diff --git a/cogs/draw_image_generation.py b/cogs/draw_image_generation.py
index bb7fb11..7cc80a5 100644
--- a/cogs/draw_image_generation.py
+++ b/cogs/draw_image_generation.py
@@ -47,7 +47,7 @@ class DrawDallEService(discord.Cog, name="DrawDallEService"):
 
         try:
             file, image_urls = await self.model.send_image_request(
-                prompt, vary=vary if not draw_from_optimizer else None
+                ctx, prompt, vary=vary if not draw_from_optimizer else None
             )
         except ValueError as e:
             (
diff --git a/cogs/image_prompt_optimizer.py b/cogs/image_prompt_optimizer.py
index 281b663..c136e71 100644
--- a/cogs/image_prompt_optimizer.py
+++ b/cogs/image_prompt_optimizer.py
@@ -183,7 +183,7 @@ class DrawButton(discord.ui.Button["OptimizeView"]):
         await self.image_service_cog.encapsulated_send(
             user_id,
             prompt,
-            None,
+            interaction,
             msg,
             True,
             True,
diff --git a/models/openai_model.py b/models/openai_model.py
index 636c24d..a0ee481 100644
--- a/models/openai_model.py
+++ b/models/openai_model.py
@@ -414,7 +414,7 @@ class Model:
 
                 return response
 
-    async def send_image_request(self, prompt, vary=None) -> tuple[File, list[Any]]:
+    async def send_image_request(self, ctx, prompt, vary=None) -> tuple[File, list[Any]]:
         # Validate that  all the parameters are in a good state before we send the request
         words = len(prompt.split(" "))
         if words < 3 or words > 75:
@@ -537,17 +537,21 @@ class Model:
         )
 
         # Print the filesize of new_im, in mega bytes
-        image_size = os.path.getsize(temp_file.name) / 1000000
+        image_size = os.path.getsize(temp_file.name) / 1048576
+        if ctx.guild is None:
+            guild_file_limit = 8 
+        else:
+            guild_file_limit = ctx.guild.filesize_limit / 1048576
 
         # If the image size is greater than 8MB, we can't return this to the user, so we will need to downscale the
         # image and try again
         safety_counter = 0
-        while image_size > 8:
+        while image_size > guild_file_limit:
             safety_counter += 1
             if safety_counter >= 3:
                 break
             print(
-                f"Image size is {image_size}MB, which is too large for discord. Downscaling and trying again"
+                f"Image size is {image_size}MB, which is too large for this server {guild_file_limit}MB. Downscaling and trying again"
             )
             # We want to do this resizing asynchronously, so that it doesn't block the main thread during the resize.
             # We can use the asyncio.run_in_executor method to do this