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Moxie Marlinspike: GPG Has Run Its Course

An anonymous reader writes: Security researcher Moxie Marlinspike has an interesting post about the state of GPG-encrypted communications. After using GPG for much of its lifetime, he says he now dreads getting a GPG-encrypted email in his inbox. "Instead of developing opinionated software with a simple interface, GPG was written to be as powerful and flexible as possible. It's up to the user whether the underlying cipher is SERPENT or IDEA or TwoFish. The GnuPG man page is over sixteen thousand words long; for comparison, the novel Fahrenheit 451 is only 40k words. Worse, it turns out that nobody else found all this stuff to be fascinating. Even though GPG has been around for almost 20 years, there are only ~50,000 keys in the "strong set," and less than 4 million keys have ever been published to the SKS keyserver pool ever. By today's standards, that's a shockingly small user base for a month of activity, much less 20 years." Marlinspike concludes, "I think of GPG as a glorious experiment that has run its course. ... GPG isn't the thing that's going to take us to ubiquitous end to end encryption, and if it were, it'd be kind of a shame to finally get there with 1990's cryptography."

20 of 309 comments (clear)

  1. Same error, repeated by Anonymous Coward · · Score: 5, Interesting

    I suspect some of the cruft is due to its PGP heritage, but really, all the options aren't the problem. The length of the manpage, neither. Here you have a decently documented piece of software and you complain about the volume? Psah. No, that really isn't the issue. Nor is the ability to have multiple algorithms, as the state of the art keeps on advancing and so you need to replace algorithms now and then.*

    The issue is that the interface, the way it packs up crypto for ease of use, is something only a crypto-nerd could love. The basic principles aren't hard to explain to an intelligent lay(wo)man, but understanding how the web of trust works, nevermind make intelligent decisions that make sense, that even crypto-using nerds usually don't manage. And that's just the model; the implementation is clunky to the point that even programs employ intermediate libraries that then barely work for this or that ill-conceived reason.** And then there's the interface as ment for humans. Again, it's nerd-only.

    That nerd-only-ness is an obstacle to uptake, and that again is a problem. We desperately need crypto in email, but what bank even publishes GPG and S/MIME keys for securing email? I know of one, and it's a central bank so mere mortals cannot open accounts.

    So for a long time GPG has only been supported by a single person, props to him, who evidently doesn't know much about usable user interfaces, not even CLI ones. Yet I'm not blaming just him for it, either. Look at openssl: Again a bit of crypto software that turns out to be pretty damn important, and there's only a few boobs holding down the fort. That is actually poorer documented and even clunkier to use. The code, starting from the APIs, isn't so hot either. No wonder it came crashing down spectacularly. But that too is a problem.

    So we have a couple real problems, yet this security expert managed to pin only non-problems. And that itself is again a problem.

    * One thing that is a problem is the headers inserted on top of the message that really ought to've been encoded in the signature, since they belong there and moreover there's no real need to put them anywhere else. In fact, the current practice causes transport problems making the format more brittle than it needs to be.
    ** Work out why gpgme doesn't work so well on 64-bit windows, especially where the individual programs may or may not actually be fully 64bit. It literally doesn't work because some maintainer disabled the workaround that made it work because that somehow "does not make sense" to him.

    1. Re:Same error, repeated by AmiMoJo · · Score: 5, Interesting

      I know quite a few people who have started using GPG via the Enigmail plug-in for Thunderbird lately. The length of the man page is irrelevant and they never publish their keys so are effectively invisible to the statistics. That doesn't mean that it isn't an extremely useful, valuable piece of software though.

      Now more than ever we need GPG, and I bet adoption has gone up a lot in the last year.

      --
      const int one = 65536; (Silvermoon, Texture.cs)
      SJW, n: "Someone I don't like, and by the way I'm a fuckwit" - AC
    2. Re:Same error, repeated by rvw · · Score: 4, Informative

      I know quite a few people who have started using GPG via the Enigmail plug-in for Thunderbird lately. The length of the man page is irrelevant and they never publish their keys so are effectively invisible to the statistics. That doesn't mean that it isn't an extremely useful, valuable piece of software though.

      I use Thunderbird with Enigmail, mostly to sign my emails to get other people used to seeing signed mails, with an attachment with the signature in it. I've got one question about this, a friend asking what that mysterious attachment was and I explained it. I created an IMAP mail account that I only use to make notes that I can easily share among different computers. All these notes are encrypted using my public key. I can open them on the computer which has my private key.

      Your comment about being invisible to statistics does not mean being invisible to NSA and GCHQ. As they and several other agencies scan all mail, they will see these attachments, they will see mail headers and other signs that mail being encrypted, whatever method you use. So they will know that your friends use GPG.

    3. Re:Same error, repeated by pthisis · · Score: 4, Informative

      Why use gpg instead of s/mime, which has native support in most e-mail programs, with no need for plugins? S/MIME relies on centralized key servers or opens itself to man-in-the-middle attacks. You can hand-authenticate individual CAs with some effort, but there's no equivalent to PGP's web of trust. And CAs are single points of failure, making them extremely desirable points of attack. Marlinspike, of course, has developed his own proposed solution to the CA problem: http://en.wikipedia.org/wiki/C... It's up to the reader whether this contributes to his credibility on the issue because he knows what he's talking about and has taken the time to contribute code to help fix the problem, or whether he's someone with his own personal dog in the fight and hence has an ulterior motive in denigrating PGP's trust model.

      --
      rage, rage against the dying of the light
  2. That's great, but... by wonkey_monkey · · Score: 5, Funny

    ...what do the other characters from Harry Potter think?

    --
    systemd is Roko's Basilisk.
  3. Another bad omen for privacy and security by qwijibo · · Score: 4, Insightful

    It's a bad sign when those who care about security lose interest. The NSA is doing their part to eradicate secure crypto. Law enforcement agencies are commonly breaking the law to fish for potential criminals. The only protection available is what's written by people who are not subject to influence from the NSA. That's increasingly meaning open source or non-US-based companies.

    Crypto is hard to get right. It's hard for the average person to know what ciphers or tools to use and which are just snake oil. It's hard to implement correctly so that it is secure. New ciphers are written by people who have a lot of experience in breaking the old ones. As the old guard ages out, I don't see the same depth of interest in the next generation. With crypto, there's no quick fix, and the new hotness doesn't come overnight.

    On the other hand, the 1990s cryptography he mentions would be a huge improvement over many things we have today. Since the 90s, I've wanted the ability to have cryptographically signed financial transactions. Instead of financial institutions and credit reporting agencies using shared secrets, I'd like to have the ability to authenticate with a public key. I'd like to provide my public key in person to my bank so they know I'm authorizing transactions. Instead, they rely on secrets which are available to anyone who's willing to spend a few bucks and maybe break a few laws. Identity theft is so prevalent because we're basically relying on writing (at least a 4000BC technology) for security instead of good crypto. Hell, bad crypto would be an improvement over most of what's being done today.

    I hope his opinion isn't representative of more people who have been involved with security and privacy issues, but unfortunately, I think it will resonate with a lot of us.

    1. Re:Another bad omen for privacy and security by Kjella · · Score: 4, Interesting

      Crypto is hard to get right. It's hard for the average person to know what ciphers or tools to use and which are just snake oil. It's hard to implement correctly so that it is secure. New ciphers are written by people who have a lot of experience in breaking the old ones. As the old guard ages out, I don't see the same depth of interest in the next generation. With crypto, there's no quick fix, and the new hotness doesn't come overnight.

      Crypto is easy. Ciphers are easy. Here's a key you can use it to sign and verify messages, open and seal envelopes.

      Using crypto is hard. People lose keys, forget passwords, don't transmit keys in a secure way, don't store keys in a secure way, revoking keys, checking for revocation, using third party services like webmail and so on. Strong crypto is like losing your house key and being told that sucks, but since it's an impenetrable bunker with an unpickable lock there's nothing you can do but start from scratch.

      People want recovery options. If my house burns down to the ground and I escape with no passport, no driver's license, no identification of any kind the government will get me a new one. Work will find a way to get me a new access badge and key fob. That's why all those ways to recover your account exist, they're not necessary per se and you don't have to answer the security questions seriously. But when you have fucked up big and the answer is just gibberish you're pretty screwed. That's why people answer those with actual facts.

      --
      Live today, because you never know what tomorrow brings
  4. git blame by Anonymous Coward · · Score: 5, Insightful

    Blame Google for not implementing it in Gmail -- Then they wouldn't be able to get ad revenue and user metrics from their "free" email service.

    Blame MS for not integrating it into Outlook, but why would we expect MS to actually want security in any of their products?

    Blame Mozilla for the creaky plugin and cumbersome import/export publish keys interface in Thunderbird, and support for SMIME over GPG by default.

    Blame the users mostly for not giving a fuck about encryption.

    Personally, I don't give a fuck. Most people don't care about encryption but the ones that do, do. Some take the time to setup GPG with an email client and it actually works quite well despite my complaints about the clunky interfaces.

    I can tell you this much: Fuck publishing ANY open source software without signed and verified GPG signatures. You better have a replacement for the "experiment" that's securing the world's biggest open source projects source code, buddy, or you can GTFO for being a sensationalist maroon.

    TL;DR: People who need GPG use GPG. Those that don't give a fuck don't give a fuck. Seriously, if the average person can figure out how to use the bullshit set-top box with horrible remote control interfaces, they COULD use GPG if they wanted to, but they don't.

    1. Re:git blame by Tom · · Score: 4, Insightful

      Blame the users mostly for not giving a fuck about encryption.

      That is stupid. It's like saying blame the drivers for not giving a fuck about fuel injection. Users should not have to care about encryption. They should care about having secure and private communication, and how to make that happen is our job, it's why we are being paid more than burger flippers.

      --
      Assorted stuff I do sometimes: Lemuria.org
  5. Re:get to work by Troed · · Score: 5, Informative

    Yeah. If only there was an easy to use end2end encrypted mobile phone application for voice calls that Moxie had been involved in creating.

    https://en.wikipedia.org/wiki/...

  6. Re:get to work by Anonymous Coward · · Score: 5, Informative

    The point is that Moxie actually *does* something (has the OP done anything? We don't know).

    I don't agree on everything with Moxie, but fact is that he's not sitting on his hands, by a long stretch.

  7. Back office by Minupla · · Score: 4, Insightful

    I partially agree with Moxie, GPG/PGP as an email encryption standard is never going to reach the "my mother uses it" point of say Skype. That doesn't mean its run its course. I also think it's disingenuous to imply that the number of keys on the public key servers is a useful proxy for utilization rates.

    In my company we use GPG every day. Most people who work there have no idea that we do. It's used in sensitive communications at high levels between organizations, e.g. to send documents to auditors. It's also used in a huge number of automated processes to encrypt data during the DB extract process so we can move that data out of the DB network and send it to partners.

    We don't send those keys to a public keyshare. That would provide attackers information and we don't do that (ya, security through obscurity sucks if it's your only line of protection. If you're using it to make life just a bit more difficult for an attacker tho, well I'm always for that!)

    Now all that having been said, I have great respect for Moxie, and maybe he has the Next Great Thing up his sleeve. I hope to see it at Defcon :).

    Min

    --
    On the whole, I find that I prefer Slashdot posts to twitter ones because I don't get limited to 140 chars before
  8. Moxie's security advice to me: by Burz · · Score: 4, Interesting

    I simply asked him -- in a private email -- if there was a signature for Convergence someplace because I didn't see any online.

    He accused me of being "inflammatory" and stated it was necessary to "take a leap of faith" (i.e. download and run it without verification). This was back in 2012, mind you. He appeared to be oddly anti-PGP back then, too.

    Frankly, after that I had no appetite for any more of his, erm, style and forgot about Convergence. Years later, I had to abandon DoNotTrackMe (by a Moxie-run company, Abine) nee 'Blur' for Ghostery instead when the former got an update that kept hogging the CPU. An email to Abine just yielded a response to keep updating Blur, but the problem never went away.

  9. Said this 14 years ago. We need to replace E-Mail. by Qbertino · · Score: 4, Insightful

    I was saying all this 14 years ago.
    FOSS Encryption is a mess. It is basically impossible for a regular user to set up encrypted mail.
    I'm an expert, and I never even managed too. (The K-Mail crew basically lying about their GPG-features didn't help back then)

    Furthermore, the actual, underlying problem is E-Mail.

    That this piece of crap protocol/service could survive for so long totally amazes me. I remember using Fidonet and Crosspoint, back in the 90ies (which actually is a superiour solution to E-Mail) and then learning about E-Mail and thinking "Why is everybody using this and thinking it's great?".

    The fact that E-Mail is so shitty is the sole reason Facebook has north of a billion users - for the simple reason that Facebook actually is a *better* user experience than E-Mail. Think about that for a moment.

    Bottom line:
    E-Mail needs a complete redo/replacement with hard asymetric encryption and zero-fuss key handling and exchange built in as a core specification. Top-notch FOSS clients for all major platforms included. That this whole field is in such a sad and sorry state is to the largest part the fault of us, the FOSS community.

    --
    We suffer more in our imagination than in reality. - Seneca
  10. Let me explain.... :-) by gjh · · Score: 5, Insightful

    This isn't entirely a mystery. For a technology to be widely adopted, it needs to be easy for everyone and provide demonstrable benefits. OR, it needs to provide benefits for a business who already has your custom. And there we begin to see the problem. There are two massive disincentives:

    - Crypto doesn't play well with webmail
    - Encrypted email can't be scanned for advert keywords

    So you will never see the likes of Google or Microsoft championing this. Apple - just maybe, as they would rather promote devices, and I gather they actually DO have decent end to end crypto on iMessage and so on. But even then, it's VERY hard to do in a way that customers would actually appreciate. No-one wants to get email working 95% of the time. It needs to be 100%. If you can't read 5% of your email, you're in trouble. Or you can't read email on the 5% of time that you need to access from a borrowed PC.

    It seems to me that the keys to making this work are:

    - Concentrate on signing before crypto. Get banks to sign email. Have different security levels; get to a stage where by default, only signed email will download embedded images, make links clickable without a warning, etc..
    - Find a way to make it work with webmail. Can we do this with JS? Or do we need browser support? End to end crypto It would require a way for a part of a page to be sandboxed, accept a secret to decrypt your keys, and not allow the plaintext info out. End to end signing is a little easier. This might also include retrieving the private keys from a distinct cloud service.
    - Solve the centralized trust issue. Probably derive a format from S/MINE rather than GPG for email, but critically, signing of certs needs a community trust system so you can see who trusts who, and people can get their identities signed by people they know.

    Finally, if that's widely deployed for signing then people can begin to encrypt with a hope of the other end being able to decrypt.

  11. Blame email clients by DrXym · · Score: 4, Insightful
    The first mistake made by email clients is they added support for a broken-by-design protocol called S/MIME which used asymmetric encryption through the entire message and was thus cripplingly slow. The ciphers were also covered by patents and had weak key lengths. Messages were signed with a cert like https, and were required to be signed by a CA. And you couldn't get a key unless you paid a CA for one. Oh and keys expired meaning you might have multiple dead keys to maintain if you wanted to open an old email. And no email client or ISP actually offered to give you a key or set you up with one so you had to figure this all out for yourself. And functionality like search / filtering broke on encrypted mail because the client never bothered to maintain an encrypted index of the plaintext that could have allowed it to work.

    Then PGP / GPG solved a lot of this bullshit, starting with generating keys for free but email clients never bothered to give it proper support. Instead they offered up some plugin APIs and unsurprisingly PGP / GPG ended up with half assed implementations too. Even fairly good extensions like Enigmail didn't integrate with the client as closely as they should.

    And by this point cloud based email took off and crypto fell by the way side. If you want to use crypto in GMail then you have to cut and paste and clearly it's too much effort.

    So I really don't blame GPG here. If the first thing an email did during setup was ENCOURAGE a user to create a key; and by default published that key; and attached the key sig to outgoing emails; and automatically looked up incoming email addresses; and automatically encrypted content when all recipients had their own key; and didn't hobble functionality for any of this (e.g. search still worked). THEN this wouldn't even be a problem. Encryption would have been the default and it would be an irrelevance if it was PGP or GPG was under the covers.

  12. Re:Metadata by Zero__Kelvin · · Score: 4, Insightful

    You clearly don't understand what GPG does, what Metadata is, what the phrase "nearly useless" means, or all three. You may as well have claimed that the 4th amendment is pretty useless because they can still see who lives there, and who enters and leaves the premises.

    --
    Guns don't kill people; Physics kills people! - John Lithgow as Dick Solomon on Third Rock From The Sun
  13. Re:I use GnuPG by CronoCloud · · Score: 4, Informative

    PGP isn't a standard

    It most certainly is:

    RFC 1991, 2440, 4880, 5581, 6637, 2015, 3156

    http://en.wikipedia.org/wiki/P...

    The e-mail client I use has gnupg support by default.

  14. Re:get to work by chihowa · · Score: 4, Insightful

    And, of course, the whole thing is dependent on fixed servers which Moxie claims aren't easily replaced. Just like TextSecure on Android depends on Google's servers to function.

    So the advantage over GPG is that the entire communication process can't be abstracted onto any other communication protocol (GPG on email/SMS/paper slips/etc), but depends on rickety infrastructure provided by somebody else. Progress!

    --
    If you want a vision of the future, imagine a youtube comments section scrolling - forever.
  15. Re:GPG is another TrueCrypt? by Martin+Blank · · Score: 4, Interesting

    Not remotely. He's encouraging good encryption, but calling for some updates (it hasn't significantly changed since the mid-'90s) and a better wrapper. GPG is still largely by geeks, for geeks. I couldn't get my parents to use GPG because they'd dismiss it as too hard, even if one of them is happy to stick it to the man. The suggested minimum settings vary based on where you look and when they were posted.

    Example: An RSA key size of 2048 bits is largely considered secure, but NIST recommends 3072 bits for anything that one would want to keep secure into the 2030s. People still often see their e-mail as their private papers and may be concerned over who can read them well past the 2030s. But does that mean they use 3072, or go with the random crypto weblog guy who says to always go with 4096? And why can't I create 8192- or 16384-bit keys like that software claims to over there?

    And what to hash to use? Plenty of sites still say MD5, but they were written years ago. Some have updated to SHA1, but others point out weaknesses there. OK, SHA2, then. But then there's SHA256, which must be better, right? (I know SHA256 is a subset of the SHA2 family, but those unfamiliar with crypto will not.)

    Until GPG-style crypto becomes relatively automated, it won't be embraced by more than a handful of people. HTTPS is widely used because people don't have to think much about it. This has some downsides for poorly-configured servers and Superfish/Comodo-style backdoors, but browsers and other software help take up the slack by rejecting poor configurations. PGP/GPG were designed to reach near-perfect levels of encryption, but that bar is clearly too high for significant uptake. We should instead be looking for something that encourages end-to-end encryption that is good enough. We can build on if the underlying structure is properly designed, and as people get more accustomed to crypto in their lives, they'll be able to adjust to improvements.

    When the majority of communications are relatively well-secured, it makes it far more difficult for a surveillance state to conduct its operations. Perfect security can still be a long-term goal, but we need more realistic goals to encourage uptake in the meantime.

    --
    You can never go home again... but I guess you can shop there.