diff --git a/openedx/features/course_duration_limits/access.py b/openedx/features/course_duration_limits/access.py
index 7b4ab5d370..ddcc5e5525 100644
--- a/openedx/features/course_duration_limits/access.py
+++ b/openedx/features/course_duration_limits/access.py
@@ -139,8 +139,9 @@ def register_course_expired_message(request, course):
         if upgrade_deadline is None:
             return
         now = timezone.now()
-        if now < upgrade_deadline:
-            upgrade_deadline = enrollment.course_upgrade_deadline
+        course_upgrade_deadline = enrollment.course_upgrade_deadline
+        if now > upgrade_deadline:
+            upgrade_deadline = course_upgrade_deadline
 
         expiration_message = _('{strong_open}Audit Access Expires {expiration_date}{strong_close}'
                                '{line_break}You lose all access to this course, including your progress, on '
@@ -149,7 +150,7 @@ def register_course_expired_message(request, course):
                                      'as long as it exists on the site. {a_open}Upgrade now{sronly_span_open} to '
                                      'retain access past {expiration_date}{span_close}{a_close}')
         full_message = expiration_message
-        if now < upgrade_deadline:
+        if now < course_upgrade_deadline:
             full_message += upgrade_deadline_message
 
         PageLevelMessages.register_info_message(