diff --git a/app/dao/notifications_dao.py b/app/dao/notifications_dao.py
index 645bf9090..c91070eea 100644
--- a/app/dao/notifications_dao.py
+++ b/app/dao/notifications_dao.py
@@ -307,19 +307,14 @@ def delete_notifications_older_than_retention_by_type(notification_type, qry_lim
     ).all()
     deleted = 0
     for f in flexible_data_retention:
-        days_of_retention = get_london_midnight_in_utc(
-            convert_utc_to_bst(datetime.utcnow()).date()) - timedelta(days=f.days_of_retention)
-
-        if notification_type == LETTER_TYPE:
-            _delete_letters_from_s3(
-                notification_type, f.service_id, days_of_retention, qry_limit
-            )
-
-        insert_update_notification_history(notification_type, days_of_retention, f.service_id)
-
         current_app.logger.info(
             "Deleting {} notifications for service id: {}".format(notification_type, f.service_id))
-        deleted += _delete_notifications(notification_type, days_of_retention, f.service_id, qry_limit)
+
+        day_to_delete_backwards_from = get_london_midnight_in_utc(
+            convert_utc_to_bst(datetime.utcnow()).date()) - timedelta(days=f.days_of_retention)
+
+        deleted += _move_notifications_to_notification_history(
+            notification_type, f.service_id, day_to_delete_backwards_from, qry_limit)
 
     current_app.logger.info(
         'Deleting {} notifications for services without flexible data retention'.format(notification_type))
@@ -329,18 +324,54 @@ def delete_notifications_older_than_retention_by_type(notification_type, qry_lim
     service_ids_to_purge = db.session.query(Service.id).filter(Service.id.notin_(services_with_data_retention)).all()
 
     for service_id in service_ids_to_purge:
-        if notification_type == LETTER_TYPE:
-            _delete_letters_from_s3(
-                notification_type, service_id, seven_days_ago, qry_limit
-            )
-        insert_update_notification_history(notification_type, seven_days_ago, service_id)
-        deleted += _delete_notifications(notification_type, seven_days_ago, service_id, qry_limit)
+        deleted += _move_notifications_to_notification_history(
+            notification_type, service_id, seven_days_ago, qry_limit)
 
     current_app.logger.info('Finished deleting {} notifications'.format(notification_type))
 
     return deleted
 
 
+def _move_notifications_to_notification_history(notification_type, service_id, day_to_delete_backwards_from, qry_limit):
+    deleted = 0
+    if notification_type == LETTER_TYPE:
+        _delete_letters_from_s3(
+            notification_type, service_id, day_to_delete_backwards_from, qry_limit
+        )
+
+    stop = -1  # exclusive, we want to include 0
+    step = -1
+    for hour_delta in range(23, stop, step):
+        # We find the timestamp we want to delete all notifications backwards from
+        # We then start 23 hours ago, and do an insert notification history before deleting all notifications older
+        # We then look 22 hours ago, do an insert notifications history before deleting all notifications older
+        # We continue this until we reach the original timestamp we wanted to delete notifications backwardsfrom
+        # This enables us to break this into smaller database queries
+        timestamp_to_delete_backwards_from = day_to_delete_backwards_from - timedelta(hours=hour_delta)
+
+        if service_id == '539d63a1-701d-400d-ab11-f3ee2319d4d4':
+            current_app.logger.info(
+                "Beginning insert_update_notification_history for GOV.UK Email from {} backwards".format(
+                    timestamp_to_delete_backwards_from
+                )
+            )
+
+        insert_update_notification_history(notification_type, timestamp_to_delete_backwards_from, service_id, qry_limit)
+
+        if service_id == '539d63a1-701d-400d-ab11-f3ee2319d4d4':
+            current_app.logger.info(
+                "Beginning _delete_notifications for GOV.UK Email {} backwards".format(
+                    timestamp_to_delete_backwards_from
+                )
+            )
+
+        deleted += _delete_notifications(
+            notification_type, timestamp_to_delete_backwards_from, service_id, qry_limit
+        )
+
+    return deleted
+
+
 def _delete_notifications(notification_type, date_to_delete_from, service_id, query_limit):
     subquery = db.session.query(
         Notification.id
@@ -389,6 +420,8 @@ def insert_update_notification_history(notification_type, date_to_delete_from, s
         Notification.service_id == service_id,
         Notification.created_at < date_to_delete_from,
         Notification.key_type != KEY_TYPE_TEST
+    ).order_by(
+        Notification.created_at
     )
     notifications_count = notification_query.count()