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Let’s talk email encryption

I used to nudge people toward encrypting their emails. “Encrypt everything!” I’d burble. “Even your cookie recipes! It protects privacy and drives ‘them’ crazy!”

“Quick! Easy!” I continued to burble as I wrote “The Hardyville Beginner’s Guide to Encrypt**n” lo those many years ago (now obsolete, which is why no link).

I eventually quit burbling.

It’s not that I quit favoring encryption. I just got tired of hearing, “It’s too haaaaaaaaaaard.” I got tired of, “Well, if you want me to encrypt my emails to you, you’ll have to show me how.”

Since I might have been the only person they knew who wanted encrypted correspondence, the latter wasn’t entirely unreasonable. Just incredibly time-consuming and very difficult, since everyone’s system was different.

I still encrypt email with old friends. But I gave up the evangelizing (though encryption does get a passing mention in Rats!, the anti-snitch book). It’s been so long since I added a new encryption partner that this week when Michael W. Dean raised the subject and sent me his key, I’d almost forgotten how to add it to my keyring.

But. Let’s try this again. Michael (yeah, we’re seeing a lot of him this week) commissioned a couple of guys to write an email encryption tutorial and a couple other guys to reality check it.

Here it is. On Freedom Feens. It’s good.

Yes, it has a lot of steps. They aren’t hard steps. If you use the Thunderbird mail client, you’ve already done most of them.

The tutorial cuts through a lot of encryption confusion by just assuming that you will set up and use Thunderbird and its Enigmail plugin. It assumes well. Once you’ve set up encryption, Thunderbird and Enigmail make using encryption virtually effortless. (So effortless, in fact, that it’s easy to forget whether you’ve encrypted an email or not. Yeah, ask me about that one. But there are settings to help with that.)

It also instructs you to use the encryption software GPG4Win (GNU Privacy Guard for Windows). “It’s free! It’s EZ!” I burble.

If you don’t use Windows, you can get other GPG versions here. It’s free. It’s not quite so EZ. But non-Windowsians are used to that. (Use the manual, not one of the HOWTOs; HOWTOs are just strange documents computer geeks use to communicate with each other while totally baffling the rest of us. But the manual is actually useful.)

Back to the Freedom Feens tutorial. It’s good. “Easy!” I burble again.

And most of the setup is the same, no matter what operating system you’re on.

It’s always been hard to get started because it takes two to encrypt. Maybe your 90-year-old maiden aunt will never do it. But for heaven’s sake, if you genuinely want to protect your privacy (and not just yammer about its loss), you should. And so should the people you regularly correspond with — even if you’re discussing things you consider innocuous.

If you don’t already have friends who encrypt, maybe we can get some volunteers to serve as encryption guinea pigs. Then once you know you’re set up for secure email, maybe you can be coach and guinea pig for your friends.

But for heaven’s sake, if you say you want “them” — the snoops, public or private — out of your life, take this one, simple, long-lasting step to kick their snoopy asses to the curb — encrypt!


  1. David
    David December 13, 2012 6:06 am

    I really, really wish that–back when I used to try this–I had convinced one person to send encrypted email. Just once.

    I’m not good at convincing people of anything, and in this case I just totally sucked.

    But okay! Claire, next time I write I’ll send a public key. It’ll be good for my soul.

  2. ILTim
    ILTim December 13, 2012 6:34 am

    I balked at all things encryption forever. Finally I took the plunge and learned about truecrypt, and now I’d feel naked without it. An encrypted trucrypt container is like a jump drive, but instead of plugging it in to a usb port, you unlock the file with a program. Easy peasy.

    Email encryption is still ‘out there’ to me, but I suppose that’s because I really don’t use it much except for work. I also use iThings and webmail and havent touched a desktop email client in…. what?… almost ten years? Now I know that you can copy/paste blobs of encrypted goo into another program for translation, even on an iphone, but that’s a hard sell for cookie recipes.

  3. MamaLiberty
    MamaLiberty December 13, 2012 9:18 am

    I’ve been using PGP – and more recently GnuPG for a long time – usually only with a half dozen or so. And yes, it’s gotten much, much easier. 🙂

    I’ll send my public key if anyone wants to write to me. Include your key with the first message. mamaliberty at rtconnect dot net Replace at and dot with the approriate symbols and no spaces.

    Anybody want my recipe for “dog noodles?” My dog loves them. LOL

  4. Claire
    Claire December 13, 2012 9:24 am

    MamaLiberty — That’s great! I hope people take you up on your offer.

    While I’m not going to invite new correspondence (sorry; already overwhelmed), if anybody who already has my email address wants to set up encryption and send me his or her public key, I’ll send mine, too, so people can test their new setups.

    In my keyring, I also see people with whom I used to encrypt but don’t any more. If any of those people have let their encryption go (due to changing systems or whatever) and want to re-establish it, send me a new key.

  5. Claire
    Claire December 13, 2012 9:27 am

    David — and good for things besides your soul, too. 🙂

    ILTim — Hm. Encryption on mobile devices. That I know nothing about. Maybe Dean and company will do something on that. I know there’s already a lot of native encryption, but (as with any encryption done in and by “the cloud,” I wouldn’t trust it). And how can there really be any privacy with a device that broadcasts your identity and position to Authoritah?

  6. Woody
    Woody December 13, 2012 11:50 am

    I use encryption extensively for documents and whole drive encryption. I only ever convinced 2 correspondents to use encrypted email. Eventually they both got tired of it, so that was that. I also haven’t used a desktop email client in years. I’m very happy with my proxy services web mail. I used PGP until that went away except for enterprise users. When I switched to Win7 I had to switch to GnuPG4Win from free PGP 6.x.x. Unfortunately the interface is very clunky compared to the old versions of PGP.

    Frankly, except for “geek points” I see very few practical reasons for me to use encrypted email, especially lacking willing correspondents.

  7. The Infamous Oregon Lawhobbit
    The Infamous Oregon Lawhobbit December 13, 2012 12:20 pm

    For a value of “nudged” that includes “yelled and hollered at me severely,” yeah. 🙁

    So are you sure your PGP doesn’t have a back door? I seem to recall a big messy noise about that at one time.

    On the other hand, there’s always steganography. I’ve got a couple of programs floating around for that, too, somewhere.

  8. Claire
    Claire December 13, 2012 12:27 pm

    Hobbit — It’s possible that PGP proper does have a backdoor these days. But GNU Privacy Guard (GPG), which both the Feens tutorial and I recommend, is open source. A backdoor would be spotted.

    But moi, yell at you??? Nevah!

  9. Claire
    Claire December 13, 2012 12:28 pm

    Woody, part of the idea is to drum up more willing correspondents. Or rather, not more correspondents, but more willingness.

    It’s definitely been a problem, though.

  10. jed
    jed December 13, 2012 5:11 pm

    I first messed with encryption (other than decoder rings in Cracker Jack boxes) in, I think it was, 1986. And then not for a while, until the lights came on sometime in the late 90’s. Pretty fascinating stuff, if you read about the history and practice over the years. I have tried, a few times here and there, to get correspondents interested in it, but have never made any useful headway. And these days, I send very little e-mail anyway, and most of that is to my mother who I just can’t see using encryption.

    In March 2005, I gave a couple presentations on how to use Gnu Privacy Guard (GPG) with Sylpheed (which, btw, is a really great e-mail client). The steps are still going to be much the same — generate a key pair, self-sign it, tell your e-mail client where to find your keyring, and send out your public key. You can upload your public key to one or more of a number of keyservers too.

    I will comment that in a world of surveillance, I wonder about the degree to which an occasional encrypted message will be a flag. There’s more to snooping than intercepting messages; there’s traffic analysis too. That’s why I would like nothing better than for all network traffic to be encrypted — nothing stands out that way. Real world, that isn’t going to happen.

    I will also comment on the practice of signing someone else’s key. Don’t do it, unless you’re completely sure of what you’re doing. I actually don’t like the trust model of PGP (and GPG — same thing), not because it’s necessarily a bad model, but because I doubt that many people go through the effort to understand what it means. Just remember, that if you exchange keys via e-mail, the most you can say about that key is “it’s the key for the person using this e-mail address”, and that you can’t really impute more meaning to it without taking further steps. What I mean by that is that, e.g., if Claire sends me her public key, I know only that it’s the key for a person using that e-mail address, but in point of fact, I don’t know with certainty that it’s really Claire. For casual purposes, this isn’t particularly meaningful, and I have no reason to doubt that it’s really Claire. (There could be a long digression here on the whole problem of bootstrapping identity.) I don’t mean to argue against using encryption, just be sure you understand what the key does, and doesn’t represent.

    If you want to get into signing other people’s keys, then go to the GnuPG HOWTO page, and scroll down about halfway to GnuPG Keysigning Party HOWTO (yes Claire, it’s a useful HOWTO 😉 ). The key signing instructions apply no matter whether you’re using GnuPG, PGP, or something else.

    Mr. Hobbitsseesssss, I am unaware of any backdoors with PGP. There was the whole Clipper chip debacle a while back, and some interesting things with NSA and DES. I wouldn’t be surprised at weaknesses or backdoors in some programs which implement public-key cryptography, but do it poorly. As Schneier says, good cryptography is hard. But at least at the user level, it is getting easier.

    Also, check out Silent Circle — no, not the German Eurodisco band. Silent Circle.

  11. jed
    jed December 13, 2012 5:13 pm

    Oh, and when you generate your key, always generate a revocation certificate.

  12. jed
    jed December 13, 2012 5:43 pm

    It also occurs to me to me that, irrespective of anything else, one good to reason to start using encryption now is to learn those skills, for the time when you actually need it.

  13. TOR
    TOR December 13, 2012 9:02 pm

    I think the utility of this type of encryption depends a lot on who you are trying to keep something from. Barney Fife can’t beat this stuff but anybody more serious can. Sorry but some guys putting together a free program do not beat groups of PHD holding geniuses with all the time in the world and super computers. Thinking anything else is fantasy. Then again if you are seriously worried about PHD holding geniuses with super computers I would go old school and talk to people face to face. It has worked for the Mafia and Al Qaeda as well as anything could.

  14. jed
    jed December 13, 2012 10:25 pm

    Tor, it’s actually a question of time, complexity, and scale. To say that ‘anybody more serious can’ is not supportable, given appropriately strong passphrases and key lengths. It is, however, similar to an arms race, and what is a good key length now might not be 10 years from now. A major breakthrough in quantum computing will turn the encryption world on its head.

    But I note (not recalling the gory details) a recent high profile bust (FBI I think) in which the primary tool used was a keylogger. The LEOs didn’t need to crack the encryption being used, because they’d already captured the passwords. If decryption were so easy, then why the recent court cases over compelling a suspect to reveal her passphrase?

    ‘All the time in the world’ is a non-useful timeframe. A secret which needs to be kept for a year is fine if the compute time to brute-force the encryption is 2 years. And there are limits to how many GPUs and/or CPUs can be used in parallel to cut the crack time. Granted, strides are being made in this area, but last I checked, a 1024 bit public-key isn’t in danger of a brute-force attack.

    ‘Some guys’ is an unwarranted backhand slap at the people who are working on this stuff. Some of them are PHD holding geniuses too. They contribute their expertise, in effect, pro bono.

    With that out of the way, I will add that in re. signing keys, the ‘local only’ signature option either wasn’t there the last time I was messing with this stuff, or I hadn’t found it. This would be the only acceptable way to sign a key without doing due diligence to verify identity. (Now that would make an interesting discussion all by itself — what is ‘identity’, and how do you really establish it?)

  15. Hanza
    Hanza December 14, 2012 3:56 am

    Years ago I read an article about 3 guys in California that came up with an encryption method, and they filed a patent application on it.

    U.S. laws require that any patents of that type have to be veted by NSA. NSA did its thing, and the government refused to issue the patent, classified the program, and under penalty of law told the authors never to discuss their program again.

    Out of the kindness of their hearts the govt. paid the 3 guys $100,000 for their efforts.

    You can be assured that *if* a patent was issued that the NSA can break the system.

  16. Claire
    Claire December 14, 2012 6:53 am

    TOR — What jed said. Besides, as much as anything else, using encryption is about privacy — and about declaring our right to it — rather than actual secret keeping.

    I don’t doubt that if “they” want to get you and “they” believe you possess some important secret, they’ll dedicate a lot of computing time and brainpower to breaking your encryption. But if millions of people encrypt email as a matter of routine, without any big secrets, that’s a different situation altogether.

    Everyday encryption can do such everyday things as keep advertisers from analysing our correspondence. If the feddies are scanning mail for keywords — most of which are pretty innocuous, everyday words — everyday encryption stymies them.

    Granted, the very act of encrypting is something the Homeland (Achtung!) Security people consider “suspicious.” But that’s why you encrypt as much as you can to as many people as you can; to make it routine.

  17. S
    S December 14, 2012 10:56 am

    For those that have the $ to trade for their time, the $99 version of PGP is waaay easier to set up and use. I use both PGP and GPG/Thunderbird/Enigmail, and Thunderbird in particular has been a PITA more than once.

    Give the PGP site a credit card number, download a file, point and click a few times, and you’re ready to set up key rings, make keys, encrypt files, and pretty much everything else.

    Maybe PGP has a back door. Maybe not. PGP and GPG are both single mile-high pickets in the picket fence you must erect to ensure your privacy. The primary vulnerability isn’t back doors. XKCD gets it:

    Let’s face it; if you become a person of interest, they will get your files, one way or another. Encryption won’t stop lawless thugs who use torture and worse. It may slow them down, at least for a while.

    Backdoor or not, encryption is an excellent first step into taking responsibility for your email and computer file privacy.

  18. MamaLiberty
    MamaLiberty December 14, 2012 11:51 am

    I’d suggest anyone at least try the GnuPG first, before they spend the bucks on the paid thing. I’ve used a dozen or more forms of this encryption through the years and have seldom had any real problems, especially since converting everything to linux. I can’t speak for current windows users, of course, but i didn’t have problems back then either, in spite of the fact that the encryption program itself was not nearly so user friendly then.

    But do try it, either way. 🙂

    Write to me. I’ll give you my recipe for potato bread too!

  19. Charles Pergiel
    Charles Pergiel December 14, 2012 2:23 pm

    I am of two minds on this encryption business. On one hand I’m all in favor of it, it’s nobodies business what I write. On the other I’m thinking it’s like waving a red flag at a bull. Hey! Lookie here! I’ve encrypted my email! I bet you can’t de-crypt it! Neener neener neener! Given proper motivation I am sure there is nothing the NSA can’t crack. I prefer slight of hand methods. Put on a big show of normalcy, and while everyone is busy watching the show, go out the back door and go ahead with what you really want to do.

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