diff --git a/enterprise_catalog/apps/catalog/algolia_utils.py b/enterprise_catalog/apps/catalog/algolia_utils.py
index 80e9cc23..fe55566d 100644
--- a/enterprise_catalog/apps/catalog/algolia_utils.py
+++ b/enterprise_catalog/apps/catalog/algolia_utils.py
@@ -30,6 +30,8 @@
     RESTRICTION_FOR_B2B,
     VIDEO,
 )
+from enterprise_catalog.apps.catalog.content_metadata_utils import \
+    get_advertised_course_run as imported_get_advertised_course_run
 from enterprise_catalog.apps.catalog.content_metadata_utils import (
     get_course_first_paid_enrollable_seat_price,
     get_course_run_by_uuid,
@@ -1179,10 +1181,9 @@ def get_advertised_course_run(course):
         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 _get_course_run(course, full_course_run)
+    if advertised_course_run := imported_get_advertised_course_run(course):
+        return _get_course_run(course, advertised_course_run)
+    return advertised_course_run
 
 
 def get_course_runs(course):
diff --git a/enterprise_catalog/apps/catalog/content_metadata_utils.py b/enterprise_catalog/apps/catalog/content_metadata_utils.py
index da894034..088d0fdd 100644
--- a/enterprise_catalog/apps/catalog/content_metadata_utils.py
+++ b/enterprise_catalog/apps/catalog/content_metadata_utils.py
@@ -102,3 +102,20 @@ def get_course_first_paid_enrollable_seat_price(course):
         if 'first_enrollable_paid_seat_price' in course_run:
             return course_run['first_enrollable_paid_seat_price']
     return None
+
+
+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
diff --git a/enterprise_catalog/apps/catalog/models.py b/enterprise_catalog/apps/catalog/models.py
index aaaf7999..b397150c 100644
--- a/enterprise_catalog/apps/catalog/models.py
+++ b/enterprise_catalog/apps/catalog/models.py
@@ -45,6 +45,7 @@
     json_serialized_course_modes,
 )
 from enterprise_catalog.apps.catalog.content_metadata_utils import (
+    get_advertised_course_run,
     get_course_first_paid_enrollable_seat_price,
 )
 from enterprise_catalog.apps.catalog.utils import (
@@ -555,10 +556,15 @@ 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_run_key = content_key
+            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,
             )
 
         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/tests/test_serializers.py b/enterprise_catalog/apps/catalog/tests/test_serializers.py
index 78ada547..82430e96 100644
--- a/enterprise_catalog/apps/catalog/tests/test_serializers.py
+++ b/enterprise_catalog/apps/catalog/tests/test_serializers.py
@@ -8,11 +8,13 @@
     COURSE,
     EXEC_ED_2U_COURSE_TYPE,
 )
+from enterprise_catalog.apps.catalog.content_metadata_utils import (
+    get_course_run_by_uuid,
+)
 from enterprise_catalog.apps.catalog.serializers import (
     NormalizedContentMetadataSerializer,
 )
 from enterprise_catalog.apps.catalog.tests import factories
-from enterprise_catalog.apps.catalog.utils import get_course_run_by_uuid
 
 
 @ddt.ddt
diff --git a/enterprise_catalog/apps/catalog/utils.py b/enterprise_catalog/apps/catalog/utils.py
index 7a046424..ada81ea9 100644
--- a/enterprise_catalog/apps/catalog/utils.py
+++ b/enterprise_catalog/apps/catalog/utils.py
@@ -158,21 +158,3 @@ def to_timestamp(datetime_str):
     except (ValueError, TypeError) as exc:
         LOGGER.error(f"[to_timestamp][{exc}] Could not parse date string: {datetime_str}")
         return None
-
-
-def get_course_run_by_uuid(course, course_run_uuid):
-    """
-    Find a course_run based on uuid
-
-    Arguments:
-        course (dict): course dict
-        course_run_uuid (str): uuid to lookup
-
-    Returns:
-        dict: a course_run or None
-    """
-    try:
-        course_run = [run for run in course.get('course_runs', []) if run.get('uuid') == course_run_uuid][0]
-    except IndexError:
-        return None
-    return course_run