diff --git a/python/ray/train/_internal/checkpoint.py b/python/ray/train/_internal/checkpoint.py
index 9f9bda77b3db2..39bcddc8fbcb8 100644
--- a/python/ray/train/_internal/checkpoint.py
+++ b/python/ray/train/_internal/checkpoint.py
@@ -214,7 +214,12 @@ def _load_checkpoint(
     ) -> Optional[Union[Dict, Checkpoint]]:
         loaded_checkpoint = super()._load_checkpoint(checkpoint_to_load)
         assert not loaded_checkpoint or isinstance(loaded_checkpoint, Checkpoint)
-        self._latest_checkpoint_id = getattr(loaded_checkpoint, TUNE_CHECKPOINT_ID, 0)
+        # `latest_checkpoint_id` will be the id assigned to the next checkpoint,
+        # which should be one more than the loaded checkpoint's id
+        # If no checkpoint is loaded, initialize this to 0
+        self._latest_checkpoint_id = (
+            getattr(loaded_checkpoint, TUNE_CHECKPOINT_ID, -1) + 1
+        )
         return loaded_checkpoint
 
     def add_tune_checkpoint_id(self, checkpoint: Checkpoint):