diff --git a/backend/open_webui/routers/retrieval.py b/backend/open_webui/routers/retrieval.py
index fcda8883ec..4864845e8d 100644
--- a/backend/open_webui/routers/retrieval.py
+++ b/backend/open_webui/routers/retrieval.py
@@ -10,7 +10,7 @@ import shutil
 import uuid
 from datetime import datetime
 from pathlib import Path
-from typing import Callable, Iterator, Optional, Sequence, Union
+from typing import Callable, Iterator, Literal, Optional, Sequence, Union
 
 import tiktoken
 from fastapi import (
@@ -653,7 +653,7 @@ class ConfigForm(BaseModel):
     TOP_K: int | None = None
     BYPASS_EMBEDDING_AND_RETRIEVAL: bool | None = None
     RAG_FULL_CONTEXT: bool | None = None
-    RAG_FILE_CONTEXT_SCOPE: str | None = None
+    RAG_FILE_CONTEXT_SCOPE: Literal['conversation', 'message'] | None = None
 
     # Hybrid search settings
     ENABLE_RAG_HYBRID_SEARCH: bool | None = None
diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index be6c08b25c..2e084ca1a2 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -955,11 +955,17 @@ def get_source_context(sources: list, source_ids: dict = None, include_content:
     return context_string
 
 
+FILE_CONTEXT_ITEM_TYPES = {'doc', 'text', 'note', 'chat', 'folder', 'collection'}
+
+
 def is_file_context_item(item: dict) -> bool:
     if not isinstance(item, dict):
         return False
 
-    return item.get('type') != 'image' and not (item.get('content_type') or '').startswith('image/')
+    item_type = item.get('type')
+    return item_type in FILE_CONTEXT_ITEM_TYPES or (
+        item_type == 'file' and not (item.get('content_type') or '').startswith('image/')
+    )
 
 
 def get_file_context_key(item: dict) -> tuple:
diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index 28e428971d..5bf538f21a 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -2340,7 +2340,7 @@
 					return {
 						role: message.role,
 						...(message.output ? { output: message.output } : {}),
-						...(messageFiles.length > 0 ? { files: messageFiles } : {}),
+						...(message.role === 'user' && messageFiles.length > 0 ? { files: messageFiles } : {}),
 						...(message.role === 'user' && imageFiles.length > 0
 							? {
 									content: [