diff --git a/scripts/check_headers.py b/scripts/check_headers.py
index f1f19a14..1ff69fcb 100755
--- a/scripts/check_headers.py
+++ b/scripts/check_headers.py
@@ -52,8 +52,8 @@
 
 def get_file_header(filename):
     """Read the file header from the file."""
-    with open(filename, 'rt') as f:
-        # Only read the first 2048 bytes to avoid loading too much and the
+    with open(filename, 'rt', encoding='utf-8') as f:
+        # Only read the first 2048 characters to avoid loading too much and the
         # license information should be in the first part anyway.
         return f.read(2048)
 
@@ -74,7 +74,8 @@ def get_file_header(filename):
     for filename in sorted(files_to_check):
         contents = get_file_header(filename)
         m = identification_re.match(contents)
-        if not bool(m) or m.group('filename') not in (filename, os.path.basename(filename)):
+        if not bool(m) or m.group('filename') not in (
+                filename, filename.replace(os.sep, '/'), os.path.basename(filename)):
             print('%s: Incorrect file identification' % filename)
             fail = True
         if not bool(license_re.search(contents)):
diff --git a/tests/test_check_headers.py b/tests/test_check_headers.py
new file mode 100644
index 00000000..295bd73a
--- /dev/null
+++ b/tests/test_check_headers.py
@@ -0,0 +1,108 @@
+# test_check_headers.py - tests for the source-header checker
+#
+# Copyright (C) 2026 Ryan Duguid
+#
+# This library is free software; you can redistribute it and/or
+# modify it under the terms of the GNU Lesser General Public
+# License as published by the Free Software Foundation; either
+# version 2.1 of the License, or (at your option) any later version.
+#
+# This library is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the GNU
+# Lesser General Public License for more details.
+#
+# You should have received a copy of the GNU Lesser General Public
+# License along with this library; if not, see <https://www.gnu.org/licenses/>.
+
+"""Tests for the standalone source-header checker."""
+
+from __future__ import annotations
+
+import os
+import subprocess
+import sys
+import tempfile
+import unittest
+from pathlib import Path
+
+
+class TestHeaders(unittest.TestCase):
+    """Exercise header validation through the script's command-line interface."""
+
+    def setUp(self) -> None:
+        """Read the standard licence header without importing the script."""
+        self.checker = Path(__file__).resolve().parents[1] / 'scripts' / 'check_headers.py'
+        self.header = self.checker.read_text(encoding='utf-8').split('"""', 1)[0]
+        self.assertIn('# check_headers.py - ', self.header)
+
+    def _check(self, filename: str, contents: str) -> subprocess.CompletedProcess[str]:
+        """Run the checker against one fixture in an isolated directory."""
+        # The checker uses only the standard library, so skip site startup hooks.
+        command = [sys.executable, '-S']
+        if os.name == 'nt':
+            # Disable UTF-8 mode so it cannot hide the locale-decoding failure.
+            command.extend(['-X', 'utf8=0'])
+        command.append(str(self.checker))
+        with tempfile.TemporaryDirectory() as directory:
+            fixture = Path(directory) / filename
+            fixture.parent.mkdir(parents=True, exist_ok=True)
+            fixture.write_text(contents, encoding='utf-8')
+            return subprocess.run(command, cwd=directory, capture_output=True, text=True, encoding='utf-8', check=False)
+
+    def test_utf8_header(self) -> None:
+        """Read a UTF-8 quote whose final byte is undefined in cp1252."""
+        header = self.header.replace('# check_headers.py - ', '# check_headers.py - \u201d ', 1)
+        result = self._check('check_headers.py', header)
+        self.assertEqual((result.returncode, result.stdout, result.stderr), (0, '', ''))
+
+    def test_relative_path(self) -> None:
+        """Accept the portable relative filename used by updater headings."""
+        header = self.header.replace('# check_headers.py - ', '# update/check_headers.py - ', 1)
+        result = self._check('update/check_headers.py', header)
+        self.assertEqual((result.returncode, result.stdout, result.stderr), (0, '', ''))
+
+    def test_native_path(self) -> None:
+        """Preserve acceptance of an exact native relative filename."""
+        native = str(Path('update') / 'check_headers.py')
+        header = self.header.replace('# check_headers.py - ', '# %s - ' % native, 1)
+        result = self._check('update/check_headers.py', header)
+        self.assertEqual((result.returncode, result.stdout, result.stderr), (0, '', ''))
+
+    def test_basename(self) -> None:
+        """Preserve acceptance of a basename in a nested file."""
+        result = self._check('update/check_headers.py', self.header)
+        self.assertEqual((result.returncode, result.stdout, result.stderr), (0, '', ''))
+
+    def test_wrong_identification(self) -> None:
+        """Reject a wrong filename and a wrong directory with the same basename."""
+        for name in ('other.py', 'other/check_headers.py'):
+            with self.subTest(name=name):
+                header = self.header.replace('# check_headers.py - ', '# %s - ' % name, 1)
+                result = self._check('update/check_headers.py', header)
+                expected = '%s: Incorrect file identification\n' % str(Path('update') / 'check_headers.py')
+                self.assertEqual((result.returncode, result.stdout, result.stderr), (1, expected, ''))
+
+    def test_missing_identification(self) -> None:
+        """Reject a missing identification without raising an exception."""
+        header = self.header.replace('# check_headers.py - ', '# ', 1)
+        result = self._check('check_headers.py', header)
+        self.assertEqual(
+            (result.returncode, result.stdout, result.stderr),
+            (1, 'check_headers.py: Incorrect file identification\n', ''))
+
+    def test_wrong_licence(self) -> None:
+        """Reject missing and materially altered licence text."""
+        for header in (self.header.split('# This library', 1)[0], self.header.replace('version 2.1', 'version 3.0')):
+            with self.subTest(header=header):
+                result = self._check('check_headers.py', header)
+                self.assertEqual(
+                    (result.returncode, result.stdout, result.stderr),
+                    (1, 'check_headers.py: Incorrect license text\n', ''))
+
+    def test_both_errors(self) -> None:
+        """Report identification and licence errors in their existing order."""
+        result = self._check('other.py', self.header.replace('version 2.1', 'version 3.0'))
+        self.assertEqual(
+            (result.returncode, result.stdout, result.stderr),
+            (1, 'other.py: Incorrect file identification\nother.py: Incorrect license text\n', ''))