diff --git a/src/js/editor/editor.js b/src/js/editor/editor.js
index 3b0ab621b..82f5b26f7 100644
--- a/src/js/editor/editor.js
+++ b/src/js/editor/editor.js
@@ -26,7 +26,7 @@ import {
   DEFAULT_TEXT_EXPANSIONS, findExpansion, validateExpansion
 } from './text-expansions';
 import {
-  DEFAULT_KEY_COMMANDS, findKeyCommand, validateKeyCommand
+  DEFAULT_KEY_COMMANDS, findKeyCommands, validateKeyCommand
 } from './key-commands';
 import { capitalize } from '../utils/string-utils';
 import LifecycleCallbacksMixin from '../utils/lifecycle-callbacks';
@@ -196,7 +196,7 @@ class Editor {
     if (!validateKeyCommand(keyCommand)) {
       throw new Error('Key Command is not valid');
     }
-    this.keyCommands.push(keyCommand);
+    this.keyCommands.unshift(keyCommand);
   }
 
   handleExpansion(event) {
@@ -602,11 +602,27 @@ class Editor {
     this.handleKeyCommand(event);
   }
 
+  /**
+   * Finds and runs the first matching key command for the event
+   *
+   * If multiple commands are bound to a key combination, the
+   * first matching one is run.
+   *
+   * If a command returns `false` then the next matching command
+   * is run instead.
+   *
+   * @method handleKeyCommand
+   * @param {Event} event The keyboard event triggered by the user
+   * @private
+   */
   handleKeyCommand(event) {
-    const keyCommand = findKeyCommand(this.keyCommands, event);
-    if (keyCommand) {
-      event.preventDefault();
-      keyCommand.run(this);
+    const keyCommands = findKeyCommands(this.keyCommands, event);
+    for (let i=0; i<keyCommands.length; i++) {
+      let keyCommand = keyCommands[i];
+      if (keyCommand.run(this) !== false) {
+        event.preventDefault();
+        return;
+      }
     }
   }
 
diff --git a/src/js/editor/key-commands.js b/src/js/editor/key-commands.js
index 7de7e6cdc..d84040e55 100644
--- a/src/js/editor/key-commands.js
+++ b/src/js/editor/key-commands.js
@@ -1,6 +1,6 @@
 import Key from '../utils/key';
 import { MODIFIERS } from '../utils/key';
-import { detect } from '../utils/array-utils';
+import { filter } from '../utils/array-utils';
 import LinkCommand from '../commands/link';
 
 export const DEFAULT_KEY_COMMANDS = [{
@@ -50,10 +50,10 @@ export function validateKeyCommand(keyCommand) {
   return !!keyCommand.modifier && !!keyCommand.str && !!keyCommand.run;
 }
 
-export function findKeyCommand(keyCommands, keyEvent) {
+export function findKeyCommands(keyCommands, keyEvent) {
   const key = Key.fromEvent(keyEvent);
 
-  return detect(keyCommands, ({modifier, str}) => {
+  return filter(keyCommands, ({modifier, str}) => {
     return key.hasModifier(modifier) && key.isChar(str);
   });
 }
diff --git a/tests/acceptance/editor-key-commands-test.js b/tests/acceptance/editor-key-commands-test.js
index 29c59db11..ae1246984 100644
--- a/tests/acceptance/editor-key-commands-test.js
+++ b/tests/acceptance/editor-key-commands-test.js
@@ -72,3 +72,59 @@ test('new key commands can be registered', (assert) => {
 
   assert.ok(!!passedEditor && passedEditor === editor, 'run method is called');
 });
+
+test('duplicate key commands can be registered with the last registered winning', (assert) => {
+  const mobiledoc = Helpers.mobiledoc.build(
+    ({post, markupSection, marker}) => post([
+      markupSection('p', [marker('something')])
+    ]));
+
+  let firstCommandRan, secondCommandRan;
+  editor = new Editor({mobiledoc});
+  editor.registerKeyCommand({
+    modifier: MODIFIERS.CTRL,
+    str: 'X',
+    run() { firstCommandRan = true; }
+  });
+  editor.registerKeyCommand({
+    modifier: MODIFIERS.CTRL,
+    str: 'X',
+    run() { secondCommandRan = true; }
+  });
+  editor.render(editorElement);
+
+  Helpers.dom.triggerKeyCommand(editor, 'X', MODIFIERS.CTRL);
+
+  assert.ok(!firstCommandRan, 'first registered method not called');
+  assert.ok(!!secondCommandRan, 'last registered method is called');
+});
+
+test('returning false from key command causes next match to run', (assert) => {
+  const mobiledoc = Helpers.mobiledoc.build(
+    ({post, markupSection, marker}) => post([
+      markupSection('p', [marker('something')])
+    ]));
+
+  let firstCommandRan, secondCommandRan;
+  editor = new Editor({mobiledoc});
+  editor.registerKeyCommand({
+    modifier: MODIFIERS.CTRL,
+    str: 'X',
+    run() { firstCommandRan = true; }
+  });
+  editor.registerKeyCommand({
+    modifier: MODIFIERS.CTRL,
+    str: 'X',
+    run() {
+      secondCommandRan = true;
+      return false;
+    }
+  });
+  editor.render(editorElement);
+
+  Helpers.dom.triggerKeyCommand(editor, 'X', MODIFIERS.CTRL);
+
+  assert.ok(!!secondCommandRan, 'last registered method is called');
+  assert.ok(!!firstCommandRan, 'first registered method is called');
+});
+