diff --git a/allianceauth/services/modules/discord/manager.py b/allianceauth/services/modules/discord/manager.py
index 53406bdd..08e1d1f5 100644
--- a/allianceauth/services/modules/discord/manager.py
+++ b/allianceauth/services/modules/discord/manager.py
@@ -32,7 +32,7 @@ SCOPES = [
     'guilds.join',
 ]
 
-GROUP_CACHE_MAX_AGE = int(getattr(settings, 'DISCORD_GROUP_CACHE_MAX_AGE', 2 * 60 * 60))  # 2 hours default
+GROUP_CACHE_MAX_AGE = getattr(settings, 'DISCORD_GROUP_CACHE_MAX_AGE', 2 * 60 * 60)  # 2 hours default
 
 
 class DiscordApiException(Exception):
@@ -301,13 +301,38 @@ class DiscordOAuthManager:
     def _create_group(name):
         return DiscordOAuthManager.__generate_role(name)
 
+    @staticmethod
+    def _get_user(user_id):
+        custom_headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
+        path = DISCORD_URL + "/guilds/" + str(settings.DISCORD_GUILD_ID) + "/members/" + str(user_id)
+        r = requests.get(path, headers=custom_headers)
+        r.raise_for_status()
+        return r.json()
+
+    @staticmethod
+    def _get_user_roles(user_id):
+        user = DiscordOAuthManager._get_user(user_id)
+        return user['roles']
+
+    @staticmethod
+    def _modify_user_role(user_id, role_id, method):
+        custom_headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
+        path = DISCORD_URL + "/guilds/" + str(settings.DISCORD_GUILD_ID) + "/members/" + str(user_id) + "/roles/" + str(
+            role_id)
+        r = getattr(requests, method)(path, headers=custom_headers)
+        r.raise_for_status()
+        logger.debug("%s role %s for user %s" % (method, role_id, user_id))
+
     @staticmethod
     @api_backoff
     def update_groups(user_id, groups):
-        custom_headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
         group_ids = [DiscordOAuthManager._group_name_to_id(DiscordOAuthManager._sanitize_group_name(g)) for g in groups]
-        path = DISCORD_URL + "/guilds/" + str(settings.DISCORD_GUILD_ID) + "/members/" + str(user_id)
-        data = {'roles': group_ids}
-        r = requests.patch(path, headers=custom_headers, json=data)
-        logger.debug("Received status code %s after setting user roles" % r.status_code)
-        r.raise_for_status()
+        user_group_ids = DiscordOAuthManager._get_user_roles(user_id)
+        for g in group_ids:
+            if g not in user_group_ids:
+                DiscordOAuthManager._modify_user_role(user_id, g, 'put')
+                time.sleep(1)  # we're gonna be hammering the API here
+        for g in user_group_ids:
+            if g not in group_ids:
+                DiscordOAuthManager._modify_user_role(user_id, g, 'delete')
+                time.sleep(1)
diff --git a/allianceauth/services/modules/discord/tests.py b/allianceauth/services/modules/discord/tests.py
index bb352204..87916fd0 100644
--- a/allianceauth/services/modules/discord/tests.py
+++ b/allianceauth/services/modules/discord/tests.py
@@ -327,54 +327,54 @@ class DiscordManagerTestCase(TestCase):
         # Assert
         self.assertTrue(result)
 
+    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_user_roles')
     @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_groups')
     @requests_mock.Mocker()
-    def test_update_groups(self, group_cache, m):
+    def test_update_groups(self, group_cache, user_roles, m):
         # Arrange
         groups = ['Member', 'Blue', 'SpecialGroup']
 
-        group_cache.return_value = [{'id': 111, 'name': 'Member'},
-                                    {'id': 222, 'name': 'Blue'},
-                                    {'id': 333, 'name': 'SpecialGroup'},
-                                    {'id': 444, 'name': 'NotYourGroup'}]
+        group_cache.return_value = [{'id': '111', 'name': 'Member'},
+                                    {'id': '222', 'name': 'Blue'},
+                                    {'id': '333', 'name': 'SpecialGroup'},
+                                    {'id': '444', 'name': 'NotYourGroup'}]
+        user_roles.return_value = ['444']
 
         headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
         user_id = 12345
-        request_url = '{}/guilds/{}/members/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id)
+        user_request_url = '{}/guilds/{}/members/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id)
+        group_request_urls = ['{}/guilds/{}/members/{}/roles/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id, g['id']) for g in group_cache.return_value]
 
-        m.patch(request_url,
-                request_headers=headers)
+        m.patch(user_request_url, request_headers=headers)
+        [m.put(url, request_headers=headers) for url in group_request_urls[:-1]]
+        m.delete(group_request_urls[-1], request_headers=headers)
 
         # Act
         DiscordOAuthManager.update_groups(user_id, groups)
 
         # Assert
-        self.assertEqual(len(m.request_history), 1, 'Must be one HTTP call made')
-        history = json.loads(m.request_history[0].text)
-        self.assertIn('roles', history, "'The request must send JSON object with the 'roles' key")
-        self.assertIn(111, history['roles'], 'The group id 111 must be added to the request')
-        self.assertIn(222, history['roles'], 'The group id 222 must be added to the request')
-        self.assertIn(333, history['roles'], 'The group id 333 must be added to the request')
-        self.assertNotIn(444, history['roles'], 'The group id 444 must NOT be added to the request')
+        self.assertEqual(len(m.request_history), 4, 'Must be 4 HTTP calls made')
 
     @mock.patch(MODULE_PATH + '.manager.cache')
-    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_groups')
+    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_user_roles')
+    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._group_name_to_id')
     @requests_mock.Mocker()
-    def test_update_groups_backoff(self, group_cache, djcache, m):
+    def test_update_groups_backoff(self, name_to_id, user_groups, djcache, m):
         # Arrange
         groups = ['Member']
-        group_cache.return_value = [{'id': 111, 'name': 'Member'}]
+        user_groups.return_value = []
+        name_to_id.return_value = '111'
 
         headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
         user_id = 12345
-        request_url = '{}/guilds/{}/members/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id)
+        request_url = '{}/guilds/{}/members/{}/roles/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id, name_to_id.return_value)
 
         djcache.get.return_value = None  # No existing backoffs in cache
 
-        m.patch(request_url,
-                request_headers=headers,
-                headers={'Retry-After': '200000'},
-                status_code=429)
+        m.put(request_url,
+              request_headers=headers,
+              headers={'Retry-After': '200000'},
+              status_code=429)
 
         # Act & Assert
         with self.assertRaises(manager.DiscordApiBackoff) as bo:
@@ -391,23 +391,25 @@ class DiscordManagerTestCase(TestCase):
         self.assertTrue(datetime.datetime.strptime(args[1], manager.cache_time_format) > datetime.datetime.now())
 
     @mock.patch(MODULE_PATH + '.manager.cache')
-    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_groups')
+    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._get_user_roles')
+    @mock.patch(MODULE_PATH + '.manager.DiscordOAuthManager._group_name_to_id')
     @requests_mock.Mocker()
-    def test_update_groups_global_backoff(self, group_cache, djcache, m):
+    def test_update_groups_global_backoff(self, name_to_id, user_groups, djcache, m):
         # Arrange
         groups = ['Member']
-        group_cache.return_value = [{'id': 111, 'name': 'Member'}]
+        user_groups.return_value = []
+        name_to_id.return_value = '111'
 
         headers = {'content-type': 'application/json', 'authorization': 'Bot ' + settings.DISCORD_BOT_TOKEN}
         user_id = 12345
-        request_url = '{}/guilds/{}/members/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id)
+        request_url = '{}/guilds/{}/members/{}/roles/{}'.format(manager.DISCORD_URL, settings.DISCORD_GUILD_ID, user_id, name_to_id.return_value)
 
         djcache.get.return_value = None  # No existing backoffs in cache
 
-        m.patch(request_url,
-                request_headers=headers,
-                headers={'Retry-After': '200000', 'X-RateLimit-Global': 'true'},
-                status_code=429)
+        m.put(request_url,
+              request_headers=headers,
+              headers={'Retry-After': '200000', 'X-RateLimit-Global': 'true'},
+              status_code=429)
 
         # Act & Assert
         with self.assertRaises(manager.DiscordApiBackoff) as bo: