diff --git a/jarvis/cogs/image.py b/jarvis/cogs/image.py
index daac58b..da8a1c3 100644
--- a/jarvis/cogs/image.py
+++ b/jarvis/cogs/image.py
@@ -56,7 +56,7 @@ class ImageCog(commands.Cog):
             await ctx.send("Image already meets target.")
             return
 
-        ratio = tgt_size / size
+        ratio = tgt_size / size - 0.05
 
         # TODO: Optimize to not run multiple times
         while len(file) > tgt_size:
@@ -69,6 +69,7 @@ class ImageCog(commands.Cog):
 
             new_img = cv2.resize(img, (width, height))
             file = cv2.imencode(".png", new_img)[1].tobytes()
+            ratio = tgt_size / len(file) - 0.05
 
         bufio = BytesIO(file)
         await ctx.send(