diff --git a/mkdocs/tests/structure/file_tests.py b/mkdocs/tests/structure/file_tests.py
index 1c301cb5..200efd73 100644
--- a/mkdocs/tests/structure/file_tests.py
+++ b/mkdocs/tests/structure/file_tests.py
@@ -79,256 +79,167 @@ class TestFiles(PathAssertionMixin, unittest.TestCase):
         )
 
     def test_md_file(self):
-        f = File('foo.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo.md')
-        self.assertEqual(f.dest_uri, 'foo.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo.html')
-        self.assertEqual(f.url, 'foo.html')
-        self.assertEqual(f.name, 'foo')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_md_file_use_directory_urls(self):
-        f = File('foo.md', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo.md')
-        self.assertEqual(f.dest_uri, 'foo/index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/index.html')
-        self.assertEqual(f.url, 'foo/')
-        self.assertEqual(f.name, 'foo')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo.md', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo.md')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo.md')
+                if use_directory_urls:
+                    self.assertEqual(f.dest_uri, 'foo/index.html')
+                    self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/index.html')
+                    self.assertEqual(f.url, 'foo/')
+                else:
+                    self.assertEqual(f.dest_uri, 'foo.html')
+                    self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo.html')
+                    self.assertEqual(f.url, 'foo.html')
+                self.assertEqual(f.name, 'foo')
+                self.assertTrue(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_md_file_nested(self):
-        f = File('foo/bar.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/bar.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.md')
-        self.assertEqual(f.dest_uri, 'foo/bar.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.html')
-        self.assertEqual(f.url, 'foo/bar.html')
-        self.assertEqual(f.name, 'bar')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_md_file_nested_use_directory_urls(self):
-        f = File('foo/bar.md', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/bar.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.md')
-        self.assertEqual(f.dest_uri, 'foo/bar/index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar/index.html')
-        self.assertEqual(f.url, 'foo/bar/')
-        self.assertEqual(f.name, 'bar')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/bar.md', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/bar.md')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.md')
+                if use_directory_urls:
+                    self.assertEqual(f.dest_uri, 'foo/bar/index.html')
+                    self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar/index.html')
+                    self.assertEqual(f.url, 'foo/bar/')
+                else:
+                    self.assertEqual(f.dest_uri, 'foo/bar.html')
+                    self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.html')
+                    self.assertEqual(f.url, 'foo/bar.html')
+                self.assertEqual(f.name, 'bar')
+                self.assertTrue(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_md_index_file(self):
-        f = File('index.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'index.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/index.md')
-        self.assertEqual(f.dest_uri, 'index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
-        self.assertEqual(f.url, 'index.html')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('index.md', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'index.md')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/index.md')
+                self.assertEqual(f.dest_uri, 'index.html')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
+                if use_directory_urls:
+                    self.assertEqual(f.url, './')
+                else:
+                    self.assertEqual(f.url, 'index.html')
+                self.assertEqual(f.name, 'index')
+                self.assertTrue(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_md_readme_index_file(self):
-        f = File('README.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'README.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/README.md')
-        self.assertEqual(f.dest_uri, 'index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
-        self.assertEqual(f.url, 'index.html')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_md_index_file_use_directory_urls(self):
-        f = File('index.md', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'index.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/index.md')
-        self.assertEqual(f.dest_uri, 'index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
-        self.assertEqual(f.url, './')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_md_readme_index_file_use_directory_urls(self):
-        f = File('README.md', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'README.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/README.md')
-        self.assertEqual(f.dest_uri, 'index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
-        self.assertEqual(f.url, './')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('README.md', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'README.md')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/README.md')
+                self.assertEqual(f.dest_uri, 'index.html')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/index.html')
+                if use_directory_urls:
+                    self.assertEqual(f.url, './')
+                else:
+                    self.assertEqual(f.url, 'index.html')
+                self.assertEqual(f.name, 'index')
+                self.assertTrue(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_md_index_file_nested(self):
-        f = File('foo/index.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/index.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/index.md')
-        self.assertEqual(f.dest_uri, 'foo/index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/index.html')
-        self.assertEqual(f.url, 'foo/index.html')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_md_index_file_nested_use_directory_urls(self):
-        f = File('foo/index.md', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/index.md')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/index.md')
-        self.assertEqual(f.dest_uri, 'foo/index.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/index.html')
-        self.assertEqual(f.url, 'foo/')
-        self.assertEqual(f.name, 'index')
-        self.assertTrue(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/index.md', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/index.md')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/index.md')
+                self.assertEqual(f.dest_uri, 'foo/index.html')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/index.html')
+                if use_directory_urls:
+                    self.assertEqual(f.url, 'foo/')
+                else:
+                    self.assertEqual(f.url, 'foo/index.html')
+                self.assertEqual(f.name, 'index')
+                self.assertTrue(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_static_file(self):
-        f = File('foo/bar.html', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/bar.html')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.html')
-        self.assertEqual(f.dest_uri, 'foo/bar.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.html')
-        self.assertEqual(f.url, 'foo/bar.html')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertTrue(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_static_file_use_directory_urls(self):
-        f = File('foo/bar.html', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/bar.html')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.html')
-        self.assertEqual(f.dest_uri, 'foo/bar.html')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.html')
-        self.assertEqual(f.url, 'foo/bar.html')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertTrue(f.is_static_page())
-        self.assertFalse(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/bar.html', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/bar.html')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.html')
+                self.assertEqual(f.dest_uri, 'foo/bar.html')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.html')
+                self.assertEqual(f.url, 'foo/bar.html')
+                self.assertEqual(f.name, 'bar')
+                self.assertFalse(f.is_documentation_page())
+                self.assertTrue(f.is_static_page())
+                self.assertFalse(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_media_file(self):
-        f = File('foo/bar.jpg', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/bar.jpg')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.jpg')
-        self.assertEqual(f.dest_uri, 'foo/bar.jpg')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.jpg')
-        self.assertEqual(f.url, 'foo/bar.jpg')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_media_file_use_directory_urls(self):
-        f = File('foo/bar.jpg', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/bar.jpg')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.jpg')
-        self.assertEqual(f.dest_uri, 'foo/bar.jpg')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.jpg')
-        self.assertEqual(f.url, 'foo/bar.jpg')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/bar.jpg', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/bar.jpg')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.jpg')
+                self.assertEqual(f.dest_uri, 'foo/bar.jpg')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.jpg')
+                self.assertEqual(f.url, 'foo/bar.jpg')
+                self.assertEqual(f.name, 'bar')
+                self.assertFalse(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertTrue(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_javascript_file(self):
-        f = File('foo/bar.js', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/bar.js')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.js')
-        self.assertEqual(f.dest_uri, 'foo/bar.js')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.js')
-        self.assertEqual(f.url, 'foo/bar.js')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertTrue(f.is_javascript())
-        self.assertFalse(f.is_css())
-
-    def test_javascript_file_use_directory_urls(self):
-        f = File('foo/bar.js', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/bar.js')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.js')
-        self.assertEqual(f.dest_uri, 'foo/bar.js')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.js')
-        self.assertEqual(f.url, 'foo/bar.js')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertTrue(f.is_javascript())
-        self.assertFalse(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/bar.js', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/bar.js')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.js')
+                self.assertEqual(f.dest_uri, 'foo/bar.js')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.js')
+                self.assertEqual(f.url, 'foo/bar.js')
+                self.assertEqual(f.name, 'bar')
+                self.assertFalse(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertTrue(f.is_media_file())
+                self.assertTrue(f.is_javascript())
+                self.assertFalse(f.is_css())
 
     def test_css_file(self):
-        f = File('foo/bar.css', '/path/to/docs', '/path/to/site', use_directory_urls=False)
-        self.assertEqual(f.src_uri, 'foo/bar.css')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.css')
-        self.assertEqual(f.dest_uri, 'foo/bar.css')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.css')
-        self.assertEqual(f.url, 'foo/bar.css')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertTrue(f.is_css())
-
-    def test_css_file_use_directory_urls(self):
-        f = File('foo/bar.css', '/path/to/docs', '/path/to/site', use_directory_urls=True)
-        self.assertEqual(f.src_uri, 'foo/bar.css')
-        self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.css')
-        self.assertEqual(f.dest_uri, 'foo/bar.css')
-        self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.css')
-        self.assertEqual(f.url, 'foo/bar.css')
-        self.assertEqual(f.name, 'bar')
-        self.assertFalse(f.is_documentation_page())
-        self.assertFalse(f.is_static_page())
-        self.assertTrue(f.is_media_file())
-        self.assertFalse(f.is_javascript())
-        self.assertTrue(f.is_css())
+        for use_directory_urls in True, False:
+            with self.subTest(use_directory_urls=use_directory_urls):
+                f = File('foo/bar.css', '/path/to/docs', '/path/to/site', use_directory_urls)
+                self.assertEqual(f.src_uri, 'foo/bar.css')
+                self.assertPathsEqual(f.abs_src_path, '/path/to/docs/foo/bar.css')
+                self.assertEqual(f.dest_uri, 'foo/bar.css')
+                self.assertPathsEqual(f.abs_dest_path, '/path/to/site/foo/bar.css')
+                self.assertEqual(f.url, 'foo/bar.css')
+                self.assertEqual(f.name, 'bar')
+                self.assertFalse(f.is_documentation_page())
+                self.assertFalse(f.is_static_page())
+                self.assertTrue(f.is_media_file())
+                self.assertFalse(f.is_javascript())
+                self.assertTrue(f.is_css())
 
     def test_file_name_with_space(self):
         f = File('foo bar.md', '/path/to/docs', '/path/to/site', use_directory_urls=False)