diff --git a/src/processor/text_to_jsonl.py b/src/processor/text_to_jsonl.py
index 2f5e7e40..0eb60e6c 100644
--- a/src/processor/text_to_jsonl.py
+++ b/src/processor/text_to_jsonl.py
@@ -23,6 +23,19 @@ class TextToJsonl(ABC):
     def hash_func(key: str) -> Callable:
         return lambda entry: hashlib.md5(bytes(getattr(entry, key), encoding='utf-8')).hexdigest()
 
+    @staticmethod
+    def split_entries_by_max_tokens(entries: list[Entry], max_tokens: int=256) -> list[Entry]:
+        "Split entries if compiled entry length exceeds the max tokens supported by the ML model."
+        chunked_entries: list[Entry] = []
+        for entry in entries:
+            compiled_entry_words = entry.compiled.split()
+            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)
+        return chunked_entries
+
     def mark_entries_for_update(self, current_entries: list[Entry], previous_entries: list[Entry], key='compiled', logger=None) -> list[tuple[int, Entry]]:
         # Hash all current and previous entries to identify new entries
         start = time.time()
diff --git a/tests/test_org_to_jsonl.py b/tests/test_org_to_jsonl.py
index 2dbedcd0..ee9aae16 100644
--- a/tests/test_org_to_jsonl.py
+++ b/tests/test_org_to_jsonl.py
@@ -3,6 +3,7 @@ import json
 
 # Internal Packages
 from src.processor.org_mode.org_to_jsonl import OrgToJsonl
+from src.processor.text_to_jsonl import TextToJsonl
 from src.utils.helpers import is_none_or_empty
 
 
@@ -35,6 +36,34 @@ 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):
+    "Ensure entries with compiled words exceeding max_words are split."
+    # Arrange
+    entry = f'''*** Heading
+    :PROPERTIES:
+    :ID:       42-42-42
+    :END:
+    \t\r
+    Body Line 1
+    '''
+    orgfile = create_file(tmp_path, entry)
+
+    # Act
+    # Extract Entries from specified Org files
+    entries, entry_to_file_map = OrgToJsonl.extract_org_entries(org_files=[orgfile])
+
+    # Split Each Entry from specified Org files by Max Words
+    jsonl_string = OrgToJsonl.convert_org_entries_to_jsonl(
+        TextToJsonl.split_entries_by_max_tokens(
+            OrgToJsonl.convert_org_nodes_to_entries(entries, entry_to_file_map),
+            max_tokens = 2)
+        )
+    jsonl_data = [json.loads(json_string) for json_string in jsonl_string.splitlines()]
+
+    # Assert
+    assert len(jsonl_data) == 2
+
+
 def test_entry_with_body_to_jsonl(tmp_path):
     "Ensure entries with valid body text are loaded."
     # Arrange