diff --git a/test/api/unit/models/group.test.js b/test/api/unit/models/group.test.js
index e2d54d8575..25083c2583 100644
--- a/test/api/unit/models/group.test.js
+++ b/test/api/unit/models/group.test.js
@@ -6,6 +6,8 @@ import {
   SPAM_MESSAGE_LIMIT,
   SPAM_MIN_EXEMPT_CONTRIB_LEVEL,
   SPAM_WINDOW_LENGTH,
+  MAX_CHAT_COUNT,
+  MAX_SUBBED_GROUP_CHAT_COUNT,
   INVITES_LIMIT,
   model as Group,
 } from '../../../../website/server/models/group';
@@ -18,6 +20,7 @@ import {
 import * as email from '../../../../website/server/libs/email';
 import { TAVERN_ID } from '../../../../website/common/script/constants';
 import shared from '../../../../website/common';
+import { chatModel as Chat } from '../../../../website/server/models/message';
 
 describe('Group Model', () => {
   let party; let questLeader; let participatingMember;
@@ -1356,6 +1359,29 @@ describe('Group Model', () => {
       });
     });
 
+    describe('#getEffectiveChatLimit', () => {
+      it('returns the correct chat limit', () => {
+        const group = new Group();
+        expect(group.getEffectiveChatLimit()).to.eql(MAX_CHAT_COUNT);
+      });
+
+      it('returns the passed limit if it is lower than the max', () => {
+        const group = new Group();
+        expect(group.getEffectiveChatLimit(10)).to.eql(10);
+      });
+
+      it('returns the max if the passed limit is higher', () => {
+        const group = new Group();
+        expect(group.getEffectiveChatLimit(MAX_CHAT_COUNT + 10)).to.eql(MAX_CHAT_COUNT);
+      });
+
+      it('returns the max for group plans', () => {
+        const group = new Group();
+        group.purchased.plan.customerId = '110002222333';
+        expect(group.getEffectiveChatLimit()).to.eql(MAX_SUBBED_GROUP_CHAT_COUNT);
+      });
+    });
+
     describe('#sendChat', () => {
       beforeEach(() => {
         sandbox.spy(User, 'updateOne');
@@ -1462,6 +1488,34 @@ describe('Group Model', () => {
       });
     });
 
+    describe('#trimChat', () => {
+      it('Only checks last message when not enough messages to trim', async () => {
+        sandbox.spy(Chat, 'find');
+        sandbox.spy(Chat, 'deleteMany');
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+        await party.trimChat();
+
+        expect(Chat.find).to.be.calledOnce;
+        expect(Chat.deleteMany).to.not.be.called;
+        expect(await Chat.countDocuments({ groupId: party._id })).to.eql(3);
+      });
+      it('Deletes messages over the limit', async () => {
+        sandbox.spy(Chat, 'find');
+        sandbox.spy(Chat, 'deleteMany');
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+        await Chat.insertOne({ groupId: party._id, timestamp: new Date() });
+
+        await party.trimChat(1);
+
+        expect(Chat.find).to.be.calledOnce;
+        expect(Chat.deleteMany).to.be.calledOnce;
+        expect(await Chat.countDocuments({ groupId: party._id })).to.eql(1);
+      });
+    });
+
     describe('#startQuest', () => {
       context('Failure Conditions', () => {
         it('throws an error if group is not a party', async () => {
diff --git a/website/server/controllers/api-v3/chat.js b/website/server/controllers/api-v3/chat.js
index 40ed380031..c50ae20366 100644
--- a/website/server/controllers/api-v3/chat.js
+++ b/website/server/controllers/api-v3/chat.js
@@ -227,6 +227,7 @@ api.postChat = {
     }
 
     await Promise.all(toSave);
+    await group.trimChat();
 
     if (chatUpdated) {
       res.respond(200, { chat: chatRes.chat });
diff --git a/website/server/libs/chat/group-chat.js b/website/server/libs/chat/group-chat.js
index 028f987b4a..1e0ca50fc0 100644
--- a/website/server/libs/chat/group-chat.js
+++ b/website/server/libs/chat/group-chat.js
@@ -1,25 +1,13 @@
 import _ from 'lodash';
 import { chatModel as Chat } from '../../models/message';
 import shared from '../../../common';
-import { // eslint-disable-line import/no-cycle
-  MAX_CHAT_COUNT,
-  MAX_SUBBED_GROUP_CHAT_COUNT,
-} from '../../models/group';
 
 const questScrolls = shared.content.quests;
 
 // @TODO: Don't use this method when the group can be saved.
 export async function getGroupChat (group, options = {}) {
   const { limit, before } = options;
-
-  let maxChatCount = MAX_CHAT_COUNT;
-  if (group.chatLimitCount && group.chatLimitCount >= MAX_CHAT_COUNT) {
-    maxChatCount = group.chatLimitCount;
-  } else if (group.hasActiveGroupPlan()) {
-    maxChatCount = MAX_SUBBED_GROUP_CHAT_COUNT;
-  }
-
-  const effectiveLimit = limit !== undefined ? Math.min(limit, maxChatCount) : maxChatCount;
+  const effectiveLimit = group.getEffectiveChatLimit(limit);
 
   let query = Chat.find({ groupId: group._id })
     .sort('-timestamp');
diff --git a/website/server/models/group.js b/website/server/models/group.js
index 2517d01162..845584b13b 100644
--- a/website/server/models/group.js
+++ b/website/server/models/group.js
@@ -497,6 +497,17 @@ schema.statics.validateInvitations = async function getInvitationErr (invites, r
   }
 };
 
+schema.methods.getEffectiveChatLimit = function getEffectiveChatLimit (limit) {
+  let maxChatCount = MAX_CHAT_COUNT;
+  if (this.chatLimitCount && this.chatLimitCount >= MAX_CHAT_COUNT) {
+    maxChatCount = this.chatLimitCount;
+  } else if (this.hasActiveGroupPlan()) {
+    maxChatCount = MAX_SUBBED_GROUP_CHAT_COUNT;
+  }
+
+  return limit !== undefined ? Math.min(limit, maxChatCount) : maxChatCount;
+};
+
 schema.methods.getParticipatingQuestMembers = function getParticipatingQuestMembers () {
   return Object.keys(this.quest.members).filter(member => this.quest.members[member]);
 };
@@ -654,6 +665,18 @@ schema.methods.sendChat = async function sendChat (options = {}) {
   return newChatMessage;
 };
 
+schema.methods.trimChat = async function trimChat (limit) {
+  const query = Chat.find({ groupId: this._id })
+    .sort('-timestamp')
+    .skip(limit || (this.getEffectiveChatLimit() * 2))
+    .limit(1);
+  const lastMessage = await query.exec();
+  if (lastMessage && lastMessage.length > 0) {
+    const lastMessageTimestamp = lastMessage[0].timestamp;
+    await Chat.deleteMany({ groupId: this._id, timestamp: { $lte: lastMessageTimestamp } }).exec();
+  }
+};
+
 // eslint-disable-next-line max-len
 schema.methods.handleQuestInvitation = async function handleQuestInvitation (user, accept, session) {
   if (!user) throw new InternalServerError('Must provide user to handle quest invitation');