diff --git a/test/api/v3/integration/chat/POST-chat.flag.test.js b/test/api/v3/integration/chat/POST-chat.flag.test.js
new file mode 100644
index 0000000000..5f4954d28a
--- /dev/null
+++ b/test/api/v3/integration/chat/POST-chat.flag.test.js
@@ -0,0 +1,126 @@
+import {
+  generateUser,
+  requester,
+  translate as t,
+} from '../../../../helpers/api-integration.helper';
+import _ from 'lodash';
+
+describe('POST /chat/:chatId/flag', () => {
+  let user;
+  let api;
+  let group;
+  let testMessage = 'Test Message';
+
+  before(() => {
+    let groupName = 'Test Guild';
+    let groupType = 'guild';
+    let groupPrivacy = 'public';
+
+    return generateUser({balance: 1}).then((generatedUser) => {
+      user = generatedUser;
+      api = requester(user);
+    })
+    .then(() => {
+      return api.post('/groups', {
+        name: groupName,
+        type: groupType,
+        privacy: groupPrivacy,
+      });
+    })
+    .then((generatedGroup) => {
+      group = generatedGroup;
+    });
+  });
+
+  it('Returns an error when chat message is not found', () => {
+    return expect(api.post(`/groups/${group._id}/chat/incorrectMessage/flag`))
+      .to.eventually.be.rejected.and.eql({
+        code: 404,
+        error: 'NotFound',
+        message: t('messageGroupChatNotFound'),
+      });
+  });
+
+  it('Returns an error when user tries to flag their own message', () => {
+    return api.post(`/groups/${group._id}/chat`, { message: testMessage})
+    .then((result) => {
+      return expect(api.post(`/groups/${group._id}/chat/${result.message.id}/flag`))
+        .to.eventually.be.rejected.and.eql({
+          code: 404,
+          error: 'NotFound',
+          message: t('messageGroupChatFlagOwnMessage'),
+        });
+    });
+  });
+
+  it('Flags a chat', () => {
+    let api2;
+    let message;
+
+    return generateUser().then((generatedUser) => {
+      api2 = requester(generatedUser);
+      return api2.post(`/groups/${group._id}/chat`, { message: testMessage});
+    })
+    .then((result) => {
+      message = result.message;
+      return api.post(`/groups/${group._id}/chat/${message.id}/flag`);
+    })
+    .then((result) => {
+      expect(result.flags[user._id]).to.equal(true);
+      expect(result.flagCount).to.equal(1);
+      return api.get(`/groups/${group._id}`);
+    })
+    .then((updatedGroup) => {
+      let messageToCheck = _.find(updatedGroup.chat, {id: message.id});
+      expect(messageToCheck.flags[user._id]).to.equal(true);
+    });
+  });
+
+  it('Flags a chat with a higher flag acount when an admin flags the message', () => {
+    let api2;
+    let secondUser;
+    let message;
+
+    return generateUser({'contributor.admin': true}).then((generatedUser) => {
+      secondUser = generatedUser;
+      api2 = requester(generatedUser);
+      return api.post(`/groups/${group._id}/chat`, { message: testMessage});
+    })
+    .then((result) => {
+      message = result.message;
+      return api2.post(`/groups/${group._id}/chat/${message.id}/flag`);
+    })
+    .then((result) => {
+      expect(result.flags[secondUser._id]).to.equal(true);
+      expect(result.flagCount).to.equal(5);
+      return api.get(`/groups/${group._id}`);
+    })
+    .then((updatedGroup) => {
+      let messageToCheck = _.find(updatedGroup.chat, {id: message.id});
+      expect(messageToCheck.flags[secondUser._id]).to.equal(true);
+      expect(messageToCheck.flagCount).to.equal(5);
+    });
+  });
+
+  it('Returns an error when user tries to flag a message that is already flagged', () => {
+    let api2;
+    let message;
+
+    return generateUser().then((generatedUser) => {
+      api2 = requester(generatedUser);
+      return api2.post(`/groups/${group._id}/chat`, { message: testMessage});
+    })
+    .then((result) => {
+      message = result.message;
+      return api.post(`/groups/${group._id}/chat/${message.id}/flag`);
+    })
+    .then(() => {
+      return expect(api.post(`/groups/${group._id}/chat/${message.id}/flag`))
+        .to.eventually.be.rejected.and.eql({
+          code: 404,
+          error: 'NotFound',
+          message: t('messageGroupChatFlagAlreadyReported'),
+        });
+    });
+  });
+});
diff --git a/test/api/v3/integration/chat/POST-chat.like.test.js b/test/api/v3/integration/chat/POST-chat.like.test.js
index 1096aa11e3..66403221bd 100644
--- a/test/api/v3/integration/chat/POST-chat.like.test.js
+++ b/test/api/v3/integration/chat/POST-chat.like.test.js
@@ -3,6 +3,7 @@ import {
   requester,
   translate as t,
 } from '../../../../helpers/api-integration.helper';
+import _ from 'lodash';
 
 describe('POST /chat/:chatId/like', () => {
   let user;
@@ -54,15 +55,49 @@ describe('POST /chat/:chatId/like', () => {
 
   it('Likes a chat', () => {
     let api2;
+    let message;
+
     return generateUser().then((generatedUser) => {
       api2 = requester(generatedUser);
       return api2.post(`/groups/${group._id}/chat`, { message: testMessage});
     })
     .then((result) => {
-      return api.post(`/groups/${group._id}/chat/${result.message.id}/like`);
+      message = result.message;
+      return api.post(`/groups/${group._id}/chat/${message.id}/like`);
     })
     .then((result) => {
       expect(result.likes[user._id]).to.equal(true);
+      return api.get(`/groups/${group._id}`);
+    })
+    .then((updatedGroup) => {
+      let messageToCheck = _.find(updatedGroup.chat, {id: message.id});
+      expect(messageToCheck.likes[user._id]).to.equal(true);
+    });
+  });
+
+  it('Unlikes a chat', () => {
+    let api2;
+    let message;
+
+    return generateUser().then((generatedUser) => {
+      api2 = requester(generatedUser);
+      return api2.post(`/groups/${group._id}/chat`, { message: testMessage});
+    })
+    .then((result) => {
+      message = result.message;
+      return api.post(`/groups/${group._id}/chat/${message.id}/like`);
+    })
+    .then((result) => {
+      expect(result.likes[user._id]).to.equal(true);
+      return api.post(`/groups/${group._id}/chat/${message.id}/like`);
+    })
+    .then((result) => {
+      expect(result.likes[user._id]).to.equal(undefined);
+      return api.get(`/groups/${group._id}`);
+    })
+    .then((updatedGroup) => {
+      let messageToCheck = _.find(updatedGroup.chat, {id: message.id});
+      expect(messageToCheck.likes[user._id]).to.equal(undefined);
     });
   });
 });
diff --git a/website/src/controllers/api-v3/chat.js b/website/src/controllers/api-v3/chat.js
index d8b79b3979..7fc6f7deda 100644
--- a/website/src/controllers/api-v3/chat.js
+++ b/website/src/controllers/api-v3/chat.js
@@ -1,10 +1,13 @@
 import { authWithHeaders } from '../../middlewares/api-v3/auth';
 import cron from '../../middlewares/api-v3/cron';
 import { model as Group } from '../../models/group';
+import { model as User } from '../../models/user';
 import {
   NotFound,
 } from '../../libs/api-v3/errors';
 import _ from 'lodash';
+import { sendTxn } from '../../libs/api-v3/email';
+import nconf    from 'nconf';
 
 let api = {};
 
@@ -137,10 +140,140 @@ api.likeChat = {
         message.likes[user._id] = true;
       }
 
-      return group.save();
+      return Group.update(
+        {_id: group._id, 'chat.id': message.id},
+        {$set: {'chat.$.likes': message.likes}}
+      );
     })
-    .then((group) => {
-      if (!group) throw new NotFound(res.t('groupNotFound'));
+    .then((groupSaved) => {
+      if (!groupSaved) throw new NotFound(res.t('groupNotFound'));
+      res.respond(200, message);
+    })
+    .catch(next);
+  },
+};
+
+/**
+ * @api {post} /groups/:groupId/chat/:chatId/like Like a group chat message
+ * @apiVersion 3.0.0
+ * @apiName LikeChat
+ * @apiGroup Chat
+ *
+ * @apiParam {groupId} groupId The group _id
+ * @apiParam {chatId} chatId The chat message _id
+ *
+ * @apiSuccess {Array} chat An array of chat messages
+ */
+api.flagChat = {
+  method: 'Post',
+  url: '/groups/:groupId/chat/:chatId/flag',
+  middlewares: [authWithHeaders(), cron],
+  handler (req, res, next) {
+    let user = res.locals.user;
+    let groupId = req.params.groupId;
+    let message;
+    let group;
+    let author;
+
+    req.checkParams('groupId', res.t('groupIdRequired')).notEmpty();
+    req.checkParams('chatId', res.t('chatIdRequired')).notEmpty();
+
+    let validationErrors = req.validationErrors();
+    if (validationErrors) return next(validationErrors);
+
+    Group.getGroup(user, groupId)
+    .then((groupFound) => {
+      if (!groupFound) throw new NotFound(res.t('groupNotFound'));
+      group = groupFound;
+      message = _.find(group.chat, {id: req.params.chatId});
+
+      if (!message) throw new NotFound(res.t('messageGroupChatNotFound'));
+
+      if (message.uuid === user._id) throw new NotFound(res.t('messageGroupChatFlagOwnMessage'));
+
+      return User.findOne({_id: message.uuid}, {auth: 1});
+    })
+    .then((foundAuthor) => {
+      author = foundAuthor;
+
+      // Log user ids that have flagged the message
+      if (!message.flags) message.flags = {};
+      if (message.flags[user._id] && !user.contributor.admin) throw new NotFound(res.t('messageGroupChatFlagAlreadyReported'));
+      message.flags[user._id] = true;
+
+      // Log total number of flags (publicly viewable)
+      if (!message.flagCount) message.flagCount = 0;
+      if (user.contributor.admin) {
+        // Arbitraty amount, higher than 2
+        message.flagCount = 5;
+      } else {
+        message.flagCount++;
+      }
+
+      // return group.save();
+      return Group.update(
+        {_id: group._id, 'chat.id': message.id},
+        {$set: {
+          'chat.$.flags': message.flags,
+          'chat.$.flagCount': message.flagCount,
+        }});
+    })
+    .then((group2) => {
+      if (!group2) throw new NotFound(res.t('groupNotFound'));
+
+      let addressesToSendTo = nconf.get('FLAG_REPORT_EMAIL');
+      addressesToSendTo = typeof addressesToSendTo === 'string' ? JSON.parse(addressesToSendTo) : addressesToSendTo;
+
+      if (Array.isArray(addressesToSendTo)) {
+        addressesToSendTo = addressesToSendTo.map((email) => {
+          return {email, canSend: true};
+        });
+      } else {
+        addressesToSendTo = {email: addressesToSendTo};
+      }
+
+      let reporterEmailContent;
+      if (user.auth.local) {
+        reporterEmailContent = user.auth.local.email;
+      } else if (user.auth.facebook && user.auth.facebook.emails && user.auth.facebook.emails[0]) {
+        reporterEmailContent = user.auth.facebook.emails[0].value;
+      }
+
+      let authorEmailContent;
+      if (author.auth.local) {
+        authorEmailContent = author.auth.local.email;
+      } else if (author.auth.facebook && author.auth.facebook.emails && author.auth.facebook.emails[0]) {
+        authorEmailContent = author.auth.facebook.emails[0].value;
+      }
+
+      let groupUrl;
+      if (group._id === 'habitrpg') {
+        groupUrl = '/#/options/groups/tavern';
+      } else if (group.type === 'guild') {
+        groupUrl = `/#/options/groups/guilds/{$group._id}`;
+      } else {
+        groupUrl = 'party';
+      }
+
+      sendTxn(addressesToSendTo, 'flag-report-to-mods', [
+        {name: 'MESSAGE_TIME', content: (new Date(message.timestamp)).toString()},
+        {name: 'MESSAGE_TEXT', content: message.text},
+
+        {name: 'REPORTER_USERNAME', content: user.profile.name},
+        {name: 'REPORTER_UUID', content: user._id},
+        {name: 'REPORTER_EMAIL', content: reporterEmailContent},
+        {name: 'REPORTER_MODAL_URL', content: `/static/front/#?memberId={$user._id}`},
+
+        {name: 'AUTHOR_USERNAME', content: message.user},
+        {name: 'AUTHOR_UUID', content: message.uuid},
+        {name: 'AUTHOR_EMAIL', content: authorEmailContent},
+        {name: 'AUTHOR_MODAL_URL', content: `/static/front/#?memberId={$message.uuid}`},
+
+        {name: 'GROUP_NAME', content: group.name},
+        {name: 'GROUP_TYPE', content: group.type},
+        {name: 'GROUP_ID', content: group._id},
+        {name: 'GROUP_URL', content: groupUrl},
+      ]);
       res.respond(200, message);
     })
     .catch(next);