diff --git a/src/khoj/processor/conversation/utils.py b/src/khoj/processor/conversation/utils.py
index b0d401fa..ecd4f8ad 100644
--- a/src/khoj/processor/conversation/utils.py
+++ b/src/khoj/processor/conversation/utils.py
@@ -151,17 +151,20 @@ def truncate_messages(
         )
 
     system_message = messages.pop()
+    assert type(system_message.content) == str
     system_message_tokens = len(encoder.encode(system_message.content))
 
-    tokens = sum([len(encoder.encode(message.content)) for message in messages])
+    tokens = sum([len(encoder.encode(message.content)) for message in messages if type(message.content) == str])
     while (tokens + system_message_tokens) > max_prompt_size and len(messages) > 1:
         messages.pop()
-        tokens = sum([len(encoder.encode(message.content)) for message in messages])
+        assert type(system_message.content) == str
+        tokens = sum([len(encoder.encode(message.content)) for message in messages if type(message.content) == str])
 
     # Truncate current message if still over max supported prompt size by model
     if (tokens + system_message_tokens) > max_prompt_size:
-        current_message = "\n".join(messages[0].content.split("\n")[:-1])
-        original_question = "\n".join(messages[0].content.split("\n")[-1:])
+        assert type(system_message.content) == str
+        current_message = "\n".join(messages[0].content.split("\n")[:-1]) if type(messages[0].content) == str else ""
+        original_question = "\n".join(messages[0].content.split("\n")[-1:]) if type(messages[0].content) == str else ""
         original_question_tokens = len(encoder.encode(original_question))
         remaining_tokens = max_prompt_size - original_question_tokens - system_message_tokens
         truncated_message = encoder.decode(encoder.encode(current_message)[:remaining_tokens]).strip()
diff --git a/src/khoj/routers/api.py b/src/khoj/routers/api.py
index be2643bd..b384d8a3 100644
--- a/src/khoj/routers/api.py
+++ b/src/khoj/routers/api.py
@@ -296,7 +296,7 @@ async def get_all_filenames(
         client=client,
     )
 
-    return await sync_to_async(list)(EntryAdapters.aget_all_filenames_by_source(user, content_source))
+    return await sync_to_async(list)(EntryAdapters.aget_all_filenames_by_source(user, content_source))  # type: ignore[call-arg]
 
 
 @api.post("/config/data/conversation/model", status_code=200)