diff --git a/src/metatrain/cli/train.py b/src/metatrain/cli/train.py
index 5523b6ef..29de6b1a 100644
--- a/src/metatrain/cli/train.py
+++ b/src/metatrain/cli/train.py
@@ -98,6 +98,29 @@ def _prepare_train_model_args(args: argparse.Namespace) -> None:
     args.options = OmegaConf.merge(args.options, override_options)
 
 
+def _process_continue_from(continue_from: Optional[str]) -> Optional[str]:
+    # covers the case where `continue_from` is `auto`
+    if continue_from == "auto":
+        # try to find the `outputs` directory; if it doesn't exist
+        # then we are not continuing from a previous run
+        if Path("outputs/").exists():
+            # take the latest day directory
+            dir = sorted(Path("outputs/").iterdir())[-1]
+            # take the latest second directory
+            dir = sorted(dir.iterdir())[-1]
+            # take the latest checkpoint. This cannot be done with
+            # `sorted` because some checkpoint files are named with
+            # the epoch number (e.g. `epoch_10.ckpt` would be before
+            # `epoch_8.ckpt`). We therefore sort by file creation time.
+            continue_from = str(
+                sorted(dir.glob("*.ckpt"), key=lambda f: f.stat().st_ctime)[-1]
+            )
+        else:
+            continue_from = None
+
+    return continue_from
+
+
 def train_model(
     options: Union[DictConfig, Dict],
     output: str = "model.pt",
@@ -334,6 +357,7 @@ def train_model(
 
     logger.info("Setting up model")
     try:
+        continue_from = _process_continue_from(continue_from)
         if continue_from is not None:
             logger.info(f"Loading checkpoint from `{continue_from}`")
             trainer = Trainer.load_checkpoint(continue_from, hypers["training"])
diff --git a/tests/cli/test_train_model.py b/tests/cli/test_train_model.py
index a6abc91e..dc3abcd6 100644
--- a/tests/cli/test_train_model.py
+++ b/tests/cli/test_train_model.py
@@ -421,6 +421,52 @@ def test_continue(options, monkeypatch, tmp_path):
     train_model(options, continue_from=MODEL_PATH_64_BIT)
 
 
+def test_continue_auto(options, caplog, monkeypatch, tmp_path):
+    """Test that continuing with the `auto` keyword results in
+    a continuation from the most recent checkpoint."""
+    monkeypatch.chdir(tmp_path)
+    shutil.copy(DATASET_PATH_QM9, "qm9_reduced_100.xyz")
+    caplog.set_level(logging.INFO)
+
+    # Make up an output directory with some checkpoints
+    true_checkpoint_dir = Path("outputs/2021-09-02/00-10-05")
+    true_checkpoint_dir.mkdir(parents=True, exist_ok=True)
+    # as well as some lower-priority checkpoints
+    fake_checkpoints_dirs = [
+        Path("outputs/2021-08-01/00-00-00"),
+        Path("outputs/2021-09-01/00-00-00"),
+        Path("outputs/2021-09-02/00-00-00"),
+        Path("outputs/2021-09-02/00-10-00"),
+    ]
+    for fake_checkpoint_dir in fake_checkpoints_dirs:
+        fake_checkpoint_dir.mkdir(parents=True, exist_ok=True)
+
+    for i in range(1, 4):
+        shutil.copy(MODEL_PATH_64_BIT, true_checkpoint_dir / f"model_{i}.ckpt")
+        # print content of the directory
+        print(f"true_checkpoint_dir content: {list(true_checkpoint_dir.iterdir())}")
+        for fake_checkpoint_dir in fake_checkpoints_dirs:
+            shutil.copy(MODEL_PATH_64_BIT, fake_checkpoint_dir / f"model_{i}.ckpt")
+
+    train_model(options, continue_from="auto")
+
+    assert "Loading checkpoint from" in caplog.text
+    assert str(true_checkpoint_dir) in caplog.text
+    assert "model_3.ckpt" in caplog.text
+
+
+def test_continue_auto_no_outputs(options, caplog, monkeypatch, tmp_path):
+    """Test that continuing with the `auto` keyword results in
+    training from scratch if `outputs/` is not present."""
+    monkeypatch.chdir(tmp_path)
+    shutil.copy(DATASET_PATH_QM9, "qm9_reduced_100.xyz")
+    caplog.set_level(logging.INFO)
+
+    train_model(options, continue_from="auto")
+
+    assert "Loading checkpoint from" not in caplog.text
+
+
 def test_continue_different_dataset(options, monkeypatch, tmp_path):
     """Test that continuing training from a checkpoint runs without an error raise
     with a different dataset than the original."""