diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 834a1ad3..f484089a 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -147,6 +147,7 @@ jobs:
       - uses: msys2/setup-msys2@v2
         with:
           msystem: ${{matrix.sys}}
+          update: true
           install: |
             mingw-w64-${{matrix.env}}-toolchain
             mingw-w64-${{matrix.env}}-python
diff --git a/distutils/tests/test_filelist.py b/distutils/tests/test_filelist.py
index 130e6fb5..765b0a89 100644
--- a/distutils/tests/test_filelist.py
+++ b/distutils/tests/test_filelist.py
@@ -3,6 +3,7 @@
 import logging
 import os
 import re
+import sys
 from distutils import debug, filelist
 from distutils.errors import DistutilsTemplateError
 from distutils.filelist import FileList, glob_to_re, translate_pattern
@@ -49,18 +50,21 @@ def test_glob_to_re(self):
         if os.sep == '\\':
             sep = re.escape(os.sep)
 
+        # https://docs.python.org/3/whatsnew/3.14.html#re
+        end = r"\z" if sys.version_info >= (3, 14) else r"\Z"
+
         for glob, regex in (
             # simple cases
-            ('foo*', r'(?s:foo[^%(sep)s]*)\Z'),
-            ('foo?', r'(?s:foo[^%(sep)s])\Z'),
-            ('foo??', r'(?s:foo[^%(sep)s][^%(sep)s])\Z'),
+            ('foo*', r'(?s:foo[^%(sep)s]*)%(end)s'),
+            ('foo?', r'(?s:foo[^%(sep)s])%(end)s'),
+            ('foo??', r'(?s:foo[^%(sep)s][^%(sep)s])%(end)s'),
             # special cases
-            (r'foo\\*', r'(?s:foo\\\\[^%(sep)s]*)\Z'),
-            (r'foo\\\*', r'(?s:foo\\\\\\[^%(sep)s]*)\Z'),
-            ('foo????', r'(?s:foo[^%(sep)s][^%(sep)s][^%(sep)s][^%(sep)s])\Z'),
-            (r'foo\\??', r'(?s:foo\\\\[^%(sep)s][^%(sep)s])\Z'),
+            (r'foo\\*', r'(?s:foo\\\\[^%(sep)s]*)%(end)s'),
+            (r'foo\\\*', r'(?s:foo\\\\\\[^%(sep)s]*)%(end)s'),
+            ('foo????', r'(?s:foo[^%(sep)s][^%(sep)s][^%(sep)s][^%(sep)s])%(end)s'),
+            (r'foo\\??', r'(?s:foo\\\\[^%(sep)s][^%(sep)s])%(end)s'),
         ):
-            regex = regex % {'sep': sep}
+            regex = regex % {'sep': sep, 'end': end}
             assert glob_to_re(glob) == regex
 
     def test_process_template_line(self):
diff --git a/distutils/tests/test_util.py b/distutils/tests/test_util.py
index 00c9743e..c053a153 100644
--- a/distutils/tests/test_util.py
+++ b/distutils/tests/test_util.py
@@ -20,6 +20,7 @@
     get_host_platform,
     get_platform,
     grok_environment_error,
+    is_mingw,
     rfc822_escape,
     split_quoted,
     strtobool,
@@ -42,6 +43,7 @@ def environment(monkeypatch):
 
 @pytest.mark.usefixtures('save_env')
 class TestUtil:
+    @pytest.mark.skipif(is_mingw(), reason="mingw has non-standard platform names")
     def test_get_host_platform(self):
         with mock.patch('os.name', 'nt'):
             with mock.patch('sys.version', '... [... (ARM64)]'):
diff --git a/pyproject.toml b/pyproject.toml
index f26f750c..3183143a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -67,6 +67,7 @@ doc = [
 check = [
 	"pytest-checkdocs >= 2.4",
 	"pytest-ruff >= 0.2.1; sys_platform != 'cygwin'",
+	"ruff == 0.13.3; sys_platform != 'cygwin'",
 ]
 
 cover = [
@@ -80,6 +81,7 @@ enabler = [
 type = [
 	# upstream
 	"pytest-mypy",
+	"mypy == 1.15.0",
 
 	# local
 	"types-docutils",