diff --git a/routes/__pycache__/conversations.cpython-313.pyc b/routes/__pycache__/conversations.cpython-313.pyc
index 7b749cf..5f57099 100644
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diff --git a/routes/__pycache__/main.cpython-313.pyc b/routes/__pycache__/main.cpython-313.pyc
index 7f90ded..c453e41 100644
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diff --git a/routes/conversations.py b/routes/conversations.py
index c07de7d..4f6acea 100644
--- a/routes/conversations.py
+++ b/routes/conversations.py
@@ -328,8 +328,21 @@ def delete_conversation(conversation_id):
     )
     db.session.commit()
     
+    # Get all messages in the conversation
+    messages = Message.query.filter_by(conversation_id=conversation_id).all()
+    
+    # Delete attachments and their files first
+    for message in messages:
+        for attachment in message.attachments:
+            # Delete the physical file
+            if os.path.exists(attachment.path):
+                os.remove(attachment.path)
+            # Delete the attachment record
+            db.session.delete(attachment)
+    
     # Delete all messages in the conversation
-    Message.query.filter_by(conversation_id=conversation_id).delete()
+    for message in messages:
+        db.session.delete(message)
     
     # Delete the conversation
     db.session.delete(conversation)
diff --git a/uploads/Screenshot_2025-05-27_103137.png b/uploads/Screenshot_2025-05-27_103137.png
deleted file mode 100644
index 11f9e13..0000000
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diff --git a/uploads/test.png b/uploads/test.png
deleted file mode 100644
index eb5fc48..0000000
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