diff --git a/common/djangoapps/entitlements/models.py b/common/djangoapps/entitlements/models.py
index 735933bf79..9bce945d15 100644
--- a/common/djangoapps/entitlements/models.py
+++ b/common/djangoapps/entitlements/models.py
@@ -260,13 +260,29 @@ class CourseEntitlement(TimeStampedModel):
     @classmethod
     def get_entitlement_if_active(cls, user, course_uuid):
         """
-        Returns an entitlement for a given course uuid if an active entitlement exists, otherwise returns None.
+        Retrieves the active entitlement for the course_uuid and User.
+
         An active entitlement is defined as an entitlement that has not yet expired or has a currently enrolled session.
+        If there is more than one entitlement, return the most recently created active entitlement.
+
+        Arguments:
+            user: User that owns the Course Entitlement
+            course_uuid: The Course UUID for a Course that we are retrieving active entitlements for.
+
+        Returns:
+            CourseEntitlement: Returns the most recently created entitlement for a given course uuid if an
+                               active entitlement exists, otherwise returns None
         """
-        return cls.objects.filter(
-            user=user,
-            course_uuid=course_uuid
-        ).exclude(expired_at__isnull=False, enrollment_course_run=None).first()
+        try:
+            return cls.objects.filter(
+                user=user,
+                course_uuid=course_uuid
+            ).exclude(
+                expired_at__isnull=False,
+                enrollment_course_run=None
+            ).latest('created')
+        except CourseEntitlement.DoesNotExist:
+            return None
 
     @classmethod
     def get_active_entitlements_for_user(cls, user):
diff --git a/common/djangoapps/student/views.py b/common/djangoapps/student/views.py
index 1adde03085..309cb495eb 100644
--- a/common/djangoapps/student/views.py
+++ b/common/djangoapps/student/views.py
@@ -800,12 +800,11 @@ def dashboard(request):
     urls, program_data = {}, {}
     bundles_on_dashboard_flag = WaffleFlag(WaffleFlagNamespace(name=u'student.experiments'), u'bundles_on_dashboard')
 
-    if (bundles_on_dashboard_flag.is_enabled()):
+    if bundles_on_dashboard_flag.is_enabled():
         programs_data = meter.programs
         if programs_data:
             program_data = meter.programs[0]
             program_data = ProgramDataExtender(program_data, request.user).extend()
-            course_data = meter.progress(programs=[program_data], count_only=False)[0]
 
             program_data.pop('courses')
             skus = program_data.get('skus')
diff --git a/openedx/core/djangoapps/programs/tests/test_utils.py b/openedx/core/djangoapps/programs/tests/test_utils.py
index 0d481284c6..b123f02a45 100644
--- a/openedx/core/djangoapps/programs/tests/test_utils.py
+++ b/openedx/core/djangoapps/programs/tests/test_utils.py
@@ -179,6 +179,54 @@ class TestProgramProgressMeter(TestCase):
         program = data[0]
         self.assertEqual(meter.engaged_programs, [program])
 
+    def test_single_program_multiple_entitlements(self, mock_get_programs):
+        """
+        Verify that the most recent entitlement is returned when a user has multiple for the same course
+        """
+        course_uuid = uuid.uuid4()
+        data = [
+            ProgramFactory(courses=[CourseFactory(uuid=str(course_uuid))]),
+            ProgramFactory(),
+        ]
+        mock_get_programs.return_value = data
+        course_run_key = generate_course_run_key()
+        course_run_key2 = generate_course_run_key()
+
+        enrollment = CourseEnrollmentFactory(
+            user=self.user,
+            course_id=course_run_key,
+            mode=CourseMode.VERIFIED,
+            is_active=False
+        )
+        enrollment2 = CourseEnrollmentFactory(
+            user=self.user,
+            course_id=course_run_key2,
+            mode=CourseMode.VERIFIED
+        )
+
+        CourseEntitlementFactory.create(
+            user=self.user,
+            course_uuid=course_uuid,
+            expired_at=datetime.datetime.now(utc),
+            mode=CourseMode.VERIFIED,
+            enrollment_course_run=enrollment
+
+        )
+        CourseEntitlementFactory.create(
+            user=self.user,
+            course_uuid=course_uuid,
+            mode=CourseMode.VERIFIED,
+            enrollment_course_run=enrollment2
+        )
+
+        meter = ProgramProgressMeter(self.site, self.user)
+        self._attach_detail_url(data)
+        self.assertEqual(len(meter.entitlements), 1)
+
+        entitlement = meter.entitlements[0]
+        self.assertIsNone(entitlement.expired_at)
+        self.assertEqual(entitlement.enrollment_course_run.course_id, enrollment2.course_id)
+
     def test_course_progress(self, mock_get_programs):
         """
         Verify that the progress meter can represent progress in terms of
diff --git a/openedx/core/djangoapps/programs/utils.py b/openedx/core/djangoapps/programs/utils.py
index 8447dbd8d8..ccae2ddaa2 100644
--- a/openedx/core/djangoapps/programs/utils.py
+++ b/openedx/core/djangoapps/programs/utils.py
@@ -237,7 +237,10 @@ class ProgramProgressMeter(object):
                 elif self._is_course_enrolled(course) or active_entitlement:
                     # Show all currently enrolled courses and active entitlements as in progress
                     if active_entitlement:
-                        course['course_runs'] = get_fulfillable_course_runs_for_entitlement(active_entitlement, course['course_runs'])
+                        course['course_runs'] = get_fulfillable_course_runs_for_entitlement(
+                            active_entitlement,
+                            course['course_runs']
+                        )
                         course['user_entitlement'] = active_entitlement.to_dict()
                         course['enroll_url'] = reverse(
                             'entitlements_api:v1:enrollments',