diff --git a/main.py b/main.py
index cb3a12b8..fcddd267 100644
--- a/main.py
+++ b/main.py
@@ -1,6 +1,7 @@
 import asyncio
 from absl import app, flags
 import logging
+import glob
 import os
 import sys
 import pickle
@@ -174,15 +175,29 @@ async def main():
                         except Exception as e:
                             print(f"Loading {filename} failed with: {e}")
                     else:
-                        print(f"/load error: no checkpoint specified")
+                        # Load the latest file 
+                        print(f"/load warning: no checkpoint specified, loading most recent checkpoint instead")
+                        json_files = glob.glob("saved_state/*.json")  # This will list all .json files in the current directory.
+        
+                        # Check if there are any json files.
+                        if not json_files:
+                            print(f"/load error: no .json checkpoint files found")
+                        else:
+                            # Sort files based on modified timestamp, with the latest file being the first.
+                            filename = max(json_files, key=os.path.getmtime)
+                            try:
+                                memgpt_agent.load_from_json_file_inplace(filename)
+                                print(f"Loaded checkpoint {filename}")
+                            except Exception as e:
+                                print(f"Loading {filename} failed with: {e}")
 
                     # need to load persistence manager too
                     filename = filename.replace('.json', '.persistence.pickle')
                     try:
                         memgpt_agent.persistence_manager = InMemoryStateManager.load(filename)  # TODO(fixme):for different types of persistence managers that require different load/save methods
-                        print(f"Loaded persistence manager from: {filename}")
+                        print(f"Loaded persistence manager from {filename}")
                     except Exception as e:
-                        print(f"/load error: loading persistence manager from {filename} failed with: {e}")
+                        print(f"/load warning: loading persistence manager from {filename} failed with: {e}")
 
                     continue