diff --git a/mkdocs/nav.py b/mkdocs/nav.py
index c8257e12..932399b4 100644
--- a/mkdocs/nav.py
+++ b/mkdocs/nav.py
@@ -209,14 +209,17 @@ def _generate_site_navigation(pages_config, url_context, use_directory_urls=True
             )
             raise exceptions.ConfigurationError(msg)
 
+        # If both the title and child_title are None, then we
+        # have just been given a path. If that path contains a /
+        # then lets automatically nest it.
+        if title is None and child_title is None and os.path.sep in path:
+            filename = path.split(os.path.sep)[-1]
+            child_title = filename_to_title(filename)
+
         if title is None:
             filename = path.split(os.path.sep)[0]
             title = filename_to_title(filename)
 
-        if child_title is None and os.path.sep in path:
-            filename = path.split(os.path.sep)[-1]
-            child_title = filename_to_title(filename)
-
         url = utils.get_url_path(path, use_directory_urls)
 
         if not child_title:

Title is used as a section if file is in subdirectory
Assuming I have a file at `research/stats.md` and a config line:

```
pages:
- ["research/stats.md", "Stats about Our Collection"]
```

I would assume that it would generate a top-level nav item titled  "Stats about Our Collection".

In reality, it generates a section **Stats about Our Collection** with a sub-item titled **stats**.

I'm 90% sure this has to do with the logic in [nav.py](https://github.com/mkdocs/mkdocs/blob/master/mkdocs/nav.py#L212-L218) around `child_titles`.




diff --git a/mkdocs/tests/nav_tests.py b/mkdocs/tests/nav_tests.py
index 7013a66e..b6876f35 100644
--- a/mkdocs/tests/nav_tests.py
+++ b/mkdocs/tests/nav_tests.py
@@ -63,6 +63,39 @@ class SiteNavigationTests(unittest.TestCase):
         self.assertEqual(len(site_navigation.nav_items), 3)
         self.assertEqual(len(site_navigation.pages), 6)
 
+    def test_nested_ungrouped(self):
+        pages = [
+            ('index.md', 'Home'),
+            ('about/contact.md', 'Contact'),
+            ('about/sub/license.md', 'License Title')
+        ]
+        expected = dedent("""
+        Home - /
+        Contact - /about/contact/
+        License Title - /about/sub/license/
+        """)
+        site_navigation = nav.SiteNavigation(pages)
+        self.assertEqual(str(site_navigation).strip(), expected)
+        self.assertEqual(len(site_navigation.nav_items), 3)
+        self.assertEqual(len(site_navigation.pages), 3)
+
+    def test_nested_ungrouped_no_titles(self):
+        pages = [
+            ('index.md',),
+            ('about/contact.md'),
+            ('about/sub/license.md')
+        ]
+        expected = dedent("""
+        Home - /
+        About
+            Contact - /about/contact/
+            License - /about/sub/license/
+        """)
+        site_navigation = nav.SiteNavigation(pages)
+        self.assertEqual(str(site_navigation).strip(), expected)
+        self.assertEqual(len(site_navigation.nav_items), 2)
+        self.assertEqual(len(site_navigation.pages), 3)
+
     def test_walk_simple_toc(self):
         pages = [
             ('index.md', 'Home'),

pip install -e .
parse_log_pytest
requirements.txt
nose mock pytest
pip install tox
3.4
requirements.txt
pytest --no-header -rA --tb=line --color=no -p no:cacheprovider -W ignore::DeprecationWarning
attrs==22.2.0
certifi==2021.5.30
distlib==0.3.9
filelock==3.4.1
ghp-import==2.1.0
importlib-metadata==4.8.3
importlib-resources==5.4.0
iniconfig==1.1.1
Jinja2==3.0.3
Markdown==2.4.1
MarkupSafe==2.0.1
-e git+https://github.com/mkdocs/mkdocs.git@88bb485ee4bd863f1cbfed6a786ef995cc844929#egg=mkdocs
mock==5.2.0
nose==1.3.7
packaging==21.3
platformdirs==2.4.0
pluggy==1.0.0
py==1.11.0
pyparsing==3.1.4
pytest==7.0.1
python-dateutil==2.9.0.post0
PyYAML==6.0.1
six==1.17.0
toml==0.10.2
tomli==1.2.3
tox==3.28.0
typing_extensions==4.1.1
virtualenv==20.17.1
watchdog==2.3.1
zipp==3.6.0

name: mkdocs
channels:
  - defaults
  - https://repo.anaconda.com/pkgs/main
  - https://repo.anaconda.com/pkgs/r
  - conda-forge
dependencies:
  - _libgcc_mutex=0.1=main
  - _openmp_mutex=5.1=1_gnu
  - ca-certificates=2025.2.25=h06a4308_0
  - certifi=2021.5.30=py36h06a4308_0
  - ld_impl_linux-64=2.40=h12ee557_0
  - libffi=3.3=he6710b0_2
  - libgcc-ng=11.2.0=h1234567_1
  - libgomp=11.2.0=h1234567_1
  - libstdcxx-ng=11.2.0=h1234567_1
  - ncurses=6.4=h6a678d5_0
  - openssl=1.1.1w=h7f8727e_0
  - pip=21.2.2=py36h06a4308_0
  - python=3.6.13=h12debd9_1
  - readline=8.2=h5eee18b_0
  - setuptools=58.0.4=py36h06a4308_0
  - sqlite=3.45.3=h5eee18b_0
  - tk=8.6.14=h39e8969_0
  - wheel=0.37.1=pyhd3eb1b0_0
  - xz=5.6.4=h5eee18b_1
  - zlib=1.2.13=h5eee18b_1
  - pip:
      - attrs==22.2.0
      - distlib==0.3.9
      - filelock==3.4.1
      - ghp-import==2.1.0
      - importlib-metadata==4.8.3
      - importlib-resources==5.4.0
      - iniconfig==1.1.1
      - jinja2==3.0.3
      - markdown==2.4.1
      - markupsafe==2.0.1
      - mock==5.2.0
      - nose==1.3.7
      - packaging==21.3
      - platformdirs==2.4.0
      - pluggy==1.0.0
      - py==1.11.0
      - pyparsing==3.1.4
      - pytest==7.0.1
      - python-dateutil==2.9.0.post0
      - pyyaml==6.0.1
      - six==1.17.0
      - toml==0.10.2
      - tomli==1.2.3
      - tox==3.28.0
      - typing-extensions==4.1.1
      - virtualenv==20.17.1
      - watchdog==2.3.1
      - zipp==3.6.0
prefix: /opt/conda/envs/mkdocs

mkdocs/tests/nav_tests.py::SiteNavigationTests::test_nested_ungrouped
mkdocs/tests/nav_tests.py::SiteNavigationTests::test_base_url mkdocs/tests/nav_tests.py::SiteNavigationTests::test_empty_toc_item mkdocs/tests/nav_tests.py::SiteNavigationTests::test_generate_site_navigation mkdocs/tests/nav_tests.py::SiteNavigationTests::test_generate_site_navigation_windows mkdocs/tests/nav_tests.py::SiteNavigationTests::test_indented_toc mkdocs/tests/nav_tests.py::SiteNavigationTests::test_invalid_pages_config mkdocs/tests/nav_tests.py::SiteNavigationTests::test_nested_ungrouped_no_titles mkdocs/tests/nav_tests.py::SiteNavigationTests::test_relative_md_links_have_slash mkdocs/tests/nav_tests.py::SiteNavigationTests::test_simple_toc mkdocs/tests/nav_tests.py::SiteNavigationTests::test_walk_empty_toc mkdocs/tests/nav_tests.py::SiteNavigationTests::test_walk_indented_toc mkdocs/tests/nav_tests.py::SiteNavigationTests::test_walk_simple_toc
mkdocs/nav.py
mkdocs/nav.py