diff --git a/.github/workflows/windows.yml b/.github/workflows/windows.yml
new file mode 100644
index 00000000000000..235b5b86a437be
--- /dev/null
+++ b/.github/workflows/windows.yml
@@ -0,0 +1,28 @@
+name: Manual Windows
+
+on:
+  workflow_dispatch:
+    inputs:
+      arch:
+        description: CPU architecture
+        required: true
+        type: choice
+        options:
+          - x86
+          - x64
+          - arm64
+      free-threading:
+        description: Whether to compile CPython in free-threading mode
+        required: false
+        type: boolean
+        default: false
+
+env:
+  FORCE_COLOR: 1
+
+jobs:
+  build-windows:
+    uses: ./.github/workflows/reusable-windows.yml
+    with:
+      arch: ${{ inputs.arch }}
+      free-threading: ${{ inputs.free-threading }}
diff --git a/Lib/test/test_cmd_line.py b/Lib/test/test_cmd_line.py
index 1b40e0d05fe3bc..92c050cb5d2c2a 100644
--- a/Lib/test/test_cmd_line.py
+++ b/Lib/test/test_cmd_line.py
@@ -970,12 +970,22 @@ def test_python_legacy_windows_fs_encoding(self):
         rc, out, err = assert_python_ok('-c', code, PYTHONLEGACYWINDOWSFSENCODING='1')
         self.assertIn(expected.encode(), out)
 
-    @unittest.skipUnless(support.MS_WINDOWS, 'Test only applicable on Windows')
+    @unittest.skipUnless(type(sys.stderr.buffer.raw).__name__ == "_WindowsConsoleIO",
+                         "Test only applicable on Windows with console IO")
     def test_python_legacy_windows_stdio(self):
-        code = "import sys; print(sys.stdin.encoding, sys.stdout.encoding)"
-        expected = 'cp'
-        rc, out, err = assert_python_ok('-c', code, PYTHONLEGACYWINDOWSSTDIO='1')
-        self.assertIn(expected.encode(), out)
+        def get_stderr_class(legacy_windows_stdio):
+            code = 'import sys; print(type(sys.stderr.buffer.raw))'
+            env = {'PYTHONLEGACYWINDOWSSTDIO': str(int(legacy_windows_stdio))}
+            # use stderr=None as legacy_windows_stdio doesn't affect pipes
+            p = spawn_python('-c', code, env=env, stderr=None)
+            out = kill_python(p).strip().decode('ascii', 'ignore')
+            return out.removeprefix("<class '").removesuffix("'>")
+
+        out = get_stderr_class(legacy_windows_stdio=True)
+        self.assertEqual('_io.FileIO', out)
+
+        out = get_stderr_class(legacy_windows_stdio=False)
+        self.assertEqual('_io._WindowsConsoleIO', out)
 
     @unittest.skipIf("-fsanitize" in sysconfig.get_config_vars().get('PY_CFLAGS', ()),
                      "PYTHONMALLOCSTATS doesn't work with ASAN")