diff --git a/enterprise_catalog/apps/catalog/models.py b/enterprise_catalog/apps/catalog/models.py
index aaaf7999..3774b567 100644
--- a/enterprise_catalog/apps/catalog/models.py
+++ b/enterprise_catalog/apps/catalog/models.py
@@ -50,6 +50,7 @@
 from enterprise_catalog.apps.catalog.utils import (
     batch,
     enterprise_proxy_login_url,
+    get_advertised_course_run,
     get_content_filter_hash,
     get_content_key,
     get_content_type,
@@ -555,10 +556,16 @@ def get_content_enrollment_url(self, content_metadata):
         else:
             # Catalog param only needed for legacy (non-learner-portal) enrollment URLs
             params['catalog'] = self.uuid
+
+            course_key = content_key if parent_content_key else None
+            course_run_key = content_key if not parent_content_key else None
+            if not parent_content_key:
+                if advertised_course_run := get_advertised_course_run(content_metadata.json_metadata):
+                    course_run_key = advertised_course_run['key']
             url = '{}/enterprise/{}/course/{}/enroll/'.format(
                 settings.LMS_BASE_URL,
                 self.enterprise_uuid,
-                content_key,
+                course_run_key or course_key,
             )
 
         return update_query_parameters(url, params)
diff --git a/enterprise_catalog/apps/catalog/tests/factories.py b/enterprise_catalog/apps/catalog/tests/factories.py
index 45fab4b4..93ef6394 100644
--- a/enterprise_catalog/apps/catalog/tests/factories.py
+++ b/enterprise_catalog/apps/catalog/tests/factories.py
@@ -99,7 +99,7 @@ def _json_metadata(self):
                 'logo_image_url': fake.image_url() + '.jpg',
             }]
             course_runs = [{
-                'key': 'course-v1:edX+DemoX',
+                'key': 'course-v1:edX+DemoX+2T2024',
                 'uuid': str(FAKE_ADVERTISED_COURSE_RUN_UUID),
                 'content_language': 'en-us',
                 'status': 'published',
diff --git a/enterprise_catalog/apps/catalog/tests/test_models.py b/enterprise_catalog/apps/catalog/tests/test_models.py
index 03b7367f..47f97e32 100644
--- a/enterprise_catalog/apps/catalog/tests/test_models.py
+++ b/enterprise_catalog/apps/catalog/tests/test_models.py
@@ -623,6 +623,46 @@ def test_get_content_enrollment_url(
         else:
             assert settings.LMS_BASE_URL in content_enrollment_url
 
+    @ddt.data(
+        {
+            'content_key': 'course-v1:edX+DemoX+2T2024',
+            'parent_content_key': 'edX+DemoX',
+        },
+        {
+            'content_key': 'edX+DemoX',
+            'parent_content_key': None
+        },
+    )
+    @ddt.unpack
+    def test_get_content_enrollment_url_disabled_learner_portal(
+        self,
+        content_key,
+        parent_content_key,
+    ):
+        enterprise_uuid = uuid4()
+        enterprise_slug = 'sluggy'
+
+        enterprise_catalog = factories.EnterpriseCatalogFactory(enterprise_uuid=enterprise_uuid)
+        content_metadata = factories.ContentMetadataFactory(
+            content_key=content_key,
+            parent_content_key=parent_content_key,
+            content_type=COURSE,
+        )
+
+        enterprise_catalog.catalog_query.contentmetadata_set.add(*[content_metadata])
+
+        mock_enterprise_customer_return_value = {
+            'slug': enterprise_slug,
+            'enable_learner_portal': False,
+        }
+
+        with self._mock_enterprise_customer_cache(
+            mock_enterprise_customer_return_value,
+        ):
+            content_enrollment_url = enterprise_catalog.get_content_enrollment_url(content_metadata)
+
+        assert "/course/course-v1:edX+DemoX+2T2024/enroll/" in content_enrollment_url
+
     @mock.patch('enterprise_catalog.apps.api_client.enterprise_cache.EnterpriseApiClient')
     @ddt.data(
         {
diff --git a/enterprise_catalog/apps/catalog/utils.py b/enterprise_catalog/apps/catalog/utils.py
index 7a046424..444bce1e 100644
--- a/enterprise_catalog/apps/catalog/utils.py
+++ b/enterprise_catalog/apps/catalog/utils.py
@@ -176,3 +176,20 @@ def get_course_run_by_uuid(course, course_run_uuid):
     except IndexError:
         return None
     return course_run
+
+
+def get_advertised_course_run(course):
+    """
+    Get part of the advertised course_run as per advertised_course_run_uuid
+
+    Argument:
+        course (dict)
+
+    Returns:
+        dict: containing key, pacing_type, start, end, and upgrade deadline
+        for the course_run, or None
+    """
+    full_course_run = get_course_run_by_uuid(course, course.get('advertised_course_run_uuid'))
+    if full_course_run is None:
+        return None
+    return full_course_run