diff --git a/plugins/talk-plugin-rich-text/client/components/rte/RTE.js b/plugins/talk-plugin-rich-text/client/components/rte/RTE.js
index 55ce25333..422109292 100644
--- a/plugins/talk-plugin-rich-text/client/components/rte/RTE.js
+++ b/plugins/talk-plugin-rich-text/client/components/rte/RTE.js
@@ -3,17 +3,15 @@ import PropTypes from 'prop-types';
 import styles from './RTE.css';
 import cn from 'classnames';
 import ContentEditable from 'react-contenteditable';
-import Toolbar from './Toolbar';
+import Toolbar from './components/Toolbar';
+import { insertNewLine } from './lib/dom';
+import API from './lib/api';
 
-class Editor extends React.Component {
+class RTE extends React.Component {
   ref = null;
-  handleRef = ref => (this.ref = ref);
+  api = null;
   buttonsRef = {};
 
-  get contentEditable() {
-    return this.ref.htmlEl;
-  }
-
   createButtonRefHandler(key) {
     return ref => {
       if (ref) {
@@ -24,38 +22,46 @@ class Editor extends React.Component {
     };
   }
 
-  hasAncestor(tag) {
-    const sel = window.getSelection();
-    const range = sel.getRangeAt(0);
-    let cur = range.startContainer;
-    do {
-      if (cur.nodeName === tag) {
-        return true;
-      }
-      cur = cur.parentNode;
-    } while (cur);
-    return false;
-  }
-
   forEachButton(callback) {
     Object.keys(this.buttonsRef).map(k => callback(this.buttonsRef[k]));
   }
 
-  handleChange = evt => {
+  handleChange = () => {
     this.props.onChange({
       text: this.ref.htmlEl.innerText,
-      html: evt.target.value,
+      html: this.ref.htmlEl.innerHTML,
     });
   };
 
+  handleRef = ref => (
+    (this.ref = ref), (this.api = new API(this.ref.htmlEl, this.handleChange))
+  );
+
   handleSelectionChange = () => {
+    //  console.log(window.getSelection().getRangeAt(0));
     this.forEachButton(b => {
       b.onSelectionChange && b.onSelectionChange();
     });
   };
 
+  handleSpecialEnter = () => {
+    let handled = false;
+    const sel = window.getSelection();
+    const range = sel.getRangeAt(0);
+    let container = range.startContainer;
+    while (!handled && container && container !== this.ref.htmlEl) {
+      this.forEachButton(b => {
+        if (!handled) {
+          handled = !!(b.onEnter && b.onEnter(container));
+        }
+      });
+      container = container.parentNode;
+    }
+    return handled;
+  };
+
   handleClick = () => {
-    this.handleSelectionChange();
+    setTimeout(() => this.handleSelectionChange());
   };
 
   handleKeyDown = () => {
@@ -68,17 +74,25 @@ class Editor extends React.Component {
 
   handleKeyPress = e => {
     this.handleSelectionChange();
-    if (e.key === 'Enter' && !e.shiftKey) {
-      setTimeout(() => {
-        document.execCommand('outdent');
-      });
+    if (e.key === 'Enter') {
+      if (!e.shiftKey && this.handleSpecialEnter()) {
+        this.handleChange();
+        e.preventDefault();
+        return false;
+      }
+
+      insertNewLine(true);
+
+      this.handleChange();
+      e.preventDefault();
+      return false;
     }
   };
 
   renderButtons() {
     return this.props.buttons.map(b => {
       return React.cloneElement(b, {
-        rte: this,
+        api: this.api,
         ref: this.createButtonRefHandler(b.key),
       });
     });
@@ -115,11 +129,11 @@ class Editor extends React.Component {
   }
 }
 
-Editor.defaultProps = {
+RTE.defaultProps = {
   buttons: [],
 };
 
-Editor.propTypes = {
+RTE.propTypes = {
   buttons: PropTypes.array,
   inputId: PropTypes.string,
   input: PropTypes.object,
@@ -132,4 +146,4 @@ Editor.propTypes = {
   value: PropTypes.string,
 };
 
-export default Editor;
+export default RTE;
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/buttons/Blockquote.js b/plugins/talk-plugin-rich-text/client/components/rte/buttons/Blockquote.js
index 1ba9d933f..7d3b76d6f 100644
--- a/plugins/talk-plugin-rich-text/client/components/rte/buttons/Blockquote.js
+++ b/plugins/talk-plugin-rich-text/client/components/rte/buttons/Blockquote.js
@@ -1,24 +1,58 @@
 import createToggle from '../factories/createToggle';
-import { hasAncestor } from '../utils';
-import bowser from 'bowser';
+import {
+  findIntersectingTag,
+  insertNewLineAfterNode,
+  replaceSelection,
+  insertNodes,
+  getSelectedNodesExpanded,
+  outdentNode,
+} from '../lib/dom';
 
-const execCommand = () => {
-  if (hasAncestor('BLOCKQUOTE')) {
-    document.execCommand('outdent');
+// TODO: select end of node.
+function selectNode(node) {
+  const range = document.createRange();
+  const container = node.childNodes.length ? node.childNodes[0] : node;
+  range.setStart(container, 0);
+  range.setEnd(container, 0);
+  replaceSelection(range);
+}
+
+function execCommand() {
+  const bq = findIntersectingTag('BLOCKQUOTE');
+  if (bq) {
+    outdentNode(bq, true);
   } else {
-    if (bowser.msie) {
-      document.execCommand('indent');
+    const node = document.createElement('blockquote');
+    const selectedNodes = getSelectedNodesExpanded();
+    if (selectedNodes.length) {
+      const firstNode = selectedNodes[0];
+      firstNode.parentNode.insertBefore(node, firstNode);
+      selectedNodes.forEach(n => {
+        node.appendChild(n);
+      });
+      selectNode(node);
     } else {
-      document.execCommand('formatBlock', false, 'blockquote');
+      node.appendChild(document.createElement('br'));
+      insertNodes(node);
+      selectNode(node);
     }
+    this.broadcastChange();
   }
+}
+
+function syncState() {
+  return !!findIntersectingTag('BLOCKQUOTE');
+}
+
+const onEnter = node => {
+  if (node.tagName !== 'BLOCKQUOTE') {
+    return;
+  }
+  insertNewLineAfterNode(node, true);
+  return true;
 };
 
-const syncState = () => {
-  return hasAncestor('BLOCKQUOTE');
-};
-
-const Blockquote = createToggle(execCommand, syncState);
+const Blockquote = createToggle(execCommand, syncState, { onEnter });
 
 Blockquote.defaultProps = {
   children: 'Blockquote',
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/Button.css b/plugins/talk-plugin-rich-text/client/components/rte/components/Button.css
similarity index 100%
rename from plugins/talk-plugin-rich-text/client/components/rte/Button.css
rename to plugins/talk-plugin-rich-text/client/components/rte/components/Button.css
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/Button.js b/plugins/talk-plugin-rich-text/client/components/rte/components/Button.js
similarity index 100%
rename from plugins/talk-plugin-rich-text/client/components/rte/Button.js
rename to plugins/talk-plugin-rich-text/client/components/rte/components/Button.js
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/Toolbar.css b/plugins/talk-plugin-rich-text/client/components/rte/components/Toolbar.css
similarity index 100%
rename from plugins/talk-plugin-rich-text/client/components/rte/Toolbar.css
rename to plugins/talk-plugin-rich-text/client/components/rte/components/Toolbar.css
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/Toolbar.js b/plugins/talk-plugin-rich-text/client/components/rte/components/Toolbar.js
similarity index 100%
rename from plugins/talk-plugin-rich-text/client/components/rte/Toolbar.js
rename to plugins/talk-plugin-rich-text/client/components/rte/components/Toolbar.js
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/factories/createToggle.js b/plugins/talk-plugin-rich-text/client/components/rte/factories/createToggle.js
index 61c7263a3..040dc6543 100644
--- a/plugins/talk-plugin-rich-text/client/components/rte/factories/createToggle.js
+++ b/plugins/talk-plugin-rich-text/client/components/rte/factories/createToggle.js
@@ -1,25 +1,29 @@
 import React from 'react';
 import PropTypes from 'prop-types';
-import Button from '../Button';
+import Button from '../components/Button';
 
-const createToggle = (execCommand, getCurrentState) => {
+const createToggle = (execCommand, getCurrentState, { onEnter } = {}) => {
   class Toggle extends React.Component {
     state = {
       active: false,
     };
 
+    execCommand = () => execCommand.apply(this.props.api);
+    getCurrentState = () => getCurrentState.apply(this.props.api);
+    onEnter = (...args) => onEnter && onEnter.apply(this.props.api, args);
+
     formatToggle = () => {
-      execCommand();
-      this.props.rte.contentEditable.focus();
+      this.execCommand();
     };
 
     handleClick = () => {
+      this.props.api.focus();
       this.formatToggle();
-      this.syncState();
+      this.props.api.focus();
     };
 
     syncState = () => {
-      if (this.state.active !== getCurrentState()) {
+      if (this.state.active !== this.getCurrentState()) {
         this.setState(state => ({
           active: !state.active,
         }));
@@ -46,7 +50,7 @@ const createToggle = (execCommand, getCurrentState) => {
   }
 
   Toggle.propTypes = {
-    rte: PropTypes.object,
+    api: PropTypes.object,
     className: PropTypes.string,
     title: PropTypes.string,
     children: PropTypes.node,
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/lib/api.js b/plugins/talk-plugin-rich-text/client/components/rte/lib/api.js
new file mode 100644
index 000000000..5150753d2
--- /dev/null
+++ b/plugins/talk-plugin-rich-text/client/components/rte/lib/api.js
@@ -0,0 +1,14 @@
+import { selectionIsInside } from './dom';
+
+export default class API {
+  constructor(contentEditable, onChange) {
+    this.contentEditable = contentEditable;
+    this.broadcastChange = onChange;
+  }
+  isSelectionInside() {
+    return selectionIsInside(this.contentEditable);
+  }
+  focus() {
+    this.contentEditable.focus();
+  }
+}
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/lib/dom.js b/plugins/talk-plugin-rich-text/client/components/rte/lib/dom.js
new file mode 100644
index 000000000..24a22f317
--- /dev/null
+++ b/plugins/talk-plugin-rich-text/client/components/rte/lib/dom.js
@@ -0,0 +1,333 @@
+export function findAncestorWithTag(node, tag) {
+  do {
+    if (node.nodeName === tag) {
+      return node;
+    }
+    node = node.parentNode;
+  } while (node);
+  return false;
+}
+
+export function findIntersectingTag(tag) {
+  const range = getSelectionRange();
+  if (!range) {
+    return null;
+  }
+
+  const ancestor = findAncestorWithTag(range.startContainer, tag);
+  if (ancestor) {
+    return ancestor;
+  }
+
+  const nodes = getSelectedChildren(range.commonAncestorContainer);
+  for (let i = 0; i < nodes.length; i++) {
+    if (nodes[i].tagName === tag) {
+      return nodes[i];
+    }
+    const query = nodes[i].querySelector && nodes[i].querySelector(tag);
+    if (query) {
+      return query;
+    }
+  }
+  return null;
+}
+
+export function indexOfChildNode(parent, child) {
+  for (let i = 0; i < parent.childNodes.length; i++) {
+    if (parent.childNodes[i] === child) {
+      return i;
+    }
+  }
+  return -1;
+}
+
+export function insertText(text) {
+  const selection = window.getSelection();
+  if (!selection.isCollapsed) {
+    document.execCommand('delete');
+  }
+  const range = selection.getRangeAt(0);
+  const offset = range.startOffset;
+  const container = range.startContainer;
+
+  if (container.nodeName === '#text') {
+    container.textContent =
+      container.textContent.slice(0, offset) +
+      text +
+      container.textContent.slice(offset);
+    const nextOffset = offset + text.length;
+    range.setStart(container, nextOffset);
+    range.setEnd(container, nextOffset);
+  } else {
+    const textNode = document.createTextNode(text);
+    container.insertBefore(textNode, container.childNodes[offset]);
+  }
+}
+
+export function insertNodes(...nodes) {
+  const selection = window.getSelection();
+  if (!selection.isCollapsed) {
+    document.execCommand('delete');
+  }
+  const range = selection.getRangeAt(0);
+  const offset = range.startOffset;
+  const container = range.startContainer;
+  if (container.nodeName === '#text') {
+    const startSlice = container.textContent.slice(0, offset);
+    const endSlice = container.textContent.slice(offset);
+    if (startSlice) {
+      nodes.splice(0, 0, document.createTextNode(startSlice));
+    }
+    if (endSlice) {
+      nodes.push(document.createTextNode(endSlice));
+    }
+    const parentNode = container.parentNode;
+    nodes.forEach(n => parentNode.insertBefore(n, container));
+    parentNode.removeChild(container);
+  } else {
+    let parentNode = container;
+    let nextSibling = container.childNodes[offset];
+    nodes.forEach(n => parentNode.insertBefore(n, nextSibling));
+  }
+}
+
+export function replaceSelection(range) {
+  const selection = window.getSelection();
+  selection.removeAllRanges();
+  selection.addRange(range);
+}
+
+export function isSelectionCollapsed() {
+  return window.getSelection().isCollapsed;
+}
+
+export function getSelectionRange() {
+  const selection = window.getSelection();
+  return selection.rangeCount ? selection.getRangeAt(0) : null;
+}
+
+function ensureEndMarker(node) {
+  if (
+    !node.lastChild ||
+    node.lastChild.tagName !== 'BR' ||
+    node.lastChild.className !== 'coral-rte-end-marker'
+  ) {
+    const br = document.createElement('br');
+    br.className = 'coral-rte-end-marker';
+    node.appendChild(br);
+  }
+}
+
+export function selectionIsInside(node) {
+  const range = getSelectionRange();
+  return (
+    range &&
+    (node.contains(range.startContainer) || node.contains(range.endContainer))
+  );
+}
+
+export function appendNewLine(node, changeSelection) {
+  const el = document.createElement('br');
+  node.appendChild(el);
+
+  if (changeSelection) {
+    const offset = indexOfChildNode(node, el);
+    const range = document.createRange();
+    range.setStart(node, offset);
+    range.setEnd(node, offset);
+    replaceSelection(range);
+  }
+}
+
+export function insertNewLine(changeSelection) {
+  // Insert <br> node.
+  const el = document.createElement('br');
+  insertNodes(el);
+
+  // Calculate next selection.
+  const range = document.createRange();
+  if (el.nextSibling) {
+    const offset = indexOfChildNode(el.parentNode, el.nextSibling);
+    range.setStart(el.parentNode, offset);
+    range.setEnd(el.parentNode, offset);
+  } else {
+    // We need to add a <br> marker at the end, because we can't
+    // select the last <br>.
+    ensureEndMarker(el.parentNode);
+
+    const offset = el.parentNode.childNodes.length - 1;
+    range.setStart(el.parentNode, offset);
+    range.setEnd(el.parentNode, offset);
+  }
+
+  if (changeSelection) {
+    replaceSelection(range);
+  }
+}
+
+export function insertNewLineAfterNode(node, changeSelection) {
+  if (node.parentNode.lastChild === node) {
+    appendNewLine(node.parentNode, changeSelection);
+  } else {
+    if (changeSelection) {
+      const offset = indexOfChildNode(node.parentNode, node) + 1;
+      const range = document.createRange();
+      range.setStart(node.parentNode, offset);
+      range.setEnd(node.parentNode, offset);
+      replaceSelection(range);
+    }
+    insertNewLine();
+  }
+}
+
+export function getSelectedNode(container, offset) {
+  if (container.nodeName === '#text') {
+    return container;
+  }
+  return container.childNodes[offset];
+}
+
+export function isBlockElement(node) {
+  if (node.nodeName === '#text') {
+    return false;
+  }
+  return !window
+    .getComputedStyle(node)
+    .getPropertyValue('display')
+    .startsWith('inline');
+}
+
+export function findParentBlock(node) {
+  if (!node.parentNode) {
+    return null;
+  }
+  if (isBlockElement(node.parentNode)) {
+    return node.parentNode;
+  }
+  return findParentBlock(node.parentNode);
+}
+
+export function lastParentBeforeBlock(node) {
+  let child = node;
+  while (!isBlockElement(child.parentNode)) {
+    child = node.parentNode;
+  }
+  return child;
+}
+
+export function getLeftOfNode(node) {
+  let result = [];
+  let leftMost = node;
+  while (
+    leftMost.previousSibling &&
+    leftMost.previousSibling.tagName !== 'BR' &&
+    !isBlockElement(leftMost.previousSibling)
+  ) {
+    result.splice(0, 0, leftMost.previousSibling);
+    leftMost = leftMost.previousSibling;
+  }
+  return result;
+}
+
+export function getRightOfNode(node) {
+  let result = [];
+  let cur = node;
+  while (
+    cur.nextSibling &&
+    cur.nextSibling.tagName !== 'BR' &&
+    !isBlockElement(cur.nextSibling)
+  ) {
+    cur = cur.nextSibling;
+    result.push(cur);
+  }
+  if (cur.nextSibling && cur.nextSibling.tagName === 'BR') {
+    result.push(cur.nextSibling);
+  }
+  return result;
+}
+
+export function getWholeLine(node) {
+  if (isBlockElement(node)) {
+    return [node];
+  }
+  const child = lastParentBeforeBlock(node);
+  return [...getLeftOfNode(child), child, ...getRightOfNode(child)];
+}
+
+export function getSelectedLine() {
+  const range = getSelectionRange();
+  if (!range) {
+    return [];
+  }
+  const start = getSelectedNode(range.startContainer, range.startOffset);
+  return start ? getWholeLine(start) : [];
+}
+
+export function getSelectedNodesExpanded() {
+  const range = getSelectionRange();
+  if (!range) {
+    return [];
+  }
+
+  if (range.collapsed) {
+    return getSelectedLine();
+  }
+
+  let ancestor = range.commonAncestorContainer;
+  if (!isBlockElement(ancestor)) {
+    ancestor = findParentBlock(ancestor);
+  }
+
+  const result = getSelectedChildren(ancestor);
+  return [
+    ...getLeftOfNode(result[0]),
+    ...result,
+    ...getRightOfNode(result[result.length - 1]),
+  ];
+}
+
+export function getSelectedChildren(ancestor) {
+  const result = [];
+  const range = getSelectionRange();
+  if (!range) {
+    return result;
+  }
+  if (!range) {
+    return result;
+  }
+
+  const start = getSelectedNode(range.startContainer, range.startOffset);
+  const end = getSelectedNode(range.endContainer, range.endOffset);
+  let foundStart = false;
+  for (let i = 0; i < ancestor.childNodes.length; i++) {
+    const node = ancestor.childNodes[i];
+    if (!foundStart) {
+      if (node.contains(start)) {
+        foundStart = true;
+      }
+    }
+    if (foundStart) {
+      result.push(node);
+      if (node.contains(end)) {
+        break;
+      }
+    }
+  }
+  return result;
+}
+
+export function outdentNode(node, changeSelection) {
+  const parentNode = node.parentNode;
+  const offset = indexOfChildNode(parentNode, node);
+  while (node.childNodes.length) {
+    parentNode.insertBefore(node.childNodes[0], node);
+  }
+  parentNode.removeChild(node);
+
+  if (changeSelection) {
+    const range = document.createRange();
+    range.setStart(parentNode, offset);
+    range.setEnd(parentNode, offset);
+    replaceSelection(range);
+  }
+}
diff --git a/plugins/talk-plugin-rich-text/client/components/rte/utils.js b/plugins/talk-plugin-rich-text/client/components/rte/utils.js
deleted file mode 100644
index 0d613df8a..000000000
--- a/plugins/talk-plugin-rich-text/client/components/rte/utils.js
+++ /dev/null
@@ -1,12 +0,0 @@
-export function hasAncestor(tag) {
-  const sel = window.getSelection();
-  const range = sel.getRangeAt(0);
-  let cur = range.startContainer;
-  do {
-    if (cur.nodeName === tag) {
-      return true;
-    }
-    cur = cur.parentNode;
-  } while (cur);
-  return false;
-}