diff --git a/test/api/v3/integration/chat/POST-groups_id_chat_id_clear_flags.test.js b/test/api/v3/integration/chat/POST-groups_id_chat_id_clear_flags.test.js
index b3d410675a..35a2878847 100644
--- a/test/api/v3/integration/chat/POST-groups_id_chat_id_clear_flags.test.js
+++ b/test/api/v3/integration/chat/POST-groups_id_chat_id_clear_flags.test.js
@@ -3,6 +3,7 @@ import {
   generateUser,
   translate as t,
 } from '../../../../helpers/api-v3-integration.helper';
+import config from '../../../../../config.json';
 import { v4 as generateUUID } from 'uuid';
 
 describe('POST /groups/:id/chat/:id/clearflags', () => {
@@ -74,7 +75,7 @@ describe('POST /groups/:id/chat/:id/clearflags', () => {
       expect(messages[0].flagCount).to.eql(0);
     });
 
-    it('can unflag a system message', async () => {
+    it('can\'t flag a system message', async () => {
       let { group, members } = await createAndPopulateGroup({
         groupDetails: {
           type: 'party',
@@ -95,13 +96,15 @@ describe('POST /groups/:id/chat/:id/clearflags', () => {
       await member.post('/user/class/cast/mpheal');
 
       let [skillMsg] = await member.get(`/groups/${group.id}/chat`);
-
-      await member.post(`/groups/${group._id}/chat/${skillMsg.id}/flag`);
-      await admin.post(`/groups/${group._id}/chat/${skillMsg.id}/clearflags`);
-
-      let messages = await members[0].get(`/groups/${group._id}/chat`);
-      expect(messages[0].id).to.eql(skillMsg.id);
-      expect(messages[0].flagCount).to.eql(0);
+      await expect(member.post(`/groups/${group._id}/chat/${skillMsg.id}/flag`))
+        .to.eventually.be.rejected.and.eql({
+          code: 400,
+          error: 'BadRequest',
+          message: t('messageCannotFlagSystemMessages', {communityManagerEmail: config.EMAILS.COMMUNITY_MANAGER_EMAIL}),
+        });
+      // let messages = await members[0].get(`/groups/${group._id}/chat`);
+      // expect(messages[0].id).to.eql(skillMsg.id);
+      // expect(messages[0].flagCount).to.eql(0);
     });
   });
 
diff --git a/website/client/components/chat/chatMessages.vue b/website/client/components/chat/chatMessages.vue
index 176106f32a..ad5524cbad 100644
--- a/website/client/components/chat/chatMessages.vue
+++ b/website/client/components/chat/chatMessages.vue
@@ -41,7 +41,7 @@
                 .svg-icon(v-html="icons.copy")
                 | {{$t('copyAsTodo')}}
                 // @TODO make copyAsTodo work in the inbox
-            span.action(v-if='!inbox && user.flags.communityGuidelinesAccepted', @click='report(msg)')
+            span.action(v-if='!inbox && user.flags.communityGuidelinesAccepted && msg.uuid !== "system"', @click='report(msg)')
               .svg-icon(v-html="icons.report")
               | {{$t('report')}}
               // @TODO make flagging/reporting work in the inbox. NOTE: it must work even if the communityGuidelines are not accepted and it MUST work for messages that you have SENT as well as received. -- Alys
diff --git a/website/common/locales/en/messages.json b/website/common/locales/en/messages.json
index 2bef686376..64eb2cd9a4 100644
--- a/website/common/locales/en/messages.json
+++ b/website/common/locales/en/messages.json
@@ -1,5 +1,4 @@
 {
-
   "messageLostItem": "Your <%= itemText %> broke.",
   "messageTaskNotFound": "Task not found.",
   "messageDuplicateTaskID": "A task with that ID already exists.",
@@ -58,6 +57,7 @@
   "messageGroupChatFlagAlreadyReported": "You have already reported this message",
   "messageGroupChatNotFound": "Message not found!",
   "messageGroupChatAdminClearFlagCount": "Only an admin can clear the flag count!",
+  "messageCannotFlagSystemMessages": "You cannot flag a system message. If you need to report a violation of the Community Guidelines related to this message, please email a screenshot and explanation to Lemoness at <%= communityManagerEmail %>.",
   "messageGroupChatSpam": "Whoops, looks like you're posting too many messages! Please wait a minute and try again. The Tavern chat only holds 200 messages at a time, so Habitica encourages posting longer, more thoughtful messages and consolidating replies. Can't wait to hear what you have to say. :)",
 
   "messageUserOperationProtected": "path `<%= operation %>` was not saved, as it's a protected path.",
diff --git a/website/server/controllers/api-v3/chat.js b/website/server/controllers/api-v3/chat.js
index e5de5e5608..88687c43c1 100644
--- a/website/server/controllers/api-v3/chat.js
+++ b/website/server/controllers/api-v3/chat.js
@@ -22,6 +22,7 @@ const FLAG_REPORT_EMAILS = nconf.get('FLAG_REPORT_EMAIL').split(',').map((email)
   return { email, canSend: true };
 });
 
+const COMMUNITY_MANAGER_EMAIL = nconf.get('EMAILS:COMMUNITY_MANAGER_EMAIL');
 /**
  * @apiDefine MessageNotFound
  * @apiError (404) {NotFound} MessageNotFound The specified message could not be found.
@@ -320,7 +321,7 @@ api.flagChat = {
     let message = _.find(group.chat, {id: req.params.chatId});
 
     if (!message) throw new NotFound(res.t('messageGroupChatNotFound'));
-
+    if (message.uuid === 'system') throw new BadRequest(res.t('messageCannotFlagSystemMessages', {communityManagerEmail: COMMUNITY_MANAGER_EMAIL}));
     let update = {$set: {}};
 
     // Log user ids that have flagged the message