diff --git a/src/paperless_ai/chat.py b/src/paperless_ai/chat.py
index 10d2b96d8..7942321a6 100644
--- a/src/paperless_ai/chat.py
+++ b/src/paperless_ai/chat.py
@@ -85,6 +85,10 @@ def stream_chat_with_documents(query_str: str, documents: list[Document]):
 
 
 def _stream_chat_with_documents(query_str: str, documents: list[Document]):
+    if not documents:
+        yield CHAT_NO_CONTENT_MESSAGE
+        return
+
     from llama_index.core.prompts import PromptTemplate
     from llama_index.core.query_engine import RetrieverQueryEngine
     from llama_index.core.response_synthesizers import get_response_synthesizer
diff --git a/src/paperless_ai/tests/test_chat.py b/src/paperless_ai/tests/test_chat.py
index 52e36b15a..bb32c62ae 100644
--- a/src/paperless_ai/tests/test_chat.py
+++ b/src/paperless_ai/tests/test_chat.py
@@ -176,6 +176,13 @@ def test_stream_chat_with_multiple_documents_retrieval(patch_embed_nodes) -> Non
         )
 
 
+def test_stream_chat_empty_document_list() -> None:
+    with patch("paperless_ai.chat.load_or_build_index") as mock_load_index:
+        output = list(stream_chat_with_documents("Any info?", []))
+        mock_load_index.assert_not_called()
+        assert output == ["Sorry, I couldn't find any content to answer your question."]
+
+
 def test_stream_chat_no_matching_nodes() -> None:
     with (
         patch("paperless_ai.chat.AIClient") as mock_client_cls,