diff --git a/src/ape/utils/os.py b/src/ape/utils/os.py
index 6a3a4213df..07419df681 100644
--- a/src/ape/utils/os.py
+++ b/src/ape/utils/os.py
@@ -1,6 +1,7 @@
 import json
 import os
 import re
+import stat
 import sys
 import tarfile
 import zipfile
@@ -372,6 +373,14 @@ def extract_archive(archive_file: Path, destination: Optional[Path] = None):
         raise ValueError(f"Unsupported zip format: '{archive_file.suffix}'.")
 
 
+def _remove_readonly(func, path, excinfo):
+    """
+    Error handler for shutil.rmtree that handles removing read-only files.
+    """
+    os.chmod(path, stat.S_IWRITE)
+    func(path)
+
+
 class CacheDirectory:
     """
     A directory for caching data where each data item is named
diff --git a/src/ape_pm/dependency.py b/src/ape_pm/dependency.py
index 6e0828c90f..657a6441c0 100644
--- a/src/ape_pm/dependency.py
+++ b/src/ape_pm/dependency.py
@@ -16,7 +16,7 @@
 from ape.managers.project import _version_to_options
 from ape.utils._github import _GithubClient, github_client
 from ape.utils.basemodel import ManagerAccessMixin
-from ape.utils.os import clean_path, extract_archive, get_package_path, in_tempdir
+from ape.utils.os import _remove_readonly, clean_path, extract_archive, get_package_path, in_tempdir
 
 
 def _fetch_local(src: Path, destination: Path, config_override: Optional[dict] = None):
@@ -204,8 +204,12 @@ def __repr__(self) -> str:
     def fetch(self, destination: Path):
         destination.parent.mkdir(exist_ok=True, parents=True)
         if ref := self.ref:
+            # NOTE: destination path should not exist at this point,
+            #   so delete it in case it's left over from a failure.
+            if destination.is_dir():
+                shutil.rmtree(destination)
+
             # Fetch using git-clone approach (by git-reference).
-            # NOTE: destination path does not exist at this point.
             self._fetch_ref(ref, destination)
         else:
             # Fetch using Version API from GitHub.
@@ -222,7 +226,8 @@ def fetch(self, destination: Path):
                 # NOTE: When using ref-from-a-version, ensure
                 #   it didn't create the destination along the way;
                 #   else, the ref is cloned in the wrong spot.
-                shutil.rmtree(destination, ignore_errors=True)
+                if destination.is_dir():
+                    shutil.rmtree(destination, onerror=_remove_readonly)
                 try:
                     self._fetch_ref(version, destination)
                 except Exception:
diff --git a/tests/functional/test_dependencies.py b/tests/functional/test_dependencies.py
index a89a7451e9..58f7987ceb 100644
--- a/tests/functional/test_dependencies.py
+++ b/tests/functional/test_dependencies.py
@@ -1,4 +1,5 @@
 import json
+import os
 import shutil
 from pathlib import Path
 
@@ -611,6 +612,24 @@ def test_fetch_ref(self, mock_client):
             "ApeWorX", "ApeNotAThing", path, branch="3.0.0"
         )
 
+    def test_fetch_existing_destination_with_read_only_files(self, mock_client):
+        """
+        Show it handles when the destination contains read-only files already
+        """
+        dependency = GithubDependency(github="ApeWorX/ApeNotAThing", ref="3.0.0", name="apetestdep")
+        dependency._github_client = mock_client
+
+        with create_tempdir() as path:
+            readonly_file = path / "readme.txt"
+            readonly_file.write_text("readme!")
+
+            # NOTE: This only makes a difference on Windows. If using a UNIX system,
+            #   rmtree still deletes readonly files regardless. Windows is more restrictive.
+            os.chmod(readonly_file, 0o444)  # Read-only permissions
+
+            dependency.fetch(path)
+            assert not readonly_file.is_file()
+
 
 class TestPythonDependency:
     @pytest.fixture(scope="class", params=("site_package", "python", "pypi"))