diff --git a/libraries/python/assistant-extensions/assistant_extensions/attachments/_attachments.py b/libraries/python/assistant-extensions/assistant_extensions/attachments/_attachments.py
index 9d7af16f..8656424a 100644
--- a/libraries/python/assistant-extensions/assistant_extensions/attachments/_attachments.py
+++ b/libraries/python/assistant-extensions/assistant_extensions/attachments/_attachments.py
@@ -186,7 +186,7 @@ async def get_completion_messages_for_attachments(
                 ]
 
             messages.append({
-                "role": "user",
+                "role": "system",
                 "content": content,
             })
 
diff --git a/libraries/python/assistant-extensions/assistant_extensions/attachments/tests/test_attachments.py b/libraries/python/assistant-extensions/assistant_extensions/attachments/tests/test_attachments.py
index ea9330e1..83e7bfaf 100644
--- a/libraries/python/assistant-extensions/assistant_extensions/attachments/tests/test_attachments.py
+++ b/libraries/python/assistant-extensions/assistant_extensions/attachments/tests/test_attachments.py
@@ -26,11 +26,11 @@
                     "content": AttachmentsConfigModel().context_description,
                 },
                 {
-                    "role": "user",
+                    "role": "system",
                     "content": "<ATTACHMENT><FILENAME>file1.txt</FILENAME><CONTENT>file 1</CONTENT></ATTACHMENT>",
                 },
                 {
-                    "role": "user",
+                    "role": "system",
                     "content": "<ATTACHMENT><FILENAME>file2.txt</FILENAME><CONTENT>file 2</CONTENT></ATTACHMENT>",
                 },
             ],
@@ -46,11 +46,11 @@
                     "content": AttachmentsConfigModel().context_description,
                 },
                 {
-                    "role": "user",
+                    "role": "system",
                     "content": "<ATTACHMENT><FILENAME>file1.txt</FILENAME><ERROR>error processing file: file 1 error</ERROR><CONTENT></CONTENT></ATTACHMENT>",
                 },
                 {
-                    "role": "user",
+                    "role": "system",
                     "content": "<ATTACHMENT><FILENAME>file2.txt</FILENAME><CONTENT>file 2</CONTENT></ATTACHMENT>",
                 },
             ],
diff --git a/libraries/python/openai-client/openai_client/tokens.py b/libraries/python/openai-client/openai_client/tokens.py
index e85e98d0..a09f5762 100644
--- a/libraries/python/openai-client/openai_client/tokens.py
+++ b/libraries/python/openai-client/openai_client/tokens.py
@@ -183,8 +183,8 @@ def get_image_dims(image_uri: str) -> tuple[int, int]:
     # From https://github.com/openai/openai-cookbook/pull/881/files
     if re.match(r"data:image\/\w+;base64", image_uri):
         image_uri = re.sub(r"data:image\/\w+;base64,", "", image_uri)
-        image = Image.open(BytesIO(base64.b64decode(image_uri)))
-        return image.size
+        with Image.open(BytesIO(base64.b64decode(image_uri))) as image:
+            return image.size
     else:
         raise ValueError("Image must be a base64 string.")