diff --git a/awx/main/middleware.py b/awx/main/middleware.py
index d485ce45f7e3..433ade596fe4 100644
--- a/awx/main/middleware.py
+++ b/awx/main/middleware.py
@@ -6,7 +6,7 @@
 import threading
 import time
 import urllib.parse
-from pathlib import Path
+from pathlib import Path, PurePosixPath
 
 from django.conf import settings
 from django.contrib.auth import logout
@@ -138,14 +138,36 @@ def _named_url_to_pk(cls, node, resource, named_url):
 
     @classmethod
     def _convert_named_url(cls, url_path):
-        url_units = url_path.split('/')
-        # If the identifier is an empty string, it is always invalid.
-        if len(url_units) < 6 or url_units[1] != 'api' or url_units[2] not in ['v2'] or not url_units[4]:
-            return url_path
-        resource = url_units[3]
+        default_prefix = PurePosixPath('/api/v2/')
+        optional_prefix = PurePosixPath(f'/api/{settings.OPTIONAL_API_URLPATTERN_PREFIX}/v2/')
+
+        url_path_original = url_path
+        url_path = PurePosixPath(url_path)
+
+        if set(optional_prefix.parts).issubset(set(url_path.parts)):
+            url_prefix = optional_prefix
+        elif set(default_prefix.parts).issubset(set(url_path.parts)):
+            url_prefix = default_prefix
+        else:
+            return url_path_original
+
+        # Remove prefix
+        url_path = PurePosixPath(*url_path.parts[len(url_prefix.parts) :])
+        try:
+            resource_path = PurePosixPath(url_path.parts[0])
+            name = url_path.parts[1]
+            url_suffix = PurePosixPath(*url_path.parts[2:])  # remove name and resource
+        except IndexError:
+            return url_path_original
+
+        resource = resource_path.parts[0]
         if resource in settings.NAMED_URL_MAPPINGS:
-            url_units[4] = cls._named_url_to_pk(settings.NAMED_URL_GRAPH[settings.NAMED_URL_MAPPINGS[resource]], resource, url_units[4])
-        return '/'.join(url_units)
+            pk = PurePosixPath(cls._named_url_to_pk(settings.NAMED_URL_GRAPH[settings.NAMED_URL_MAPPINGS[resource]], resource, name))
+        else:
+            return url_path_original
+
+        parts = url_prefix.parts + resource_path.parts + pk.parts + url_suffix.parts
+        return PurePosixPath(*parts).as_posix() + '/'
 
     def process_request(self, request):
         old_path = request.path_info
diff --git a/awx/main/tests/functional/test_named_url.py b/awx/main/tests/functional/test_named_url.py
index 54e3b96eddb9..d093307c7c70 100644
--- a/awx/main/tests/functional/test_named_url.py
+++ b/awx/main/tests/functional/test_named_url.py
@@ -205,3 +205,65 @@ def test_403_vs_404(get):
 
     get(f'/api/v2/users/{cindy.pk}/', expect=401)
     get('/api/v2/users/cindy/', expect=404)
+
+
+@pytest.mark.django_db
+class TestConvertNamedUrl:
+    @pytest.mark.parametrize(
+        "url",
+        (
+            "/api/",
+            "/api/v2/",
+            "/api/v2/hosts/",
+            "/api/v2/hosts/1/",
+            "/api/v2/organizations/1/inventories/",
+            "/api/foo/",
+            "/api/foo/v2/",
+            "/api/foo/v2/organizations/",
+            "/api/foo/v2/organizations/1/",
+            "/api/foo/v2/organizations/1/inventories/",
+            "/api/foobar/",
+            "/api/foobar/v2/",
+            "/api/foobar/v2/organizations/",
+            "/api/foobar/v2/organizations/1/",
+            "/api/foobar/v2/organizations/1/inventories/",
+            "/api/foobar/v2/organizations/1/inventories/",
+        ),
+    )
+    def test_noop(self, url):
+        settings.OPTIONAL_API_URLPATTERN_PREFIX = ''
+        assert URLModificationMiddleware._convert_named_url(url) == url
+
+        settings.OPTIONAL_API_URLPATTERN_PREFIX = 'foo'
+        assert URLModificationMiddleware._convert_named_url(url) == url
+
+    def test_named_org(self):
+        test_org = Organization.objects.create(name='test_org')
+
+        assert URLModificationMiddleware._convert_named_url('/api/v2/organizations/test_org/') == f'/api/v2/organizations/{test_org.pk}/'
+
+    def test_named_org_optional_api_urlpattern_prefix_interaction(self, settings):
+        settings.OPTIONAL_API_URLPATTERN_PREFIX = 'bar'
+        test_org = Organization.objects.create(name='test_org')
+
+        assert URLModificationMiddleware._convert_named_url('/api/bar/v2/organizations/test_org/') == f'/api/bar/v2/organizations/{test_org.pk}/'
+
+    @pytest.mark.parametrize("prefix", ['', 'bar'])
+    def test_named_org_not_found(self, prefix, settings):
+        settings.OPTIONAL_API_URLPATTERN_PREFIX = prefix
+        if prefix:
+            prefix += '/'
+
+        assert URLModificationMiddleware._convert_named_url(f'/api/{prefix}v2/organizations/does-not-exist/') == f'/api/{prefix}v2/organizations/0/'
+
+    @pytest.mark.parametrize("prefix", ['', 'bar'])
+    def test_named_sub_resource(self, prefix, settings):
+        settings.OPTIONAL_API_URLPATTERN_PREFIX = prefix
+        test_org = Organization.objects.create(name='test_org')
+        if prefix:
+            prefix += '/'
+
+        assert (
+            URLModificationMiddleware._convert_named_url(f'/api/{prefix}v2/organizations/test_org/inventories/')
+            == f'/api/{prefix}v2/organizations/{test_org.pk}/inventories/'
+        )