diff --git a/openedx/features/discounts/applicability.py b/openedx/features/discounts/applicability.py
index 3fa32ae920..0c2bb26ea1 100644
--- a/openedx/features/discounts/applicability.py
+++ b/openedx/features/discounts/applicability.py
@@ -9,6 +9,7 @@ not other discounts like coupons or enterprise/program offers configured in ecom
 
 """
 from course_modes.models import CourseMode
+from entitlements.models import CourseEntitlement
 from openedx.core.djangoapps.waffle_utils import WaffleFlag, WaffleFlagNamespace
 from openedx.features.discounts.models import DiscountRestrictionConfig
 from student.models import CourseEnrollment
@@ -61,6 +62,10 @@ def can_receive_discount(user, course):  # pylint: disable=unused-argument
     if CourseEnrollment.objects.filter(user=user).exclude(mode__in=CourseMode.UPSELL_TO_VERIFIED_MODES).exists():
         return False
 
+    # Don't allow any users who have entitlements (past or present)
+    if CourseEntitlement.objects.filter(user=user).exists():
+        return False
+
     return True
 
 
diff --git a/openedx/features/discounts/tests/test_applicability.py b/openedx/features/discounts/tests/test_applicability.py
index 160587003b..bd5c7d7e01 100644
--- a/openedx/features/discounts/tests/test_applicability.py
+++ b/openedx/features/discounts/tests/test_applicability.py
@@ -7,6 +7,7 @@ from django.utils.timezone import now
 
 from course_modes.models import CourseMode
 from course_modes.tests.factories import CourseModeFactory
+from entitlements.tests.factories import CourseEntitlementFactory
 from openedx.core.djangoapps.content.course_overviews.models import CourseOverview
 from openedx.core.djangoapps.waffle_utils.testutils import override_waffle_flag
 from openedx.features.discounts.models import DiscountRestrictionConfig
@@ -78,3 +79,19 @@ class TestApplicability(ModuleStoreTestCase):
 
         applicability = can_receive_discount(user=self.user, course=self.course)
         assert applicability == all(mode in CourseMode.UPSELL_TO_VERIFIED_MODES for mode in existing_enrollments)
+
+    @ddt.data(
+        None,
+        CourseMode.VERIFIED,
+        CourseMode.PROFESSIONAL,
+    )
+    @override_waffle_flag(DISCOUNT_APPLICABILITY_FLAG, active=True)
+    def test_can_receive_discount_entitlement(self, entitlement_mode):
+        """
+        Ensure that only users who have not already purchased courses receive the discount.
+        """
+        if entitlement_mode is not None:
+            CourseEntitlementFactory.create(mode=entitlement_mode, user=self.user)
+
+        applicability = can_receive_discount(user=self.user, course=self.course)
+        assert applicability == (entitlement_mode is None)
diff --git a/openedx/tests/settings.py b/openedx/tests/settings.py
index 4dd346c915..b31f7846e0 100644
--- a/openedx/tests/settings.py
+++ b/openedx/tests/settings.py
@@ -94,6 +94,7 @@ INSTALLED_APPS = (
 
     # Django 1.11 demands to have imported models supported by installed apps.
     'completion',
+    'entitlements',
 )
 
 LMS_ROOT_URL = "http://localhost:8000"