diff --git a/changelog.d/1847.bugfix.md b/changelog.d/1847.bugfix.md
new file mode 100644
index 0000000000..aa7638257f
--- /dev/null
+++ b/changelog.d/1847.bugfix.md
@@ -0,0 +1 @@
+Keep pipx startup usable when locked files prevent trash cleanup.
diff --git a/src/pipx/util.py b/src/pipx/util.py
index 8008d64f09..d0730f852c 100644
--- a/src/pipx/util.py
+++ b/src/pipx/util.py
@@ -53,8 +53,10 @@ def rmdir(path: Path, safe_rm: bool = True) -> None:
     # Windows doesn't let us delete or overwrite files that are being run
     # But it does let us rename/move it. To get around this issue, we can move
     # the file to a temporary folder (to be deleted at a later time)
-    # So, if safe_rm is True, we ignore any errors and move the file to the trash with below code
-    shutil.rmtree(path, ignore_errors=safe_rm)
+    # Always ignore errors so locked files don't make cleanup fatal. If the
+    # directory is still present afterwards, safe_rm controls whether it is
+    # moved to the trash or left in place with a warning.
+    shutil.rmtree(path, ignore_errors=True)
 
     # move it to be deleted later if it still exists
     if path.is_dir():
diff --git a/tests/test_util.py b/tests/test_util.py
index 5c2dcd9d08..04d7055e3d 100644
--- a/tests/test_util.py
+++ b/tests/test_util.py
@@ -1,10 +1,38 @@
 from __future__ import annotations
 
+import logging
 import sys
+from typing import TYPE_CHECKING
 
 import pytest
 
-from pipx.util import run_subprocess
+from pipx.util import rmdir, run_subprocess
+
+if TYPE_CHECKING:
+    from pathlib import Path
+
+
+def test_rmdir_without_safe_rm_is_non_fatal_for_locked_files(
+    caplog: pytest.LogCaptureFixture,
+    monkeypatch: pytest.MonkeyPatch,
+    tmp_path: Path,
+) -> None:
+    trash_dir = tmp_path / "trash"
+    trash_dir.mkdir()
+    (trash_dir / "locked.dll").write_text("locked")
+
+    def fake_rmtree(path: Path, ignore_errors: bool = False) -> None:
+        assert path == trash_dir
+        if not ignore_errors:
+            raise PermissionError("locked file")
+
+    monkeypatch.setattr("pipx.util.shutil.rmtree", fake_rmtree)
+
+    with caplog.at_level(logging.WARNING, logger="pipx.util"):
+        rmdir(trash_dir, safe_rm=False)
+
+    assert trash_dir.is_dir()
+    assert f"Failed to delete {trash_dir}. You may need to delete it manually." in caplog.text
 
 
 @pytest.mark.parametrize(