diff --git a/app/soapbox/features/chats/chat_room.js b/app/soapbox/features/chats/chat_room.js
index e6df1953d..4a8c480ea 100644
--- a/app/soapbox/features/chats/chat_room.js
+++ b/app/soapbox/features/chats/chat_room.js
@@ -6,18 +6,20 @@ import { injectIntl } from 'react-intl';
 import ImmutablePureComponent from 'react-immutable-pure-component';
 import Avatar from 'soapbox/components/avatar';
 import { acctFull } from 'soapbox/utils/accounts';
-import { fetchChat } from 'soapbox/actions/chats';
+import { fetchChat, markChatRead } from 'soapbox/actions/chats';
 import ChatBox from './components/chat_box';
 import Column from 'soapbox/components/column';
 import ColumnBackButton from 'soapbox/components/column_back_button';
+import { Map as ImmutableMap } from 'immutable';
 import { makeGetChat } from 'soapbox/selectors';
 
 const mapStateToProps = (state, { params }) => {
   const getChat = makeGetChat();
+  const chat = state.getIn(['chats', params.chatId], ImmutableMap()).toJS();
 
   return {
     me: state.get('me'),
-    chat: getChat(state, { id: params.chatId }),
+    chat: getChat(state, chat),
   };
 };
 
@@ -42,9 +44,26 @@ class ChatRoom extends ImmutablePureComponent {
     this.inputElem.focus();
   }
 
+  markRead = () => {
+    const { dispatch, chat } = this.props;
+    if (!chat) return;
+    dispatch(markChatRead(chat.get('id')));
+  }
+
   componentDidMount() {
     const { dispatch, params } = this.props;
     dispatch(fetchChat(params.chatId));
+    this.markRead();
+  }
+
+  componentDidUpdate(prevProps) {
+    const markReadConditions = [
+      () => this.props.chat !== undefined,
+      () => this.props.chat.get('unread') > 0,
+    ];
+
+    if (markReadConditions.every(c => c() === true))
+      this.markRead();
   }
 
   render() {
diff --git a/app/soapbox/features/chats/components/chat_box.js b/app/soapbox/features/chats/components/chat_box.js
index 0f1de7dbb..40123ca25 100644
--- a/app/soapbox/features/chats/components/chat_box.js
+++ b/app/soapbox/features/chats/components/chat_box.js
@@ -40,11 +40,24 @@ class ChatBox extends ImmutablePureComponent {
     content: '',
   }
 
-  handleKeyDown = (e) => {
+  sendMessage = () => {
     const { chatId } = this.props;
-    if (e.key === 'Enter') {
-      this.props.dispatch(sendChatMessage(chatId, this.state));
-      this.setState({ content: '' });
+    if (this.state.content.length < 1) return;
+    this.props.dispatch(sendChatMessage(chatId, this.state));
+    this.setState({ content: '' });
+  }
+
+  insertLine = () => {
+    const { content } = this.state;
+    this.setState({ content: content + '\n' });
+  }
+
+  handleKeyDown = (e) => {
+    if (e.key === 'Enter' && e.shiftKey) {
+      this.insertLine();
+      e.preventDefault();
+    } else if (e.key === 'Enter') {
+      this.sendMessage();
       e.preventDefault();
     }
   }
diff --git a/app/soapbox/features/chats/components/chat_list.js b/app/soapbox/features/chats/components/chat_list.js
index 41aae6397..e24d31ab9 100644
--- a/app/soapbox/features/chats/components/chat_list.js
+++ b/app/soapbox/features/chats/components/chat_list.js
@@ -3,7 +3,6 @@ import { connect } from 'react-redux';
 import PropTypes from 'prop-types';
 import { injectIntl } from 'react-intl';
 import ImmutablePureComponent from 'react-immutable-pure-component';
-import { fetchChats } from 'soapbox/actions/chats';
 import Chat from './chat';
 import { makeGetChat } from 'soapbox/selectors';
 
@@ -42,10 +41,6 @@ class ChatList extends ImmutablePureComponent {
     emptyMessage: PropTypes.node,
   };
 
-  componentDidMount() {
-    this.props.dispatch(fetchChats());
-  }
-
   render() {
     const { chats, emptyMessage } = this.props;
 
diff --git a/app/soapbox/features/chats/components/chat_message_list.js b/app/soapbox/features/chats/components/chat_message_list.js
index 8e52e3270..e2fe305bd 100644
--- a/app/soapbox/features/chats/components/chat_message_list.js
+++ b/app/soapbox/features/chats/components/chat_message_list.js
@@ -4,9 +4,14 @@ import PropTypes from 'prop-types';
 import ImmutablePropTypes from 'react-immutable-proptypes';
 import { injectIntl } from 'react-intl';
 import ImmutablePureComponent from 'react-immutable-pure-component';
-import { List as ImmutableList } from 'immutable';
+import { Map as ImmutableMap, List as ImmutableList } from 'immutable';
 import emojify from 'soapbox/features/emoji/emoji';
 import classNames from 'classnames';
+import { escape } from 'lodash';
+
+const makeEmojiMap = record => record.get('emojis', ImmutableList()).reduce((map, emoji) => {
+  return map.set(`:${emoji.get('shortcode')}:`, emoji);
+}, ImmutableMap());
 
 const mapStateToProps = (state, { chatMessageIds }) => ({
   me: state.get('me'),
@@ -72,6 +77,18 @@ class ChatMessageList extends ImmutablePureComponent {
       this.scrollToBottom();
   }
 
+  parsePendingContent = content => {
+    return escape(content).replace(/(?:\r\n|\r|\n)/g, '<br>');
+  }
+
+  parseContent = chatMessage => {
+    const content = chatMessage.get('content') || '';
+    const pending = chatMessage.get('pending', false);
+    const formatted = pending ? this.parsePendingContent(content) : content;
+    const emojiMap = makeEmojiMap(chatMessage);
+    return emojify(formatted, emojiMap.toJS());
+  }
+
   render() {
     const { chatMessages, me } = this.props;
 
@@ -88,7 +105,7 @@ class ChatMessageList extends ImmutablePureComponent {
             <span
               title={this.getFormattedTimestamp(chatMessage)}
               className='chat-message__bubble'
-              dangerouslySetInnerHTML={{ __html: emojify(chatMessage.get('content') || '') }}
+              dangerouslySetInnerHTML={{ __html: this.parseContent(chatMessage) }}
               ref={this.setRef}
             />
           </div>
diff --git a/app/soapbox/features/ui/index.js b/app/soapbox/features/ui/index.js
index 59269d577..ff80086ee 100644
--- a/app/soapbox/features/ui/index.js
+++ b/app/soapbox/features/ui/index.js
@@ -18,6 +18,7 @@ import { expandHomeTimeline } from '../../actions/timelines';
 import { expandNotifications } from '../../actions/notifications';
 import { fetchReports } from '../../actions/admin';
 import { fetchFilters } from '../../actions/filters';
+import { fetchChats } from 'soapbox/actions/chats';
 import { clearHeight } from '../../actions/height_cache';
 import { openModal } from '../../actions/modal';
 import { WrappedRoute } from './util/react_router_helpers';
@@ -433,6 +434,7 @@ class UI extends React.PureComponent {
     if (account) {
       this.props.dispatch(expandHomeTimeline());
       this.props.dispatch(expandNotifications());
+      this.props.dispatch(fetchChats());
       // this.props.dispatch(fetchGroups('member'));
       if (isStaff(account))
         this.props.dispatch(fetchReports({ state: 'open' }));
diff --git a/app/styles/chats.scss b/app/styles/chats.scss
index 7ae51847d..011543ca3 100644
--- a/app/styles/chats.scss
+++ b/app/styles/chats.scss
@@ -113,6 +113,8 @@
     background-color: var(--background-color);
     overflow: hidden;
     text-overflow: ellipsis;
+    overflow-wrap: break-word;
+    white-space: break-spaces;
 
     a {
       color: var(--brand-color--hicontrast);