diff --git a/src/khoj/processor/org_mode/org_to_jsonl.py b/src/khoj/processor/org_mode/org_to_jsonl.py
index 0950a089..ed3be1d0 100644
--- a/src/khoj/processor/org_mode/org_to_jsonl.py
+++ b/src/khoj/processor/org_mode/org_to_jsonl.py
@@ -1,7 +1,6 @@
 # Standard Packages
 import glob
 import logging
-import time
 from typing import Iterable, List
 
 # Internal Packages
@@ -139,7 +138,14 @@ class OrgToJsonl(TextToJsonl):
                     logger.debug(f"Body: {parsed_entry.body}")
 
             if compiled:
-                entries += [Entry(compiled=compiled, raw=f"{parsed_entry}", file=f"{entry_to_file_map[parsed_entry]}")]
+                entries.append(
+                    Entry(
+                        compiled=compiled,
+                        raw=f"{parsed_entry}",
+                        heading=f"{parsed_entry.heading}",
+                        file=f"{entry_to_file_map[parsed_entry]}",
+                    )
+                )
 
         return entries
 
diff --git a/src/khoj/processor/text_to_jsonl.py b/src/khoj/processor/text_to_jsonl.py
index 22de2c01..e440af90 100644
--- a/src/khoj/processor/text_to_jsonl.py
+++ b/src/khoj/processor/text_to_jsonl.py
@@ -31,14 +31,30 @@ class TextToJsonl(ABC):
         "Split entries if compiled entry length exceeds the max tokens supported by the ML model."
         chunked_entries: List[Entry] = []
         for entry in entries:
+            # Split entry into words
             compiled_entry_words = [word for word in entry.compiled.split(" ") if word != ""]
+
             # Drop long words instead of having entry truncated to maintain quality of entry processed by models
             compiled_entry_words = [word for word in compiled_entry_words if len(word) <= max_word_length]
+
+            # Split entry into chunks of max tokens
             for chunk_index in range(0, len(compiled_entry_words), max_tokens):
                 compiled_entry_words_chunk = compiled_entry_words[chunk_index : chunk_index + max_tokens]
                 compiled_entry_chunk = " ".join(compiled_entry_words_chunk)
-                entry_chunk = Entry(compiled=compiled_entry_chunk, raw=entry.raw, file=entry.file)
-                chunked_entries.append(entry_chunk)
+
+                # Prepend heading to all other chunks, the first chunk already has heading from original entry
+                if chunk_index > 0:
+                    compiled_entry_chunk = f"{entry.heading}.\n{compiled_entry_chunk}"
+
+                chunked_entries.append(
+                    Entry(
+                        compiled=compiled_entry_chunk,
+                        raw=entry.raw,
+                        heading=entry.heading,
+                        file=entry.file,
+                    )
+                )
+
         return chunked_entries
 
     def mark_entries_for_update(
diff --git a/src/khoj/utils/rawconfig.py b/src/khoj/utils/rawconfig.py
index 389e80f6..6b87c220 100644
--- a/src/khoj/utils/rawconfig.py
+++ b/src/khoj/utils/rawconfig.py
@@ -103,11 +103,15 @@ class SearchResponse(ConfigBase):
 class Entry:
     raw: str
     compiled: str
+    heading: Optional[str]
     file: Optional[str]
 
-    def __init__(self, raw: str = None, compiled: str = None, file: Optional[str] = None):
+    def __init__(
+        self, raw: str = None, compiled: str = None, heading: Optional[str] = None, file: Optional[str] = None
+    ):
         self.raw = raw
         self.compiled = compiled
+        self.heading = heading
         self.file = file
 
     def to_json(self) -> str:
diff --git a/tests/test_jsonl_to_jsonl.py b/tests/test_jsonl_to_jsonl.py
index eb25d579..b52b5fc9 100644
--- a/tests/test_jsonl_to_jsonl.py
+++ b/tests/test_jsonl_to_jsonl.py
@@ -1,17 +1,13 @@
-# Standard Packages
-import json
-
 # Internal Packages
 from khoj.processor.jsonl.jsonl_to_jsonl import JsonlToJsonl
-from khoj.utils.jsonl import load_jsonl
 from khoj.utils.rawconfig import Entry
 
 
 def test_process_entries_from_single_input_jsonl(tmp_path):
     "Convert multiple jsonl entries from single file to entries."
     # Arrange
-    input_jsonl = """{"raw": "raw input data 1", "compiled": "compiled input data 1", "file": "source/file/path1"}
-{"raw": "raw input data 2", "compiled": "compiled input data 2", "file": "source/file/path2"}
+    input_jsonl = """{"raw": "raw input data 1", "compiled": "compiled input data 1", "heading": null, "file": "source/file/path1"}
+{"raw": "raw input data 2", "compiled": "compiled input data 2", "heading": null, "file": "source/file/path2"}
 """
     input_jsonl_file = create_file(tmp_path, input_jsonl)
 
@@ -29,8 +25,8 @@ def test_process_entries_from_single_input_jsonl(tmp_path):
 def test_process_entries_from_multiple_input_jsonls(tmp_path):
     "Convert multiple jsonl entries from single file to entries."
     # Arrange
-    input_jsonl_1 = """{"raw": "raw input data 1", "compiled": "compiled input data 1", "file": "source/file/path1"}"""
-    input_jsonl_2 = """{"raw": "raw input data 2", "compiled": "compiled input data 2", "file": "source/file/path2"}"""
+    input_jsonl_1 = """{"raw": "raw input data 1", "compiled": "compiled input data 1", "heading": null, "file": "source/file/path1"}"""
+    input_jsonl_2 = """{"raw": "raw input data 2", "compiled": "compiled input data 2", "heading": null, "file": "source/file/path2"}"""
     input_jsonl_file_1 = create_file(tmp_path, input_jsonl_1, filename="input1.jsonl")
     input_jsonl_file_2 = create_file(tmp_path, input_jsonl_2, filename="input2.jsonl")
 
diff --git a/tests/test_org_to_jsonl.py b/tests/test_org_to_jsonl.py
index aed4983f..15dd368a 100644
--- a/tests/test_org_to_jsonl.py
+++ b/tests/test_org_to_jsonl.py
@@ -62,9 +62,11 @@ def test_entry_split_when_exceeds_max_words(tmp_path):
 
     # Assert
     assert len(jsonl_data) == 2
+    # Ensure compiled entries split by max_words start with entry heading (for search context)
+    assert all(entry["compiled"].startswith("Heading") for entry in jsonl_data)
 
 
-def test_entry_split_drops_large_words(tmp_path):
+def test_entry_split_drops_large_words():
     "Ensure entries drops words larger than specified max word length from compiled version."
     # Arrange
     entry_text = f"""*** Heading