diff --git a/jarvis/cogs/image.py b/jarvis/cogs/image.py
index a37c8b8..e25f60c 100644
--- a/jarvis/cogs/image.py
+++ b/jarvis/cogs/image.py
@@ -69,7 +69,9 @@ class ImageCog(commands.Cog):
 
         accuracy = 0.0
         # TODO: Optimize to not run multiple times
-        while len(file) > tgt_size or accuracy < 0.50:
+        while len(file) > tgt_size or (
+            len(file) < tgt_size and accuracy < 0.50
+        ):
             old_file = file
 
             buffer = np.frombuffer(file, dtype=np.uint8)