diff --git a/src/ytdl_sub/downloaders/youtube/channel.py b/src/ytdl_sub/downloaders/youtube/channel.py
index c697f78c..4a369cc8 100644
--- a/src/ytdl_sub/downloaders/youtube/channel.py
+++ b/src/ytdl_sub/downloaders/youtube/channel.py
@@ -228,7 +228,7 @@ class YoutubeChannelDownloader(YoutubeDownloader[YoutubeChannelDownloaderOptions
         self,
         thumbnail_url: str,
         output_thumbnail_path: str,
-    ):
+    ) -> Optional[bool]:
         """
         Downloads a thumbnail and stores it in the output directory
 
@@ -238,12 +238,16 @@ class YoutubeChannelDownloader(YoutubeDownloader[YoutubeChannelDownloaderOptions
             Url of the thumbnail
         output_thumbnail_path:
             Path to store the thumbnail after downloading
+
+        Returns
+        -------
+        True if the thumbnail converted. None if it is missing or failed.
         """
         if not thumbnail_url:
             download_logger.warning("Could not find a thumbnail for %s", self.channel.uid)
-            return
+            return None
 
-        convert_url_thumbnail(
+        return convert_url_thumbnail(
             thumbnail_url=thumbnail_url, output_thumbnail_path=output_thumbnail_path
         )
 
diff --git a/src/ytdl_sub/utils/thumbnail.py b/src/ytdl_sub/utils/thumbnail.py
index 4e5aaabb..834203c8 100644
--- a/src/ytdl_sub/utils/thumbnail.py
+++ b/src/ytdl_sub/utils/thumbnail.py
@@ -1,4 +1,5 @@
 import tempfile
+from typing import Optional
 from urllib.request import urlopen
 
 from ytdl_sub.entries.entry import Entry
@@ -34,7 +35,7 @@ def convert_download_thumbnail(entry: Entry, error_if_not_found: bool = True) ->
 
 
 @retry(times=5, exceptions=(Exception,))
-def convert_url_thumbnail(thumbnail_url: str, output_thumbnail_path: str) -> bool:
+def convert_url_thumbnail(thumbnail_url: str, output_thumbnail_path: str) -> Optional[bool]:
     """
     Downloads and converts a thumbnail from a url into a jpg
 
@@ -47,7 +48,7 @@ def convert_url_thumbnail(thumbnail_url: str, output_thumbnail_path: str) -> boo
 
     Returns
     -------
-    True to indicate it converted the thumbnail from url
+    True to indicate it converted the thumbnail from url. None if the retry failed.
     """
     with urlopen(thumbnail_url) as file:
         with tempfile.NamedTemporaryFile() as thumbnail:
diff --git a/tests/e2e/youtube/test_channel.py b/tests/e2e/youtube/test_channel.py
index f6b21a4a..1b43a53f 100644
--- a/tests/e2e/youtube/test_channel.py
+++ b/tests/e2e/youtube/test_channel.py
@@ -70,12 +70,13 @@ class TestChannelAsKodiTvShow:
             config=channel_as_tv_show_config, preset_name="pz", preset_dict=channel_preset_dict
         )
 
-        with assert_debug_log(
+        with assert_debug_log(  # Ensure retry debug message is thrown
             logger=retry_logger,
-            expected_message="Exception thrown when attempting to run convert_url_thumbnail, attempt 5 of 5",
-        ), patch("ytdl_sub.utils.retry.sleep"), patch(
+            expected_message="Exception thrown when attempting to run %s, attempt %d of %d",
+        ), patch(  # Make sleeps instant
+            "ytdl_sub.utils.retry.sleep"
+        ), patch(  # Mock error when calling urlopen
             "ytdl_sub.utils.thumbnail.urlopen"
         ) as mock_urlopen:
             mock_urlopen.side_effect = [Exception("error")]
-
             full_channel_subscription.download(dry_run=True)