Fairly Secure, Actually

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Many of us had assumed our feeble Gmail passwords were secure enough to keep prying eyes out of our email accounts. But with revelations that the NSA can pretty much demand any email service turn over valuable and private information about our email, more attention has been turning to sources for encrypted secure email services.

So what can you use for secure email now?

 Email is basically not secure. There are steps you can take to protect yourself, through both free and paid services, but the U.S. government has shown its willingness to compel even legendary secure email services like Lavabit–which Edward Snowden used for five years–to shut down. If you’re truly paranoid, here are your options.

Instant Messaging

Instant messaging, often referred to in security circles as “synchronous communication,” is, surprisingly, often more secure than email. The way to go here is with a setup called OTR, or Off The Record Messaging. OTR was set up to provide deniability for metadata, which means that unlike with many less-secure kinds of email, even if somehow you get your hands on a transcript, there’s no way to prove exactly who was communicating. Each individual message is highly encrypted using AES keys, which means that any hacker would have to decrypt each message to get the entire conversation–and decrypting one AES key is a task worthy of a team of hackers. OTR is also fairly easy to use; you can get a plugin for popular chat clients like Adium, Pidgin, and IM+ (the latter costs extra).

Back to Email

But, okay, say you need asynchronous communication, meaning you have to send a message and have the receiver open it at some later point. There are ways to make email really difficult to crack, though the fact that the U.S. has the legal authority to demand metadata throws a real wrench into the whole setup. Still! There are still some for-pay email providers (largely based outside the U.S., now) that use powerful security like OpenPGP and public-key encryption, and which swear they won’t let the man snoop in your data.

Public-key encryption is an underlying idea beneath most secure digital messaging. Each user has two keys: a public key and a private key. These are mathematically related, though it is essentially impossible to figure out the private key from only the public key. Imagine that you have a box. Only you have the key to open it. But you can send this box, unlocked, to anyone, so it’s public, and they can put whatever they want in the box. Then that person locks the box, so now even they can’t get it open. They send the locked box back to you, and you open it with your private key. If you want to respond, you’ve got to do the same with their unlocked box. The major benefit is that you never have to share your key with anyone else.

OpenPGP is software that uses public-key encryption; it’s free to use (hence the “open” part) and is available on a wide variety of platforms. It handles the creation and authentication of keys, among other things. PGP stands for “Pretty Good Privacy,” which isn’t that encouraging, but it’s the most widely used cryptographic standard in the world.

GnuPG: GnuPG is a very popular free implementation of OpenPGP. You can use GPG with one of a variety of front-ends as a plugin for encrypting your emails through your choice of email programs, from Apple Mail to Outlook to Gmail. But they require some setup, and there are paid services that will handle it all for you and which offer advanced features like hidden IP addresses, destruction of files after a period, and offsite storage in friendlier countries. And this is a very popular option for those who can figure out how to use them; it’s the most popular recommendation on this Slashdot thread, for example.

But! Assuming you’re not ready to set up your own email encryption, you want to look for email services that use OpenPGP. Here are some options:

Countermail: Countermail is a paid service which keeps its servers in Sweden. It uses OpenPGP, but also has some advanced options like a hardware USB key, so nobody can even start the email process without inserting a USB drive into the computer. Countermail also does not use any hard drives during the sending of emails–they actually use CDs–so there’s no chance of your IP address being logged anywhere. It’s not cheap, though; you can buy it in packages, the cheapest of which is 24 months for $100.

Bitmessage: Bitmessage is a newish service, created in the style of Bitcoin. It also uses public-key encryption, but when you send an email, it mixes it with all other emails being sent, which makes it pretty much impossible for anyone in the middle to figure out from where the email was sent. They also don’t have any information as to the receiver of the email, so each individual message contains the data from every other message that’s also going through Bitmessage. The receiver’s key, however, only retrieves the message that was intended for his or her inbox. Messages are also not archived; to keep from having a bazillion old emails floating around, being downloaded all the time, messages are deleted after two days. It’s completely decentralized, which might make it the best option for those who fear the government. Who is the government going to issue a request to? There’s nobody in charge!

NeoMailbox: Based in Switzerland, NeoMailbox is a traditional paid service like Countermail. It uses OpenPGP encryption, but also has some nice features, like the option to choose your own domain or use an unlimited amount of disposable email addresses. It also might be the easiest to use; it plugs into lots of existing mail services like Thunderbird, Outlook, and even has an Android app. Depending on how much storage you need, NeoMailbox ranges from $50 a year (1GB) to $110 a year (10GB).

Hushmail: Hushmail is perhaps the best-known alternative to Lavabit and Secret Circle. It’s also available for free, at least for some basic features, which is pretty nice. For free, you get OpenPGP encryption, 25MB of storage, any domain you want, and a nice web-based service. For a little extra you can more storage and your IP address hidden. But Hushmail has been controversial; it’s based in Vancouver, and has previously handed over records when requested by the British Columbia government. Hushmail says it won’t respond to foreign demands, but I’d recommend one of the other services instead, just in case.

Another interesting possibility is Pond, an asynchronous communication service that has its messages expire a week after they’re opened, with no exceptions. It isn’t ready yet, though; its creator says “Dear God, please don’t use Pond for anything real yet.” But it’s promising.