diff --git a/jarvis/cogs/image.py b/jarvis/cogs/image.py
index 7328921..d711b5b 100644
--- a/jarvis/cogs/image.py
+++ b/jarvis/cogs/image.py
@@ -58,15 +58,19 @@ class ImageCog(commands.Cog):
 
         ratio = tgt_size / size
 
-        buffer = np.frombuffer(file, dtype=np.uint8)
-        img = cv2.imdecode(buffer, flags=-1)
+        # TODO: Optimize to not run multiple times
+        while len(file) > tgt_size:
 
-        width = int(img.shape[1] * ratio)
-        height = int(img.shape[0] * ratio)
+            buffer = np.frombuffer(file, dtype=np.uint8)
+            img = cv2.imdecode(buffer, flags=-1)
 
-        new_img = cv2.resize(img, (width, height))
-        buffer = cv2.imencode(".png", new_img)[1].tobytes()
-        bufio = BytesIO(buffer)
+            width = int(img.shape[1] * ratio)
+            height = int(img.shape[0] * ratio)
+
+            new_img = cv2.resize(img, (width, height))
+            file = cv2.imencode(".png", new_img)[1].tobytes()
+
+        bufio = BytesIO(file)
         await ctx.send(file=File(bufio, filename="resized.png"))