diff --git a/casanovo/casanovo.py b/casanovo/casanovo.py
index bdeb9766..f9c37f08 100644
--- a/casanovo/casanovo.py
+++ b/casanovo/casanovo.py
@@ -96,7 +96,7 @@ def __init__(self, *args, **kwargs) -> None:
                 default="info",
             ),
             click.Option(
-                ("-f", "--overwrite"),
+                ("-f", "--force_overwrite"),
                 help="Whether to overwrite output files.",
                 is_flag=True,
                 show_default=True,
@@ -159,7 +159,7 @@ def sequence(
     output_dir: Optional[str],
     output_root: Optional[str],
     verbosity: str,
-    overwrite: bool,
+    force_overwrite: bool,
     evaluate: bool,
 ) -> None:
     """De novo sequence peptides from tandem mass spectra.
@@ -168,11 +168,13 @@ def sequence(
     to sequence peptides. If evaluate is set to True PEAK_PATH must be
     one or more annotated MGF file.
     """
-    output, output_dir = _resolve_output(output_dir, output_root, verbosity)
-    if output_root is not None and not overwrite:
-        file_pattern = re.escape(output_root) + r"\.(?:log|mztab)"
-        utils.check_dir(output_dir, [file_pattern])
+    file_patterns = list()
+    if output_root is not None and not force_overwrite:
+        file_patterns = [f"{output_root}.log", f"{output_root}.mztab"]
 
+    output, output_dir = _resolve_output(
+        output_dir, output_root, file_patterns, verbosity
+    )
     config, model = setup_model(model, config, output, False)
     start_time = time.time()
     with ModelRunner(config, model, output_root, output_dir, False) as runner:
@@ -216,21 +218,24 @@ def train(
     output_dir: Optional[str],
     output_root: Optional[str],
     verbosity: str,
-    overwrite: bool,
+    force_overwrite: bool,
 ) -> None:
     """Train a Casanovo model on your own data.
 
     TRAIN_PEAK_PATH must be one or more annoated MGF files, such as those
     provided by MassIVE-KB, from which to train a new Casnovo model.
     """
-    output, output_dir = _resolve_output(output_dir, output_root, verbosity)
-    if output_root is not None and not overwrite:
-        utils.check_dir(output_dir, [re.escape(output_root) + r"\.log"])
+    file_patterns = list()
+    if output_root is not None and not force_overwrite:
+        file_patterns = [f"{output_root}.log"]
 
+    output, output_dir = _resolve_output(
+        output_dir, output_root, file_patterns, verbosity
+    )
     config, model = setup_model(model, config, output, True)
     start_time = time.time()
     with ModelRunner(
-        config, model, output_root, output_dir, not overwrite
+        config, model, output_root, output_dir, not force_overwrite
     ) as runner:
         logger.info("Training a model from:")
         for peak_file in train_peak_path:
@@ -520,12 +525,37 @@ def _get_model_weights(cache_dir: Path) -> str:
 def _resolve_output(
     output_dir: str | None,
     output_root: str | None,
+    file_patterns: list[str],
     verbosity: str,
 ) -> Tuple[Path, str]:
+    """
+    Resolves the output directory and sets up logging.
+
+    Parameters:
+    -----------
+    output_dir : str | None
+        The path to the output directory. If `None`, the current working
+        directory will be used.
+    output_root : str | None
+        The base name for the output files. If `None`, no specific base name is
+        set, and logging will be configured accordingly to the behavior of
+        `setup_logging`.
+    file_patterns : list[str]
+        A list of file patterns that should be checked within the `output_dir`.
+    verbosity : str
+        The verbosity level for logging.
+
+    Returns:
+    --------
+    Tuple[Path, str]
+        The output directory and the base name for log and results files (if
+        applicable).
+    """
     output_dir = Path(output_dir) if output_dir is not None else Path.cwd()
     output_base_name = (
         None if output_root is None else (output_dir / output_root)
     )
+    utils.check_dir(output_dir, file_patterns)
     output = setup_logging(output_base_name, verbosity)
     return output, output_dir
 
diff --git a/casanovo/denovo/model_runner.py b/casanovo/denovo/model_runner.py
index ff441179..5c8833de 100644
--- a/casanovo/denovo/model_runner.py
+++ b/casanovo/denovo/model_runner.py
@@ -71,13 +71,13 @@ def __init__(
         )
 
         if overwrite_ckpt_check:
-            patterns = [r"epoch=\d+\-step=\d+\.ckpt", r"best\.ckpt"]
-            if output_rootname is not None:
-                patterns = [
-                    re.escape(output_rootname + ".") + pattern
-                    for pattern in patterns
-                ]
-            utils.check_dir(output_dir, patterns)
+            utils.check_dir(
+                output_dir,
+                [
+                    f"{curr_filename.format(epoch='*', step='*')}.ckpt",
+                    f"{best_filename}.ckpt",
+                ],
+            )
 
         # Configure checkpoints.
         self.callbacks = [
diff --git a/casanovo/utils.py b/casanovo/utils.py
index 3d778791..fb0c3327 100644
--- a/casanovo/utils.py
+++ b/casanovo/utils.py
@@ -256,9 +256,7 @@ def log_sequencing_report(
         )
 
 
-def check_dir(
-    dir: pathlib.Path, file_patterns: Iterable[re.Pattern[str]]
-) -> None:
+def check_dir(dir: pathlib.Path, file_patterns: Iterable[str]) -> None:
     """
     Check that no file names in dir match any of file_patterns
 
@@ -266,8 +264,8 @@ def check_dir(
     ----------
     dir : pathlib.Path
         The directory to check for matching file names
-    file_patterns : Iterable[re.Pattern[str]]
-        File name re patterns to test file names against
+    file_patterns : Iterable[str]
+        UNIX style wildcard pattern to test file names against
 
     Raises
     ------
@@ -275,13 +273,9 @@ def check_dir(
         If matching file name is found in dir
     """
     for pattern in file_patterns:
-        comp_pattern = re.compile(pattern)
-        for file in dir.iterdir():
-            if not file.is_file():
-                continue
-
-            if comp_pattern.fullmatch(file.name) is not None:
-                raise FileExistsError(
-                    f"File {file.name} already exists in {dir} "
-                    "and can not be overwritten."
-                )
+        matches = list(dir.glob(pattern))
+        if len(matches) > 0:
+            raise FileExistsError(
+                f"File {matches[0].name} already exists in {dir} "
+                "and can not be overwritten."
+            )
diff --git a/tests/test_integration.py b/tests/test_integration.py
index ded8294d..bb6ef66e 100644
--- a/tests/test_integration.py
+++ b/tests/test_integration.py
@@ -3,7 +3,6 @@
 from pathlib import Path
 
 import pyteomics.mztab
-import pytest
 from click.testing import CliRunner
 
 from casanovo import casanovo
@@ -44,10 +43,6 @@ def test_train_and_run(
     assert model_file.exists()
     assert best_model.exists()
 
-    # Check that re-running train fails due to no overwrite
-    with pytest.raises(FileExistsError):
-        run(train_args)
-
     assert model_file.exists()
     assert best_model.exists()
 
@@ -90,12 +85,6 @@ def test_train_and_run(
     assert psms.loc[4, "sequence"] == "PEPTLDEK"
     assert psms.loc[4, "spectra_ref"] == "ms_run[2]:scan=111"
 
-    # Verify that running predict again fails due to no overwrite
-    with pytest.raises(FileExistsError):
-        run(predict_args)
-
-    assert output_filename.is_file()
-
     # Finally, try evaluating:
     output_rootname = "test-eval"
     output_filename = (tmp_path / output_rootname).with_suffix(".mztab")
@@ -156,10 +145,6 @@ def test_train_and_run(
         ]
     )
 
-    # Verify that running again fails due to no overwrite
-    with pytest.raises(FileExistsError):
-        run(eval_args)
-
     assert output_filename.is_file()
 
 
diff --git a/tests/unit_tests/test_runner.py b/tests/unit_tests/test_runner.py
index f31725ff..8cea9021 100644
--- a/tests/unit_tests/test_runner.py
+++ b/tests/unit_tests/test_runner.py
@@ -121,12 +121,17 @@ def test_save_and_load_weights_deprecated(tmp_path, mgf_small, tiny_config):
     torch.save(ckpt_data, str(ckpt))
 
     # Inference.
-    with ModelRunner(config=config, model_filename=str(ckpt)) as runner:
+    with ModelRunner(
+        config=config, model_filename=str(ckpt), overwrite_ckpt_check=False
+    ) as runner:
         runner.initialize_model(train=False)
         assert runner.model.cosine_schedule_period_iters == 5
     # Fine-tuning.
     with ModelRunner(
-        config=config, model_filename=str(ckpt), output_dir=tmp_path
+        config=config,
+        model_filename=str(ckpt),
+        output_dir=tmp_path,
+        overwrite_ckpt_check=False,
     ) as runner:
         with pytest.warns(DeprecationWarning):
             runner.train([mgf_small], [mgf_small])
@@ -149,7 +154,9 @@ def test_calculate_precision(tmp_path, mgf_small, tiny_config):
     assert "valid_pep_precision" not in runner.model.history.columns
 
     config.calculate_precision = True
-    runner = ModelRunner(config=config, output_dir=tmp_path)
+    runner = ModelRunner(
+        config=config, output_dir=tmp_path, overwrite_ckpt_check=False
+    )
     with runner:
         runner.train([mgf_small], [mgf_small])
 
diff --git a/tests/unit_tests/test_unit.py b/tests/unit_tests/test_unit.py
index 33f20bf5..8cdd291d 100644
--- a/tests/unit_tests/test_unit.py
+++ b/tests/unit_tests/test_unit.py
@@ -924,9 +924,9 @@ def test_run_map(mgf_small):
 
 def test_check_dir(tmp_path):
     exists_path = tmp_path / "exists-1234.ckpt"
-    exists_pattern = r"exists\-\d+\.ckpt"
+    exists_pattern = "exists-*.ckpt"
     exists_path.touch()
-    dne_pattern = r"dne\-\d+\.ckpt"
+    dne_pattern = "dne-*.ckpt"
 
     with pytest.raises(FileExistsError):
         utils.check_dir(tmp_path, [exists_pattern, dne_pattern])