diff --git a/distutils/command/install_data.py b/distutils/command/install_data.py
index 624c0b90..bd2932ab 100644
--- a/distutils/command/install_data.py
+++ b/distutils/command/install_data.py
@@ -5,8 +5,13 @@
 
 # contributed by Bastian Kleineidam
 
+from __future__ import annotations
+
+import functools
 import os
 
+from typing import Iterable
+
 from ..core import Command
 from ..util import change_root, convert_path
 
@@ -46,36 +51,42 @@ def finalize_options(self):
     def run(self):
         self.mkpath(self.install_dir)
         for f in self.data_files:
-            if isinstance(f, str):
-                # it's a simple file, so copy it
-                f = convert_path(f)
-                if self.warn_dir:
-                    self.warn(
-                        "setup script did not provide a directory for "
-                        f"'{f}' -- installing right in '{self.install_dir}'"
-                    )
-                (out, _) = self.copy_file(f, self.install_dir)
+            self._copy(f)
+
+    @functools.singledispatchmethod
+    def _copy(self, f: tuple[str | os.PathLike, Iterable[str | os.PathLike]]):
+        # it's a tuple with path to install to and a list of files
+        dir = convert_path(f[0])
+        if not os.path.isabs(dir):
+            dir = os.path.join(self.install_dir, dir)
+        elif self.root:
+            dir = change_root(self.root, dir)
+        self.mkpath(dir)
+
+        if f[1] == []:
+            # If there are no files listed, the user must be
+            # trying to create an empty directory, so add the
+            # directory to the list of output files.
+            self.outfiles.append(dir)
+        else:
+            # Copy files, adding them to the list of output files.
+            for data in f[1]:
+                data = convert_path(data)
+                (out, _) = self.copy_file(data, dir)
                 self.outfiles.append(out)
-            else:
-                # it's a tuple with path to install to and a list of files
-                dir = convert_path(f[0])
-                if not os.path.isabs(dir):
-                    dir = os.path.join(self.install_dir, dir)
-                elif self.root:
-                    dir = change_root(self.root, dir)
-                self.mkpath(dir)
-
-                if f[1] == []:
-                    # If there are no files listed, the user must be
-                    # trying to create an empty directory, so add the
-                    # directory to the list of output files.
-                    self.outfiles.append(dir)
-                else:
-                    # Copy files, adding them to the list of output files.
-                    for data in f[1]:
-                        data = convert_path(data)
-                        (out, _) = self.copy_file(data, dir)
-                        self.outfiles.append(out)
+
+    @_copy.register(str)
+    @_copy.register(os.PathLike)
+    def _(self, f: str | os.PathLike):
+        # it's a simple file, so copy it
+        f = convert_path(f)
+        if self.warn_dir:
+            self.warn(
+                "setup script did not provide a directory for "
+                f"'{f}' -- installing right in '{self.install_dir}'"
+            )
+        (out, _) = self.copy_file(f, self.install_dir)
+        self.outfiles.append(out)
 
     def get_inputs(self):
         return self.data_files or []
diff --git a/distutils/tests/test_install_data.py b/distutils/tests/test_install_data.py
index f34070b1..4b15a269 100644
--- a/distutils/tests/test_install_data.py
+++ b/distutils/tests/test_install_data.py
@@ -1,11 +1,13 @@
 """Tests for distutils.command.install_data."""
 
 import os
-from distutils.command.install_data import install_data
-from distutils.tests import support
+import pathlib
 
 import pytest
 
+from distutils.command.install_data import install_data
+from distutils.tests import support
+
 
 @pytest.mark.usefixtures('save_env')
 class TestInstallData(
@@ -18,22 +20,27 @@ def test_simple_run(self):
 
         # data_files can contain
         #  - simple files
+        #  - a Path object
         #  - a tuple with a path, and a list of file
         one = os.path.join(pkg_dir, 'one')
         self.write_file(one, 'xxx')
         inst2 = os.path.join(pkg_dir, 'inst2')
         two = os.path.join(pkg_dir, 'two')
         self.write_file(two, 'xxx')
+        three = pathlib.Path(pkg_dir) / 'three'
+        self.write_file(three, 'xxx')
 
-        cmd.data_files = [one, (inst2, [two])]
-        assert cmd.get_inputs() == [one, (inst2, [two])]
+        cmd.data_files = [one, (inst2, [two]), three]
+        assert cmd.get_inputs() == [one, (inst2, [two]), three]
 
         # let's run the command
         cmd.ensure_finalized()
         cmd.run()
 
         # let's check the result
-        assert len(cmd.get_outputs()) == 2
+        assert len(cmd.get_outputs()) == 3
+        rthree = os.path.split(one)[-1]
+        assert os.path.exists(os.path.join(inst, rthree))
         rtwo = os.path.split(two)[-1]
         assert os.path.exists(os.path.join(inst2, rtwo))
         rone = os.path.split(one)[-1]
@@ -46,21 +53,23 @@ def test_simple_run(self):
         cmd.run()
 
         # let's check the result
-        assert len(cmd.get_outputs()) == 2
+        assert len(cmd.get_outputs()) == 3
+        assert os.path.exists(os.path.join(inst, rthree))
         assert os.path.exists(os.path.join(inst2, rtwo))
         assert os.path.exists(os.path.join(inst, rone))
         cmd.outfiles = []
 
         # now using root and empty dir
         cmd.root = os.path.join(pkg_dir, 'root')
-        inst4 = os.path.join(pkg_dir, 'inst4')
-        three = os.path.join(cmd.install_dir, 'three')
-        self.write_file(three, 'xx')
-        cmd.data_files = [one, (inst2, [two]), ('inst3', [three]), (inst4, [])]
+        inst5 = os.path.join(pkg_dir, 'inst5')
+        four = os.path.join(cmd.install_dir, 'four')
+        self.write_file(four, 'xx')
+        cmd.data_files = [one, (inst2, [two]), three, ('inst5', [four]), (inst5, [])]
         cmd.ensure_finalized()
         cmd.run()
 
         # let's check the result
-        assert len(cmd.get_outputs()) == 4
+        assert len(cmd.get_outputs()) == 5
+        assert os.path.exists(os.path.join(inst, rthree))
         assert os.path.exists(os.path.join(inst2, rtwo))
         assert os.path.exists(os.path.join(inst, rone))
diff --git a/distutils/tests/test_util.py b/distutils/tests/test_util.py
index 0de4e1a5..00c9743e 100644
--- a/distutils/tests/test_util.py
+++ b/distutils/tests/test_util.py
@@ -5,6 +5,7 @@
 import email.policy
 import io
 import os
+import pathlib
 import sys
 import sysconfig as stdlib_sysconfig
 import unittest.mock as mock
@@ -63,30 +64,9 @@ def test_get_platform(self):
                 assert get_platform() == 'win-arm64'
 
     def test_convert_path(self):
-        # linux/mac
-        os.sep = '/'
-
-        def _join(path):
-            return '/'.join(path)
-
-        os.path.join = _join
-
-        assert convert_path('/home/to/my/stuff') == '/home/to/my/stuff'
-
-        # win
-        os.sep = '\\'
-
-        def _join(*path):
-            return '\\'.join(path)
-
-        os.path.join = _join
-
-        with pytest.raises(ValueError):
-            convert_path('/home/to/my/stuff')
-        with pytest.raises(ValueError):
-            convert_path('home/to/my/stuff/')
-
-        assert convert_path('home/to/my/stuff') == 'home\\to\\my\\stuff'
+        expected = os.sep.join(('', 'home', 'to', 'my', 'stuff'))
+        assert convert_path('/home/to/my/stuff') == expected
+        assert convert_path(pathlib.Path('/home/to/my/stuff')) == expected
         assert convert_path('.') == os.curdir
 
     def test_change_root(self):
diff --git a/distutils/util.py b/distutils/util.py
index 9db89b09..4cc6bd28 100644
--- a/distutils/util.py
+++ b/distutils/util.py
@@ -4,9 +4,12 @@
 one of the other *util.py modules.
 """
 
+from __future__ import annotations
+
 import functools
 import importlib.util
 import os
+import pathlib
 import re
 import string
 import subprocess
@@ -14,6 +17,7 @@
 import sysconfig
 import tempfile
 
+from ._functools import pass_none
 from ._log import log
 from ._modified import newer
 from .errors import DistutilsByteCompileError, DistutilsPlatformError
@@ -116,33 +120,23 @@ def split_version(s):
     return [int(n) for n in s.split('.')]
 
 
-def convert_path(pathname):
-    """Return 'pathname' as a name that will work on the native filesystem,
-    i.e. split it on '/' and put it back together again using the current
-    directory separator.  Needed because filenames in the setup script are
-    always supplied in Unix style, and have to be converted to the local
-    convention before we can actually use them in the filesystem.  Raises
-    ValueError on non-Unix-ish systems if 'pathname' either starts or
-    ends with a slash.
+@pass_none
+def convert_path(pathname: str | os.PathLike) -> str:
+    r"""
+    Allow for pathlib.Path inputs, coax to a native path string.
+
+    If None is passed, will just pass it through as
+    Setuptools relies on this behavior.
+
+    >>> convert_path(None) is None
+    True
+
+    Removes empty paths.
+
+    >>> convert_path('foo/./bar').replace('\\', '/')
+    'foo/bar'
     """
-    if os.sep == '/':
-        return pathname
-    if not pathname:
-        return pathname
-    if pathname[0] == '/':
-        raise ValueError(f"path '{pathname}' cannot be absolute")
-    if pathname[-1] == '/':
-        raise ValueError(f"path '{pathname}' cannot end with '/'")
-
-    paths = pathname.split('/')
-    while '.' in paths:
-        paths.remove('.')
-    if not paths:
-        return os.curdir
-    return os.path.join(*paths)
-
-
-# convert_path ()
+    return os.fspath(pathlib.PurePath(pathname))
 
 
 def change_root(new_root, pathname):