How can I use encryption with Gmail?

I'm currently reading Cory Doctorow's novel Little Brother which includes a part about encrypted messaging, and even wrapping messages first in my private key and then your public key.

I'd like to play around with that but from what I've googled so far it seems to be a rather convoluted process, requiring installing several program components, and creating an encrypted message requires doing some manual file manipulation.

I'm surprised that I can't find something like a Firefox plugin that integrates encryption into Gmail. I've seen that there is a Thunderbird PGP plugin, but I don't use T-bird. I also saw a blog post that Google apparently toyed with PGP support in 2009, but nothing has appeared in the meantime.

Question:
To use encryption with Gmail, is there a simpler method than creating a file locally, then encrypting that file, and finally attaching it to a regular Gmail message?

Solution 1:

Generally there are two approaches to achieve your goal. For this example I would tie with GPG as far as its open alternative to proprietary PGP, which I do not have license to use it. Basically you will need OpenPGP library as well as your public/private key pair.

Using Gmail in web browser

These are seamlessly integrated into browser, so in your Gmail session will be shown additional buttons on encrypted message - show original, decrypt and encrypt for new messages.

• Chrome: gmail-Crypt plugin
  • EDIT: If you cannot install above plugin, there's perfect alternative Mymail-Crypt for Gmail™
• Chrome/Firefox: mailvelope

Using own Thick Email Client

These are integrated into particular clients so you can import your keys as well as keys of your friends or add them on the fly. You can encrypt/decrypt message via context button.

• Outlook: gpg4win plugin
• Thunderbird: enigmail plugin

Generating key pairs

I prefer to use gpg4win which is delightful for this task using its front-end Kleopatra.

Final adjustments

I would advice to turn on forced SSL encrypted while visiting Gmail which can be configured in Settings -> General.

Solution 2:

Mailvelope is a new browser plugin that provides OpenPGP encryption for Gmail/Google Apps, Outlook, Yahoo!, and GMX. According to Lifehacker:

Mailvelope is in beta, and there's a full extension available for Chrome, and an early beta available for Firefox, but when we tested it both extensions worked well. Gmail/Google Apps, Outlook, Yahoo!, and GMX are all supported, and the app can be configured to support others. After installing the extension, you can generate your own public and private keys to use to encrypt messages in the extension's preferences. Once your keys are ready, the next time you compose a message, you'll see a lock in the compose window that you can click to encrypt your message. You can even use multiple keys for multiple recipients.

When you get an encrypted message, the process works in reverse. You'll see the encrypted message with a lock overlay over it, and you can click it to enter your key password. Mailvelope will search your saved keys to find the one needed, and decrypt the message for you.

Solution 3:

Well I do not see the problem about using an email client. Keep in mind you will always need to install a private key - so why not a client.

Personally I actually use S/MIME instead of gpg as this is wider supported (even supported on iOS devices - and I think also Blackberries) - and gives similar security. Btw there is even a firefox plugin.

If you need gpg some editors (emacs, vim and probably many more) allow you to encrypt text. You could copy and paste that - or use a plugin.

Solution 4:

Yes, there is. A similar question has been asked here. There are/were several add-ons or plugins for Firefox and Chrome. I've always wanted to try some of them, but I've never had the time.

• There was FireGPG for Firefox, but it is dicontinued. I don't know if there is a follow-up project on this.

• For Chrome, there is cr-gpg, you could give that a try