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net.wars: Crypto: the revenge

by Wendy M Grossman | posted on 28 October 2011


I recently had occasion to try out Gnu Privacy Guard, the Free Software Foundation's version of PGP, Phil Zimmermann's legendary Pretty Good Privacy software. It was the first time I'd encrypted an email message since about 1995, and I was both pleasantly surprised and dismayed.

Wendy M Grossman

First, the good. Public key cryptography is now implemented exactly the way it should have been all along: once you've installed it and generated a keypair, encrypting a message is ticking a box or picking a menu item inside your email software. Even key management is handled by a comprehensible, well-designed graphical interface. Several generations of hard work have created this and also ensured that the various versions of PGP, OpenPGP, and GPG are interoperable, so you don't have to worry about who's using what. Installation was straightforward and the documentation is good.

Now, the bad. That's where the usability stops. There are so many details you can get wrong to mess the whole thing up that if this stuff were a form of contraception desperate parents would be giving babies away on street corners.

Item: the subject line doesn't get encrypted. There is nothing you can do about this except put a lot of thought into devising a subject line that will compel people to read the message but that simultaneously does not reveal anything of value to anyone monitoring your email. That's a neat trick.

Item: watch out for attachments, which are easily accidentally sent in the clear; you need to encrypt them separately before bundling them into the message.

Item: while there is a nifty GPG plug-in for Thunderbird – Enigmail – Outlook, being commercial software, is less easily supported. GPG's GpgOL module works only with 2003 (SP2 and above) and 2007, and not on 64-bit Windows. The problem is that it's hard enough to get people to change *one* habit, let alone several.

Item: lacking appropriate browser plug-ins, you also have to tell them to stop using Webmail if the service they're used to won't support IMAP or POP3, because they won't be able to send encrypted mail or read what others send them over the Web.

Let's say you're running a field station in a hostile area. You can likely get users to persevere despite these points by telling them that this is their work system, for use in the field. Most people will put up with a some inconvenience if they're being paid to do so and/or it's temporary and/or you scare them sufficiently. But that strategy violates one of the basic principles of crypto-culture, which is that everyone should be encrypting everything so that sensitive traffic doesn't stand out. They are of course completely right, just as they were in 1993, when the big political battles over crypto were being fought.

Item: when you connect to a public keyserver to check or download someone's key, that connection is in the clear, so anyone surveilling you can see who you intend to communicate with.

Item: you're still at risk with regard to traffic data. This is what RIPA and data retention are all about. What's more significant? Being able to read a message that says, "Can you buy milk?" or the information that the sender and receiver of that message correspond 20 times a day? Traffic data reveals the pattern of personal relationships; that's why law enforcement agencies want it. PGP/GPG won't hide that for you; instead, you'll need to set up a proxy or use Tor to mix up your traffic and also protect your Web browsing, instant messaging, and other online activities. As Tor's own people admit, it slows performance, although they're working on it (PDF).

All this says we're still a long way from a system that the mass market will use. And that's a damn shame, because we genuinely need secure communications. Like a lot of people in the mid-1990s, I'd have thought that by now encrypted communications would be the norm. And yet not only is SSL, which protects personal details in transit to ecommerce and financial services sites, the only really mass-market use, but it's in trouble. Partly, this is because of the technical issues raised in the linked article – too many certification authorities, too many points of failure – but it's also partly because hardly anyone understands how to check that a certificate is valid or knows what to do when warnings pop up that it's expired or issued for a different name. The underlying problem is that many of the people who like crypto see it as both a cool technology and a cause. For most of us, it's just more fussy software. The big advance since the mid 1990s is that at least now the *developers* will use it.

Maybe mobile phones will be the thing that makes crypto work the way it should. See, for example, Dave Birch's current thinking on the future of identity. We've been arguing about how to build an identity infrastructure for 20 years now. Crypto is clearly the mechanism. But we still haven't solved the how.


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Wendy M. Grossman’s Web site has an extensive archive of her books, articles, and music, and an archive of all the earlier columns in this series. Readers are welcome to post here, at net.wars home, follow on Twitter or send email to netwars(at) skeptic.demon.co.uk (but please turn off HTML).