Category Archives: gmail-Crypt

Mymail-Crypt Version 26

I have (finally) pushed a new version of Mymail-crypt for Gmail to the Chrome store (and github).

The extension visually appears and functions very similar to what you’re used, however, it’s got a hugely updated encryption engine underneath.

We’ve been refactoring and improving the Openpgp.js project significantly over the past year. In this version of Mymail-Crypt, I’m incorporating these changes for a better experience.

  • Support for more OpenPGP clients keys — great news if you’ve had trouble with other peoples keys in the past.
  • Better signature verification. There is now a “Verify Signature” button for messages that are signed but not encrypted. If a message is both encrypted and signed, Mymail-Crypt will attempt to verify the signature when you use the “Decrypt” button.

Really, there are a ton of improvements in the encryption library, but most of them are transparent. Now that this has been shipped, there are a number of other visual items and cleanup I’m hoping to turn my attention to.

Let me know if you have trouble migrating, or using the new extension!

Gmail is a-changing

It looks like Gmail might be in the process of changing the DOM layout for the site somewhat extensively. It appears that it is re-architecting some of it’s top level elements that will almost certainly break my extension among many others.

As I find out more and am able to address what the issue is, I will post what I find.

Hacking Gmail for Privacy and Profit

My goals for Mymail-Crypt for Gmail have always been to allow everyone to be able to use Gmail to simply, and privately send messages. I’ve recently had time to conquer one of the bigger challenges that I’ve only poked at before: stopping automatic draft saving.

However, the whole process was an exercise in backtracking, frustration, and bursts of satisfaction. This post is going to be very technical, and I write it in hopes that someone attempting to do something similar with Gmail or general extension hacking can find something useful. Feel free to reach out to me with any questions.

No, this is not how to read your ex-girlfriend’s email, and no, I don’t actually profit from this extension.

AJAX Attack!

Ok. Let’s make Gmail stop unloading drafts. These are sent via XHR (ajax), so let’s intercept that from our extension and stop them from uploading: = function(){

Nothing. That’s weird. I see in the debugger, XHR calls going back and forth, but my debugger call isn’t registering.

Ok I wonder if this is a limitation of Content Script Chrome extensions. I’ve looked at the Content Script Documentation before but, let’s try some experiments:

$('body').append('<script type="text/javascript">

Ok, I get an ever so pleasant alert popup on page load. JS DOM injection Works.

$('body').append('<script type="text/javascript">
window.XMLHttpRequest.prototype.send = function(){debugger;}

Doesn’t work. “Isolated Worlds” are in play. This is the limit of the content script sandbox. Time to take another approach.

Replace the composition box

So, if I can’t intercept the actual XHR messages, I think I’m going to have to change something on the page in order to prevent drafts from being visible. My first thought is to look at the composition form textbox. A quick look in the debugger shows that the code looks like this for the textbox:

<body g_editable="true" hidefocus="true" contenteditable="" class="editable LW-avf" id=":2ak" style="min-width:0;"><br></body>

I try replacing the :2ak with my own personal id. However, even after I make this change, the draft still gets uploaded. I try changing a few parent id values. Same response.

Higher in the DOM I find the form that is being submitted. When I rename this id value I get an error. Yay. My Fuzzing broke the page. I use the debugger to pause on all XHR requests. I confirm that the XHR request contents are essentially blank, as I would expect. This is a good sign.

Now, how do I make the page usable again.

Click hijacking

The first thing I try is to write a new on things that I think I could click on, notably a elements. However, Gmail doesn’t use a lot of a elements. I seemed to sometimes get into some sort of race condition depending on how I was binding .click() events. There seem to be two things at play here:

  1. jQuery by default will make a queue with event handlers, but this can be overridden
  2. (again) Content Script Chrome extensions have limitations on manipulating the host page javascript

Time to pivot, no, not pivot I’m not a startup change my strategy yet again.


Let’s try copying our form, I can leave the cloned form blank so Gmail thinks there is an empty message.


Initially, this is looking pretty good. I can change the id values and hide the form I don’t want Gmail to see. However, it quickly becomes apparent there is a serious issue with this approach. The text box is not editable. That’s weird. Uggh, part of the form is an iframe. After wasting an embarrassing amount of time trying to force the iframe html value to be what I want, it becomes apparent my approach isn’t working and the content isn’t loaded when I try to clone it. Duh, what if we just wait until it is loaded.

  var form = $('#canvas_frame').contents().find('[class="fN"] &gt; form').first();
}, 500);

Alright, this is looking good. I can edit the text as I would expect. Uggh, new problem, I’m stuck in some sort of weird state where either the drafts are continuing to save or I’m hitting my new favorite Gmail 707 error. I proceed to fiddle with this, changing exactly how I insert or what I do, for quite some time. It continues to not work. Awesome.

Take a break (always undervalued).


In fiddling with the cloning, I’m somehow slowly drawn back to my previous strategy of just renaming the composition form. Ok, so the major issue with this is that whenever I click any link I get a 707 error unless the form has the proper id. Let’s take a step back and see if somehow we can take advantage of the hierarchical structure of the DOM. What if I bind a mousedown on the main “canvas_frame” iframe object?

  alert('I'm CLICKING');

Boom. This works exactly as I want it to. Anywhere I click, I’m getting the alert. Now let’s try to refine this sledge-hammer approach to make it useful. I target the left hand side of the Gmail window:

Rather than a 707 error, I’m going to go ahead and assume you want to navigate away. If you don’t want drafts to autosave, navigating away means these should not be saved. So let’s rebind this left hand side

$('#canvas_frame').contents().find('[class="nH oy8Mbf nn aeN"]').mousedown(clearAndSave);
function clearAndSave(){
function saveDraft(){
    var form = $('#canvas_frame').contents().find('#gCryptForm');
    form.attr('id', formId);
    $('#canvas_frame').contents().find('div[class="dW E"] &gt; :first-child &gt; :nth-child(2)').click();

This works well. I similarly blank out other navigation links. To save drafts, I bind the appropriate button to call the saveDraft function. To send a message I again save a draft and fake click the send button. jQuery provides the powerful ability to generically select the Send button:

$('#canvas_frame').contents().find('div[class="dW E"] > :contains("Send")');

General Approach

You may have notice that I search Gmail page based on class. In my experience (too many hours), these are less likely to change between iterations. I try to make my jQuery selections as generic as possible but still get the exact element I want — it’s often hard to find the appropriate balance.

There’s some other craftiness in my solution, but this article is already far longer than I had anticipated, and shows the points I consider most important.


It works! The Gmail interface is not intended to be manipulated by people. Figuring out how the complex functionality of the application is difficult and takes a lot of guess and check.

I’ve added an experimental option to disable draft autosaving in the latest version of Mymail-Crypt for Gmail (source), (Chrome Web Store extension) using the approach described here.

gmail-crypt is now “Mymail-Crypt for Gmail™”, download now!

Download: Mymail-Crypt for Gmail™ Chrome Web Store Link

Name Change

There have been a lot of changes to gmail-crypt. Perhaps one glaring difference as the title notes is I have changed the name to “Mymail-Crypt for Gmail™” as part of my push to get the extension available in the Google Chrome Web Store. They seem to be quite concerned about how you use their trademarks, and I believe I have changed it to meet their standards.

Notable Technical Changes

  • The Options page has been revamped to use Bootstrap. There have been a number of changes to how the options appears. I hope it makes it more intuitive.
  • I’ve integrated the most up-to-date version of OpenPGP.js. In this version I have just recently finished some significant pushes to key generation. This means that you can now generate keys with passphrases.
  • I’ve added the ability to Encrypt with/without a signature, and to just sign a message.
  • Lots of bugfixes, general improvement

Security Concerns

I think this software is quite useful but there still are some special concerns in regard to using this software. You should weigh how important these concerns are to you:

  • DO NOT use this on a shared computer. This extension is not (yet) multi-user capable.
  • This release still allows drafts to be uploaded to Gmail servers. Unencrypted drafts could be stored on Gmail servers.
  • Storing private keys in browser. The extension will run under it’s own domain but it might be possible for malicious entities to access it.
  • Password input into the DOM. Currently input for passwords is done directly into the DOM. This means it would be conceivable for gmail to acquire this password. It is important to note that private keys are stored in the context of the extension and not gmail’s context.
  • Cryptographically Secure Pseudo Random Number Generator. OpenPGP.js uses window.crypto.* for random number generation, the quality of this is browser dependent. By definition this should be a good source, but is an externality to consider.

Make sure that you keep backup copies of all the keys you generate. If they’re lost, they’re lost.

TL;DR — There have been a ton of changes that make this extension much more polished. Give it a whirl. Read the Help page for some possible security concerns if that’s your style.

Download: Mymail-Crypt for Gmail™ Chrome Web Store Link
As always, the project page is available here