diff --git a/jarvis/cogs/image.py b/jarvis/cogs/image.py
index 54cdad2..ec4a459 100644
--- a/jarvis/cogs/image.py
+++ b/jarvis/cogs/image.py
@@ -67,8 +67,10 @@ class ImageCog(commands.Cog):
 
         ratio = tgt_size / size - 0.02
 
+        accuracy = 0.0
         # TODO: Optimize to not run multiple times
         while len(file) > tgt_size:
+            old_file = file
 
             buffer = np.frombuffer(file, dtype=np.uint8)
             img = cv2.imdecode(buffer, flags=-1)
@@ -78,7 +80,12 @@ class ImageCog(commands.Cog):
 
             new_img = cv2.resize(img, (width, height))
             file = cv2.imencode(".png", new_img)[1].tobytes()
-            ratio = tgt_size / len(file) - 0.02
+            accuracy = (len(file) / tgt_size) * 100
+            if accuracy <= 0.50:
+                file = old_file
+                ratio = ratio + 0.1
+            else:
+                ratio = tgt_size / len(file) - 0.02
 
         bufio = BytesIO(file)
         accuracy = (len(file) / tgt_size) * 100