diff --git a/tests/utils/test_checkpoint.py b/tests/utils/test_checkpoint.py
index 6c4e86b53f..49be9560b3 100644
--- a/tests/utils/test_checkpoint.py
+++ b/tests/utils/test_checkpoint.py
@@ -10,7 +10,7 @@
 import shutil
 import tempfile
 import unittest
-from unittest.mock import patch
+from unittest.mock import MagicMock, patch
 
 import torch
 
@@ -787,6 +787,43 @@ def test_remove_worst_checkpoint(self) -> None:
             self.assertTrue(os.path.exists(os.path.join(temp_dir, "epoch_0_step_1")))
             self.assertEqual(ckpt_manager._ckpt_paths, [CheckpointPath(temp_dir, 0, 1)])
 
+    @patch(
+        "fsspec.implementations.local.LocalFileSystem.rm",
+        side_effect=Exception("OSError: [Errno 2] No such file or directory"),
+    )
+    def test_remove_worst_checkpoint_exception(self, mock_url_to_fs: MagicMock) -> None:
+        with tempfile.TemporaryDirectory() as temp_dir:
+            os.mkdir(os.path.join(temp_dir, "epoch_0_train_step_0"))
+            os.mkdir(os.path.join(temp_dir, "epoch_0_train_step_1"))
+
+            ckpt_manager = CheckpointManager(temp_dir, keep_last_n_checkpoints=2)
+
+            log_container = []
+            with patch(
+                "torchtnt.utils.checkpoint.logging.Logger.error", log_container.append
+            ):
+                ckpt_manager.append_checkpoint(
+                    CheckpointPath(temp_dir, 0, {Phase.TRAIN: 2})
+                )
+
+            self.assertEqual(
+                log_container,
+                [
+                    (
+                        f"Failed to remove checkpoint '{temp_dir}/epoch_0_train_step_0' for bookkeeping purposes. "
+                        "Do not use it to restore since it may be corrupted! Exception: OSError: [Errno 2] No such file or directory"
+                    )
+                ],
+            )
+            # Make sure we are not tracking the oldest one anymore, even if it was not deleted
+            self.assertEqual(
+                ckpt_manager._ckpt_paths,
+                [
+                    CheckpointPath(temp_dir, 0, {Phase.TRAIN: 1}),
+                    CheckpointPath(temp_dir, 0, {Phase.TRAIN: 2}),
+                ],
+            )
+
 
 class CheckpointUtilsTest(unittest.TestCase):
     @staticmethod
diff --git a/torchtnt/utils/checkpoint.py b/torchtnt/utils/checkpoint.py
index 149dcb1302..e13fcf7e3d 100644
--- a/torchtnt/utils/checkpoint.py
+++ b/torchtnt/utils/checkpoint.py
@@ -487,7 +487,7 @@ def append_checkpoint(self, ckpt: CheckpointPath) -> None:
             ckpt: The checkpoint to save.
             state: The training state.
         """
-        # Remove oldest checkpoint if needed
+        # Remove oldest/worst checkpoint if needed
         max_ckpts = self._keep_last_n_checkpoints
         if max_ckpts and len(self._ckpt_paths) >= max_ckpts:
             self.remove_checkpoint()
@@ -542,7 +542,15 @@ def remove_checkpoint(self) -> None:
         worst_ckpt_path = self._ckpt_paths.pop(0)
         if self._pg_wrapper.get_rank() == 0:
             fs, _ = url_to_fs(self.dirpath)
-            fs.rm(worst_ckpt_path.path, recursive=True)
+            try:
+                fs.rm(worst_ckpt_path.path, recursive=True)
+            except Exception as exc:
+                logger.error(
+                    (
+                        f"Failed to remove checkpoint '{worst_ckpt_path}' for bookkeeping purposes. "
+                        f"Do not use it to restore since it may be corrupted! Exception: {exc}"
+                    )
+                )
 
 
 @rank_zero_read_and_broadcast