diff --git a/common/djangoapps/entitlements/models.py b/common/djangoapps/entitlements/models.py
index 66ddec0231..cae62123ba 100644
--- a/common/djangoapps/entitlements/models.py
+++ b/common/djangoapps/entitlements/models.py
@@ -54,10 +54,11 @@ class CourseEntitlementPolicy(models.Model):
         # Compute the days left for the regain
         days_since_course_start = (now - course_overview.start).days
         days_since_enrollment = (now - entitlement.enrollment_course_run.created).days
+        days_since_entitlement_created = (now - entitlement.created).days
 
         # We want to return whichever days value is less since it is then the more recent one
         days_until_regain_ends = (self.regain_period.days -  # pylint: disable=no-member
-                                  min(days_since_course_start, days_since_enrollment))
+                                  min(days_since_course_start, days_since_enrollment, days_since_entitlement_created))
 
         # If the base days until expiration is less than the days until the regain period ends, use that instead
         if days_until_expiry < days_until_regain_ends:
diff --git a/common/djangoapps/entitlements/tests/test_models.py b/common/djangoapps/entitlements/tests/test_models.py
index 6548939fbf..98f5b9a3e6 100644
--- a/common/djangoapps/entitlements/tests/test_models.py
+++ b/common/djangoapps/entitlements/tests/test_models.py
@@ -175,6 +175,21 @@ class TestModels(TestCase):
         assert expired_at_datetime
         assert entitlement.expired_at
 
+        # Verify that an entitlement that has just been created, but the user has been enrolled in the course for
+        # greater than 14 days, and the course started more than 14 days ago is not expired
+        entitlement = CourseEntitlementFactory.create(enrollment_course_run=self.enrollment)
+        past_datetime = datetime.utcnow().replace(tzinfo=pytz.UTC) - timedelta(days=20)
+        entitlement.created = datetime.utcnow().replace(tzinfo=pytz.UTC)
+        self.enrollment.created = past_datetime
+        self.course.start = past_datetime
+        entitlement.save()
+        self.enrollment.save()
+        self.course.save()
+        assert entitlement.enrollment_course_run
+        expired_at_datetime = entitlement.expired_at_datetime
+        assert expired_at_datetime is None
+        assert entitlement.expired_at is None
+
         # Verify a date 451 days in the past (1 days after the policy expiration)
         # That is enrolled and started in within the regain period is still expired
         entitlement = CourseEntitlementFactory.create(enrollment_course_run=self.enrollment)