diff --git a/src/khoj/processor/org_mode/org_to_entries.py b/src/khoj/processor/org_mode/org_to_entries.py
index 04ce97e4..c84ab48f 100644
--- a/src/khoj/processor/org_mode/org_to_entries.py
+++ b/src/khoj/processor/org_mode/org_to_entries.py
@@ -100,12 +100,13 @@ class OrgToEntries(TextToEntries):
                 continue
 
             todo_str = f"{parsed_entry.todo} " if parsed_entry.todo else ""
-            # Prepend filename as top heading to entry
-            filename = Path(entry_to_file_map[parsed_entry]).stem
+
+            # Prepend ancestor headings, filename as top heading to entry for context
+            ancestors_trail = " / ".join(parsed_entry.ancestors) or Path(entry_to_file_map[parsed_entry])
             if parsed_entry.heading:
-                heading = f"* {filename}\n** {todo_str}{parsed_entry.heading}."
+                heading = f"* Path: {ancestors_trail}\n** {todo_str}{parsed_entry.heading}."
             else:
-                heading = f"* {filename}."
+                heading = f"* Path: {ancestors_trail}."
 
             compiled = heading
             if state.verbose > 2:
diff --git a/tests/test_org_to_entries.py b/tests/test_org_to_entries.py
index 1eddcf95..76e2a8a7 100644
--- a/tests/test_org_to_entries.py
+++ b/tests/test_org_to_entries.py
@@ -45,9 +45,10 @@ def test_configure_heading_entry_to_jsonl(tmp_path):
             assert is_none_or_empty(jsonl_data)
 
 
-def test_entry_split_when_exceeds_max_words(tmp_path):
+def test_entry_split_when_exceeds_max_words():
     "Ensure entries with compiled words exceeding max_words are split."
     # Arrange
+    tmp_path = "/tmp/test.org"
     entry = f"""*** Heading
     \t\r
     Body Line
@@ -55,7 +56,7 @@ def test_entry_split_when_exceeds_max_words(tmp_path):
     data = {
         f"{tmp_path}": entry,
     }
-    expected_heading = f"* {tmp_path.stem}\n** Heading"
+    expected_heading = f"* Path: {tmp_path}\n** Heading"
 
     # Act
     # Extract Entries from specified Org files