diff --git a/lms/djangoapps/grades/models.py b/lms/djangoapps/grades/models.py
index 6fed1d8abf..c6cb91b1d8 100644
--- a/lms/djangoapps/grades/models.py
+++ b/lms/djangoapps/grades/models.py
@@ -679,6 +679,7 @@ class PersistentSubsectionGradeOverride(models.Model):
     # model in the grades app, which will fail.
     if 'grades' in apps.app_configs:
         history = HistoricalRecords()
+        _history_user = None
 
     def __str__(self):
         return u', '.join([
@@ -734,15 +735,18 @@ class PersistentSubsectionGradeOverride(models.Model):
             log.info(u'Creating override for user ***{}*** for PersistentSubsectionGrade'
                      u'***{}*** with override data ***{}*** and derived grade_defaults ***{}***.'
                      .format(requesting_user, subsection_grade_model, override_data, grade_defaults))
-        override, _ = PersistentSubsectionGradeOverride.objects.update_or_create(
-            grade=subsection_grade_model,
-            defaults=grade_defaults,
-        )
-
-        override_history_entry = override.history.first()
-        if not override_history_entry.history_user and requesting_user:
-            override_history_entry.history_user = requesting_user
-            override_history_entry.save()
+        try:
+            override = PersistentSubsectionGradeOverride.objects.get(grade=subsection_grade_model)
+            for key, value in six.iteritems(grade_defaults):
+                setattr(override, key, value)
+        except PersistentSubsectionGradeOverride.DoesNotExist:
+            override = PersistentSubsectionGradeOverride(grade=subsection_grade_model, **grade_defaults)
+        if requesting_user:
+            # setting this on a non-field attribute which simple
+            # history reads from to determine which user to attach to
+            # the history row
+            override._history_user = requesting_user  # pylint: disable=protected-access
+        override.save()
 
         return override
 
diff --git a/lms/djangoapps/grades/rest_api/v1/tests/test_gradebook_views.py b/lms/djangoapps/grades/rest_api/v1/tests/test_gradebook_views.py
index ebbde7dab6..6a5046b52c 100644
--- a/lms/djangoapps/grades/rest_api/v1/tests/test_gradebook_views.py
+++ b/lms/djangoapps/grades/rest_api/v1/tests/test_gradebook_views.py
@@ -1813,6 +1813,27 @@ class SubsectionGradeViewTest(GradebookViewTestBase):
 
         assert expected_data == resp.data
 
+    def test_comment_appears(self):
+        """
+        Test that comments passed (e.g. from proctoring) appear in the history rows
+        """
+        proctoring_failure_fake_comment = "Failed Test Proctoring"
+        self.login_course_staff()
+        override = PersistentSubsectionGradeOverride.update_or_create_override(
+            requesting_user=self.global_staff,
+            subsection_grade_model=self.grade,
+            earned_all_override=0.0,
+            earned_graded_override=0.0,
+            feature=GradeOverrideFeatureEnum.proctoring,
+            comment=proctoring_failure_fake_comment
+        )
+
+        resp = self.client.get(
+            self.get_url(subsection_id=self.usage_key)
+        )
+
+        assert resp.data['history'][0]['override_reason'] == proctoring_failure_fake_comment
+
     @ddt.data(
         'login_staff',
     )
diff --git a/lms/djangoapps/grades/services.py b/lms/djangoapps/grades/services.py
index 3d0798e272..713dc26da8 100644
--- a/lms/djangoapps/grades/services.py
+++ b/lms/djangoapps/grades/services.py
@@ -29,7 +29,7 @@ class GradesService(object):
 
     def override_subsection_grade(
             self, user_id, course_key_or_id, usage_key_or_id, earned_all=None, earned_graded=None,
-            feature=api.constants.GradeOverrideFeatureEnum.proctoring
+            feature=api.constants.GradeOverrideFeatureEnum.proctoring, overrider=None, comment=None
     ):
         """
         Creates a PersistentSubsectionGradeOverride corresponding to the given
@@ -46,7 +46,9 @@ class GradesService(object):
                                              usage_key_or_id,
                                              earned_all=earned_all,
                                              earned_graded=earned_graded,
-                                             feature=feature)
+                                             feature=feature,
+                                             overrider=overrider,
+                                             comment=comment)
 
     def undo_override_subsection_grade(self, user_id, course_key_or_id, usage_key_or_id,
                                        feature=api.constants.GradeOverrideFeatureEnum.proctoring):
diff --git a/requirements/edx/base.txt b/requirements/edx/base.txt
index 6d48f10453..7400dc4716 100644
--- a/requirements/edx/base.txt
+++ b/requirements/edx/base.txt
@@ -113,7 +113,7 @@ edx-oauth2-provider==1.3.1
 edx-opaque-keys[django]==2.0.0
 edx-organizations==2.1.0
 edx-proctoring-proctortrack==1.0.5
-edx-proctoring==2.0.9
+edx-proctoring==2.1.0
 edx-rbac==1.0.3           # via edx-enterprise
 edx-rest-api-client==1.9.2
 edx-search==1.2.2
diff --git a/requirements/edx/development.txt b/requirements/edx/development.txt
index 91dbb61564..78a595b1e1 100644
--- a/requirements/edx/development.txt
+++ b/requirements/edx/development.txt
@@ -137,7 +137,7 @@ edx-oauth2-provider==1.3.1
 edx-opaque-keys[django]==2.0.0
 edx-organizations==2.1.0
 edx-proctoring-proctortrack==1.0.5
-edx-proctoring==2.0.9
+edx-proctoring==2.1.0
 edx-rbac==1.0.3
 edx-rest-api-client==1.9.2
 edx-search==1.2.2
diff --git a/requirements/edx/testing.txt b/requirements/edx/testing.txt
index e4686de764..554bef52ce 100644
--- a/requirements/edx/testing.txt
+++ b/requirements/edx/testing.txt
@@ -133,7 +133,7 @@ edx-oauth2-provider==1.3.1
 edx-opaque-keys[django]==2.0.0
 edx-organizations==2.1.0
 edx-proctoring-proctortrack==1.0.5
-edx-proctoring==2.0.9
+edx-proctoring==2.1.0
 edx-rbac==1.0.3
 edx-rest-api-client==1.9.2
 edx-search==1.2.2