diff --git a/pyproject.toml b/pyproject.toml
index 8df96e4f..06338201 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -41,6 +41,7 @@ dependencies = [
     "fastapi == 0.77.1",
     "jinja2 == 3.1.2",
     "openai >= 0.27.0",
+    "tiktoken >= 0.3.0",
     "pillow == 9.3.0",
     "pydantic == 1.9.1",
     "pyqt6 == 6.3.1",
diff --git a/src/khoj/processor/conversation/gpt.py b/src/khoj/processor/conversation/gpt.py
index 14f02946..cfb236e5 100644
--- a/src/khoj/processor/conversation/gpt.py
+++ b/src/khoj/processor/conversation/gpt.py
@@ -247,6 +247,7 @@ Question: {user_query}"""
         conversation_primer,
         personality_primer,
         conversation_log,
+        model,
     )
 
     # Get Response from GPT
diff --git a/src/khoj/processor/conversation/utils.py b/src/khoj/processor/conversation/utils.py
index 69f47aff..b8728b6a 100644
--- a/src/khoj/processor/conversation/utils.py
+++ b/src/khoj/processor/conversation/utils.py
@@ -1,22 +1,44 @@
 # Standard Packages
 from datetime import datetime
 
+# External Packages
+import tiktoken
+
 # Internal Packages
 from khoj.utils.helpers import merge_dicts
 
 
-def generate_chatml_messages_with_context(user_message, system_message, conversation_log={}):
+max_prompt_size = {"gpt-3.5-turbo": 4096, "gpt-4": 8192}
+
+
+def generate_chatml_messages_with_context(
+    user_message, system_message, conversation_log={}, model_name="gpt-3.5-turbo", lookback_turns=2
+):
     """Generate messages for ChatGPT with context from previous conversation"""
     # Extract Chat History for Context
     chat_logs = [f'{chat["message"]}\n\nNotes:\n{chat.get("context","")}' for chat in conversation_log.get("chat", [])]
-    last_backnforth = reciprocal_conversation_to_chatml(chat_logs[-2:])
-    rest_backnforth = reciprocal_conversation_to_chatml(chat_logs[-4:-2])
+    rest_backnforths = []
+    # Extract in reverse chronological order
+    for user_msg, assistant_msg in zip(chat_logs[-2::-2], chat_logs[::-2]):
+        if len(rest_backnforths) >= 2 * lookback_turns:
+            break
+        rest_backnforths += reciprocal_conversation_to_chatml([user_msg, assistant_msg])[::-1]
 
     # Format user and system messages to chatml format
     system_chatml_message = [message_to_chatml(system_message, "system")]
     user_chatml_message = [message_to_chatml(user_message, "user")]
 
-    return rest_backnforth + system_chatml_message + last_backnforth + user_chatml_message
+    messages = user_chatml_message + rest_backnforths[:2] + system_chatml_message + rest_backnforths[2:]
+
+    # Truncate oldest messages from conversation history until under max supported prompt size by model
+    encoder = tiktoken.encoding_for_model(model_name)
+    tokens = sum([len(encoder.encode(value)) for message in messages for value in message.values()])
+    while tokens > max_prompt_size[model_name]:
+        messages.pop()
+        tokens = sum([len(encoder.encode(value)) for message in messages for value in message.values()])
+
+    # Return message in chronological order
+    return messages[::-1]
 
 
 def reciprocal_conversation_to_chatml(message_pair):
diff --git a/tests/test_chat_director.py b/tests/test_chat_director.py
index 44fd29be..5feaa3f3 100644
--- a/tests/test_chat_director.py
+++ b/tests/test_chat_director.py
@@ -47,7 +47,7 @@ def test_chat_with_no_chat_history_or_retrieved_content(chat_client):
     expected_responses = ["Khoj", "khoj"]
     assert response.status_code == 200
     assert any([expected_response in response_message for expected_response in expected_responses]), (
-        "Expected assistants name, [K|k]hoj, in response but got" + response_message
+        "Expected assistants name, [K|k]hoj, in response but got: " + response_message
     )
 
 
@@ -69,7 +69,7 @@ def test_answer_from_chat_history(chat_client):
     expected_responses = ["Testatron", "testatron"]
     assert response.status_code == 200
     assert any([expected_response in response_message for expected_response in expected_responses]), (
-        "Expected [T|t]estatron in response but got" + response_message
+        "Expected [T|t]estatron in response but got: " + response_message
     )