diff --git a/src/components/MarkdownEditor.js b/src/components/MarkdownEditor.js
index aeac362f6..cf0a2736c 100644
--- a/src/components/MarkdownEditor.js
+++ b/src/components/MarkdownEditor.js
@@ -2,6 +2,8 @@ import React, { Component } from 'react';
 import PropTypes from 'prop-types';
 import SimpleMDE from 'simplemde';
 import hljs from '../utils/highlighter';
+import FilePicker from './FilePicker';
+import { getExtensionFromPath } from '../utils/helpers';
 
 const classNames = [
   'editor-toolbar',
@@ -38,6 +40,9 @@ class MarkdownEditor extends Component {
     opts['renderingConfig'] = {
       codeSyntaxHighlighting: true,
     };
+    opts['insertTexts'] = {
+      image: ['![', '](#url#)'],
+    };
     let toolbarIcons = [
       'bold',
       'italic',
@@ -51,6 +56,12 @@ class MarkdownEditor extends Component {
       'link',
       'image',
       'table',
+      {
+        name: 'filepicker',
+        action: () => this.refs.filepicker.refs.trigger.click(),
+        className: 'fa fa-paperclip',
+        title: 'Insert Static File',
+      },
       '|',
       'preview',
       'side-by-side',
@@ -84,11 +95,48 @@ class MarkdownEditor extends Component {
     }
   }
 
+  // Adapted from an internal helper function within SimpleMDE package.
+  _replaceSelectedText = (cm, headNTail, url) => {
+    const startPoint = cm.getCursor('start');
+    const endPoint = cm.getCursor('end');
+    const text = cm.getSelection();
+
+    let [head, tail] = headNTail;
+    if (url) {
+      tail = tail.replace('#url#', url);
+    }
+
+    cm.replaceSelection(`${head}${text}${tail}`);
+    startPoint.ch += head.length;
+
+    if (startPoint !== endPoint) {
+      endPoint.ch += head.length;
+    }
+
+    cm.setSelection(startPoint, endPoint);
+    cm.focus();
+  };
+
+  handleFilePick = path => {
+    const { codemirror, getState, options } = this.editor;
+    const { image, link } = options.insertTexts;
+    const url = `{{ '${path}' | relative_url }}`;
+    const ext = getExtensionFromPath(path);
+
+    const type = /png|jpg|gif|jpeg|svg|ico/i.test(ext) ? image : link;
+    this._replaceSelectedText(codemirror, type, url);
+  };
+
   render() {
-    return React.createElement(
-      'div',
-      { ref: 'container' },
-      React.createElement('textarea', { ref: 'text' })
+    return (
+      <div>
+        <div style={{ display: 'none' }}>
+          <FilePicker ref="filepicker" onPick={this.handleFilePick} />
+        </div>
+        <div ref="container">
+          <textarea ref="text" />
+        </div>
+      </div>
     );
   }
 }
diff --git a/src/components/tests/__snapshots__/markdowneditor.spec.js.snap b/src/components/tests/__snapshots__/markdowneditor.spec.js.snap
index 42b53a3c5..ea0c6bc54 100644
--- a/src/components/tests/__snapshots__/markdowneditor.spec.js.snap
+++ b/src/components/tests/__snapshots__/markdowneditor.spec.js.snap
@@ -2,6 +2,29 @@
 
 exports[`Components::MarkdownEditor renders correctly 1`] = `
 <div>
-  <textarea />
+  <div
+    style={
+      Object {
+        "display": "none",
+      }
+    }
+  >
+    <span
+      className="images-wrapper"
+    >
+      <button
+        onClick={[Function]}
+      >
+        <i
+          aria-hidden="true"
+          className="fa fa-picture-o"
+        />
+      </button>
+      <noscript />
+    </span>
+  </div>
+  <div>
+    <textarea />
+  </div>
 </div>
 `;
diff --git a/src/components/tests/markdowneditor.spec.js b/src/components/tests/markdowneditor.spec.js
index 3da7c5d14..8a50e0afa 100644
--- a/src/components/tests/markdowneditor.spec.js
+++ b/src/components/tests/markdowneditor.spec.js
@@ -1,7 +1,9 @@
 import React from 'react';
 import ReactDOM from 'react-dom';
 import renderer from 'react-test-renderer';
+import { mount } from 'enzyme';
 import MarkdownEditor from '../MarkdownEditor';
+import FilePicker from '../FilePicker';
 
 const props = {
   onChange: f => f,
@@ -10,12 +12,47 @@ const props = {
   initialValue: '',
 };
 
+function setup() {
+  const component = mount(<MarkdownEditor {...props} />);
+  const { editor } = component.nodes[0];
+  return {
+    component,
+    editor,
+    cm: editor.codemirror,
+  };
+}
+
 describe('Components::MarkdownEditor', () => {
   it('renders without crashing', () => {
     const div = document.createElement('div');
     ReactDOM.render(<MarkdownEditor {...props} />, div);
   });
 
+  it('allows selecting static-file', () => {
+    const { component, cm } = setup();
+
+    component.node._replaceSelectedText = jest.fn();
+    cm.replaceSelection = jest.fn();
+    cm.setSelection = jest.fn();
+    cm.focus = jest.fn();
+
+    const { _replaceSelectedText } = component.node;
+
+    component.find(FilePicker).prop('onPick')('foo.png');
+    expect(_replaceSelectedText).lastCalledWith(
+      cm,
+      ['![', '](#url#)', '![](', '#url#)'],
+      "{{ 'foo.png' | relative_url }}"
+    );
+
+    component.find(FilePicker).prop('onPick')('bar.txt');
+    expect(_replaceSelectedText).lastCalledWith(
+      cm,
+      ['[', '](#url#)'],
+      "{{ 'bar.txt' | relative_url }}"
+    );
+  });
+
   it('renders correctly', () => {
     const tree = renderer.create(<MarkdownEditor {...props} />).toJSON();
     expect(tree).toMatchSnapshot();