diff --git a/modules/library.py b/modules/library.py
index d21f5430..b8565cd7 100644
--- a/modules/library.py
+++ b/modules/library.py
@@ -275,7 +275,7 @@ class Library(ABC):
             exif_tags = image.getexif()
         if 0x04bc in exif_tags and exif_tags[0x04bc] == "overlay":
             os.remove(image_path)
-            raise Failed("Poster already has an Overlay")
+            raise Failed("This item's poster already has an Overlay. There is no PMM setting to change; manual attention required.")
         if remove:
             os.remove(image_path)
         else:
diff --git a/modules/mdblist.py b/modules/mdblist.py
index 99154574..10a43481 100644
--- a/modules/mdblist.py
+++ b/modules/mdblist.py
@@ -205,6 +205,6 @@ class Mdblist:
                         results.append((item["id"], "tmdb" if item["mediatype"] == "movie" else "tmdb_show"))
                 return results
             except JSONDecodeError:
-                raise Failed(f"Mdblist Error: Invalid Response")
+                raise Failed(f"Mdblist Error: Invalid JSON Response received")
         else:
             raise Failed(f"Mdblist Error: Method {method} not supported")
diff --git a/modules/notifiarr.py b/modules/notifiarr.py
index a58c55a6..52bd8f05 100644
--- a/modules/notifiarr.py
+++ b/modules/notifiarr.py
@@ -17,7 +17,7 @@ class Notifiarr:
         try:
             self.request(path="user", params={"fetch": "settings"})
         except JSONDecodeError:
-            raise Failed("Notifiarr Error: Invalid response")
+            raise Failed("Notifiarr Error: Invalid JSON response received")
 
     def notification(self, json):
         return self.request(json=json)
diff --git a/modules/overlay.py b/modules/overlay.py
index e79f7ba1..4c5b323a 100644
--- a/modules/overlay.py
+++ b/modules/overlay.py
@@ -155,8 +155,10 @@ class Overlay:
 
         def get_and_save_image(image_url):
             response = self.config.get(image_url)
-            if response.status_code >= 400:
+            if response.status_code == 404:
                 raise Failed(f"Overlay Error: Overlay Image not found at: {image_url}")
+            if response.status_code >= 400:
+                raise Failed(f"Overlay Error: Status {response.status_code} when attempting download of: {image_url}")
             if "Content-Type" not in response.headers or response.headers["Content-Type"] != "image/png":
                 raise Failed(f"Overlay Error: Overlay Image not a png: {image_url}")
             if not os.path.exists(library.overlay_folder) or not os.path.isdir(library.overlay_folder):
diff --git a/modules/plex.py b/modules/plex.py
index d0e0ae70..12ef28a8 100644
--- a/modules/plex.py
+++ b/modules/plex.py
@@ -1358,7 +1358,7 @@ class Plex(Library):
                 else:
                     starting = item
                 if not starting.locations:
-                    raise Failed(f"Asset Warning: No video filepath found fo {item.title}")
+                    raise Failed(f"Asset Warning: No video filepath found for {item.title}")
                 path_test = str(starting.locations[0])
                 if not os.path.dirname(path_test):
                     path_test = path_test.replace("\\", "/")
diff --git a/modules/util.py b/modules/util.py
index d402d4c5..eb620c34 100644
--- a/modules/util.py
+++ b/modules/util.py
@@ -170,8 +170,10 @@ def quote(data):
 
 def download_image(title, image_url, download_directory, filename=None):
     response = requests.get(image_url, headers=header())
+    if response.status_code == 404:
+        raise Failed(f"Image Error: Not Found on Image URL: {image_url}")
     if response.status_code >= 400:
-        raise Failed(f"Image Error: Failed to download Image URL: {image_url}")
+        raise Failed(f"Image Error: {response.status_code} on Image URL: {image_url}")
     if "Content-Type" not in response.headers or response.headers["Content-Type"] not in image_content_types:
         raise Failed("Image Not PNG, JPG, or WEBP")
     new_image = os.path.join(download_directory, f"{filename}") if filename else download_directory