
diff --git a/modules/plex.py b/modules/plex.py
index b0978f20..adbc687a 100644
--- a/modules/plex.py
+++ b/modules/plex.py
@@ -442,6 +442,8 @@ watchlist_sorts = {
     "critic_rating.asc": "rating:asc", "critic_rating.desc": "rating:desc",
 }
 
+MAX_IMAGE_SIZE = 10480000  # a little less than 10MB
+
 class Plex(Library):
     def __init__(self, config, params):
         super().__init__(config, params)
@@ -766,6 +768,13 @@ class Plex(Library):
                 item_list.append(item)
         return item_list
 
+    def validate_image_size(self, image):
+        if image.compare < MAX_IMAGE_SIZE:
+            return True
+        else:
+            logger.error(f"Image too large: {image.location}, bytes {image.compare}, MAX {MAX_IMAGE_SIZE}")
+            return False
+
     @retry(stop=stop_after_attempt(6), wait=wait_fixed(10), retry=retry_if_not_exception_type((BadRequest, NotFound, Unauthorized)))
     def reload(self, item, force=False):
         is_full = False
@@ -789,6 +798,7 @@ class Plex(Library):
 
     @retry(stop=stop_after_attempt(6), wait=wait_fixed(10), retry=retry_if_not_exception_type((BadRequest, NotFound, Unauthorized)))
     def _upload_image(self, item, image):
+        upload_success = True
         try:
             if image.is_url and "theposterdb.com" in image.location:
                 now = datetime.now()
@@ -800,12 +810,17 @@ class Plex(Library):
             if image.is_poster and image.is_url:
                 item.uploadPoster(url=image.location)
             elif image.is_poster:
-                item.uploadPoster(filepath=image.location)
+                upload_success = self.validate_image_size(image)
+                if upload_success:
+                    item.uploadPoster(filepath=image.location)
             elif image.is_url:
                 item.uploadArt(url=image.location)
             else:
-                item.uploadArt(filepath=image.location)
+                upload_success = self.validate_image_size(image)
+                if upload_success:
+                    item.uploadArt(filepath=image.location)
             self.reload(item, force=True)
+            return upload_success
         except BadRequest as e:
             item.refresh()
             raise Failed(e)