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Comment by moxie | Hacker News Reader

A lot of the comments I've been getting are in the genre of "well... but GPG works."

Yes, GPG is a powerful tool that makes some encrypted communication possible. But is it really "working" if it's the tool we've had for the past 20 years, and we still ended up in a world where surveillance is so ubiquitous and privacy is so rare? Having used GPG, it seems more likely to me that there are only ~50k GPG users in the world because of the product, not because of weak desire or need for private communication.

I'm not suggesting that there's anything "better," but that it's really sad there isn't. GPG isn't ever going to be anything other than what it is now, and I don't think that's the future we want for ourselves.

We could try to slap a GUI on top of it, but I don't believe great products are made that way. Good UX requires thinking about interactions all the way down to the protocol. The good news is that GPG has such a small legacy install base (literally on the order of ~50k users), that there's no reason to maintain compatibility with OpenPGP. When building new products, we can start fresh with modern cryptography, a modern protocol, and a modern design philosophy.

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GPG is way, way, way to complex for all but the 0.01% of people who are GPG experts. It's too complex for me - and I've read (and enjoyed) Applied Cryptography.

But, not having used it for a few years, I went to take a look again - list some keys, maybe SMS some friends to exchange fingerprints and sign their keys, etc... - I'm trying to recall what the relationship between PUB, SUB, UID, Key Fingerprints are. And how do I indicate that I trust a key and upload it back up to pgp.mit.edu?

And I consider myself a member of the 0.1% who at least understand the principals behind PGP/Public Keys/Private Keys/Web of Trust, etc...

So - if I'm having trouble understanding this without a couple hours of study, their is Zero chance that the other 99% of the population will ever be able to wrap their heads around the intricacies of PGP. Something else is going to have to replace it.

[EDIT - as an aside, I've spent the last hour trying to do a "gen-key" on my ubuntu host, and been prevented by lack of entropy - and yes, I've tried running tcpdump, tried egrepping every file on the system for a string, etc... Ended up on https://bugs.launchpad.net/ubuntu/+source/gnupg/+bug/706011 and the answer seems to be, "Find a machine that does have entropy, or install a hardware random number generator in your computer."

Please add this to the reasons why normal people never use GPG

Edit-2: It took about 25 minutes, but apparently between find / -type f | xargs grep wontfindme and sudo tcpdump -nnn not port 22, I managed to collect enough entropy to keep gpg moving forward. ]

apt-get install haveged

I'm not sure why you're being down voted.

haveged is an absolute essential for all servers

http://www.issihosts.com/haveged/

It's snake oil -- entropy isn't "depleted" in any meaningful way; once your kernel PRNG has accumulated enough entropy that you'd be comfortable using it to generate a crypto key it is not going to cease being suitable for that just because you continue asking it for random numbers.

/dev/random is an entropy estimating entropy pool

that means it will block when it estimates that you have "used up" all of the available entropy

you can check how many bits of entropy your kernel thinks are available easily

cat /proc/sys/kernel/random/entropy_avail

edit: i should have mentioned that there is some reason to argue against this behaviour but that doesn't change the usefulness of haveged for existing systems

Yes, but that's a reason not to use /dev/random, not a reason to install snake-oil products.

The random(4) manpage is unfortunately exceptionally misleading, and has sadly led to a small but non-zero numbers of products that try to use /dev/random rather than /dev/urandom.

Sadly, gpg --gen-key doesn't even give you this option - but that's (as noted above) another flaw in GPG.

> and been prevented by lack of entropy

This sounds like an implementation fail / lazy implementor. GPG shouldn't need more than 32 bytes of entropy (for keying AES-128 and then encrypting a 128-bit block of data repeatedly until you collect enough randomness.)

There has been a number of studies (http://www.2uo.de/myths-about-urandom ; I don't agree with everything but interesting reading anyway) showing that entropy from Linux random is not better than from urandom (once urandom has been properly seeded). For this reason, I patched my rndlinux.c GnuPG source code file to always use urandom. Makes key generation instantaneous. When a software is stupid, I don't want to install additional stupid software or comply with stupid instructions; I simply patch it.

I think that on linux, you ideally don't want /dev/urandom, you want a recent kernel and getrandom(buf, len, 0). From the manpage:

If the GRND_RANDOM bit is not set, then the /dev/urandom pool will be used. Unlike using read(2) to fetch data from /dev/urandom, if the urandom pool has not been sufficiently initialized, getrandom(2) will block (or return -1 with the errno set to EAGAIN if the GRND_NONBLOCK bit is set in flags).

Then again, that's probably not important if you interactively launch gpg on a desktop system that wasn't just installed a minute ago or so.

Entropy is a massive problem, especially on headless servers.

Timer EntropyD [1] can be extremely handy (as can the audio-entropy gathering)

[1] http://www.vanheusden.com/te/

HTTP is '90s tech. TCP/IP is '70s tech. There's nothing inherently wrong with that. 1400 lines of python that tries to pretend that an interactive program is a library is definitely a problem though.

How's about this: rather than a protocol-up rewrite, how about just writing a library-up rewrite? Write a ground-up implementation of (maybe a subset of) RFC 4880, with opinionated choices of default ciphers (a bit like NaCl). Make it a portable library that can be used on all the popular mobile platforms and from all the popular languages. That's a plenty big enough job, and would fix the concrete pain points with GPG without throwing out the good part.

> We could try to slap a GUI on top of it, but I don't believe great products are made that way. Good UX requires thinking about interactions all the way down to the protocol.

What kind of concrete things would have to change at the protocol level? Plenty of good products conform to existing protocol standards, and a crypto protocol that has survived years of use in a hostile environment is worth its weight in gold. The talk of "modern" seems very handwavey as a reason to throw this out.

> GPG has such a small legacy install base (literally on the order of ~50k users), that there's no reason to maintain compatibility with OpenPGP.

I find it hard to believe there are only 50k users given that OpenPGP is built into the package-management infrastructure that every Debian user uses, and is required on Maven Central which virtually every Java system uses. Yes, these aren't people who actively chose it or are even aware that they're using OpenPGP - but protocols are like that; they're infrastructure.

And as for your 50k, that may be a small number but they're the people who really care about privacy. Snowden is among them. If you're trying to spread crypto, those are the last people you want to alienate.

> Write a ground-up implementation of (maybe a subset of) RFC 4880, with opinionated choices of default ciphers (a bit like NaCl).

That's what PBP does:

- Code: https://github.com/stef/pbp

- A short (9:03) talk by the author: https://www.youtube.com/watch?v=Kl_gLMef1mI

Thanks for the link, looks like an interesting project.

> HTTP is '90s tech. TCP/IP is '70s tech. There's nothing inherently wrong with that.

Sure there is. For one, we were talking about encryption protocols. Those are not encrypted. The one that is encrypted, HTTPS, sucks (the whole CA system). So after Snowden's documents came out I would've expected more people to say "it's time to get rid of HTTPS". That hasn't quite happened yet, and I'm disappointed by that. In case w

As for TCP/IP, again, not encrypted, and they need to be. In case we've forgotten, TCP/IP and HTTP is what made it happen for the Internet to become a giant spy machine. That to me means they are broken.

We need to switch to something like CurveCP, MinimaLT, Noise, etc, that is encrypted by default at the Transport or even the IP layer. If we agree "encrypting all the things needs" to happen, then the current state of TCP/IP and HTTP is horrible, and we're not moving fast enough to replace them.

The fact that we don't yet have a good encrypted by default alternative to TCP/IP and HTTP/S is what will also bring us a world of hurt when the "Internet of Things" arrives in a big way, along with self-driving "smart" cars that can be remotely updated (and hacked).

The CA system sucks but what would you replace it with? The only remotely viable alternative candidate is the OpenPGP web of trust, and, well, see the article.

Transport is the wrong layer to do encryption (much as I'd love to see more adoption of IPSec) because encryption and authentication are inextricably linked. Suppose you can confirm that you're absolutely, veritably talking to 174.16.23.46, and your messages can't be read by anyone but them. What good does that actually do you?

TLS is, despite all the problematic cipher suites, fundamentally sound infrastructure - which is why it hasn't been replaced. The same is true of OpenPGP. We don't need new protocols, just better implementations - an equivalent of LibreSSL for OpenPGP.

> Suppose you can confirm that you're absolutely, veritably talking to 174.16.23.46, and your messages can't be read by anyone but them. What good does that actually do you?

In the current post Snowden climate, can't we agree that this is at least a good thing? The good it does at the most basic level is protect your communications from prying eyes.

Does it though? There's no point encrypting everything twice at two different layers. And if you use an unauthenticated protocol running over IPSec, you can have a dangerously false sense of security.

> 1400 lines of python that tries to pretend that an interactive program is a library is definitely a problem though.

Yeah, +1 for this. The lack of a proper GPG library is very strange.

I'm in the process of writing a Python program that interfaces with GPG right now, and I was surprised to learn there isn't an official GPG library. The closest thing seems to be GPGMadeEasy [1], which is an official library wrapper for the interactive program.

Since I need low-level key manipulation (writing out a key with known values), what I've ended up doing is using the BouncyCastle Java library[2] via a separate Java command line program my Python program can call out to. It works, but it's painful.

So, yeah -- what would be the cost/benefit of the project lmm proposes to create a real, portable GPG library? It makes a lot of sense to me.

[1] https://www.gnupg.org/%28it%29/related_software/gpgme/index.... [2] http://bouncycastle.org/

My mother literally did not know how to turn on a computer until a few years ago, but was able to use Signal on her iPhone after almost no explanation. My mother looked at me funny when I tried to explain GPG to her after the Snowden revelations started. But ever since I installed Signal on my mother's iPhone, I have been able to have private phone conversations with my mother. The significance of these types of distinctions between gpg and Signal are hard to underestimate when you extrapolate them to a societal level. My partner uses TextSecure/RedPhone with ease, and most of my friends use WhatsApp. I've only been able to convert a few of my non-technical friends, in contrast, into gpg users. Another way to think about this in terms of strategy: the means actually are the ends.

Almost as important as his crypto expertise, moxie's deep understanding of UX and especially barriers to entry and the network effect have concretely made the world a better place, and not just for people like us...but also (and especially) for people like my mom, my partner, and my (mostly non-programmer) friends. Thank you for understanding that their privacy is important and that their human dignity matters--and especially for meeting them where they are.

As a result, now it's not just my colleagues "in tech"--but also essentially all of my friends and family--who are with you!

Just a question, how do you know it's only your mother you are talking to? Have you verified the key she uses with the one you are talk to?

It usually goes something like "mom, what are the two words (short authentication strings) you see on your phone?" Sometimes she even asks me--we make jokes about the combinations.

And yeah, it's true that some of the Snowden docs reference ZRTP attacks & spoofing voice so it's not necessarily foolproof (or her phone could be owned etc.), but another one of the things my mother told me when I was a kid was "the key is to begin." And that's what moxie's done...

What do you think that looks like, though? Is it TextSecure on the desktop, with file attachments? Is it Pond? Is it just email, but with a different crypto layer?

I feel like a lot of the things GPG aims to do are fundamentally hard. It's not the technology that sucks, it's the problem. I completely agree that the answer will come from thinking about user interactions first, but I'm not sure that the solution will look much different than a better GPG client.

I don't have a definite answer. There's the path we're executing on at Open Whisper Systems, but there are a bunch of other projects working in this area as well (Mailpile, LEAP, etc).

I think the problems are solvable, but only if we have a different design approach. So when I see projects trying not-PGP, I'm interested. When I see projects building on PGP, I'm less interested.

I'll take the opportunity to say that it saddens me that I still can not communicate using TextSecure with iOS users. It's been almost two years[1] since iOS support was "promised". TS is great, but we need to be able to communicate with iOS users.

[1] https://whispersystems.org/blog/sure/

Signal 2.0 was tagged on github 3 days ago and will bring the textsecure protocol to iOS whenever apple is done reviewing it.

If this is true, it's awesome. I've tried making contact between Signal on iOS with TextSecure on Android before, without luck.

Not the place :/

What do you think of Peerio?

Also, any vague timeline available for arrival of the desktop Signal version? What about video-chat support? Would that be possible with WebRTC? (although you should probably wait until ORTC is supported within WebRTC - v1.1 I think?) and then add ZRTP on top of it. Or is a desktop, Javascript version, just not secure enough for that to happen? What if you do it like Whatsapp's "web app", that basically only connects locally to the phone?

> It's not the technology that sucks, it's the problem.

This is my feeling as well. To optimize for security and privacy, it seems like it needs to be difficult by design. If it's too easy, it's probably less secure.

I'm not sure if anyone has given it seriuos attempts to make it more user friendly, though? Would be surprised if no one has, there should be a great opportunity here. Escpecially now that it has so much focus.

I also believe that some complexity is inherent to secure communication, so people are required to learn a little to properly use this. Hopefully, this will be taught in high school or earlier at some point.

However, I also (like Moxie) believe PGP is not at the sweet spot. It has too much complexity for the most popular use cases. Thank you Moxie and others who are searching for the sweet spots.

Peerio might work, but it hasn't been vetted too much yet:

http://peerio.com/

It's made by the CryptoCat author, so make of that what you will.

No linux support, no firefox support.

Literally the second tweet on their twitter account is 'Damn, it works. Got a lawyer who resisted all other methods to encrypt our comms with @Peerio. Big score for usability. Bravo @kaepora & co.' which kind of bugs me, too.

Back in the 90's I tried to use GPG, and I tried to pay for digital music. They both went roughly the same way.

Arguably it was easier to use GPG back then than it is now. Pine was my MUA and I had an easy to find public key. Now I have an iPhone, don't use Linux on my laptop anymore, and make heavy use of messaging products.

Here's what I have now that I didn't have then, 2FA. There's an app on my phone that makes it super easy so I use it. If I had to still carry around a separate RSA code generator I probably wouldn't.

Surely we can figure out a way to make encrypted email nearly transparently easy with the major mail providers, and the default mail apps on our laptops and and phones. Surely we can figure out a way to make a trustworthy distributed keystore.

Perhaps this will all change because before Snowden we were blissfully unaware and GPG was a cool toy unless your life was in real danger, post Snowden we're residents of a vast internet police state and my Mom knows how Target was hacked.

I have a strong suspicion we will figure this out, and soon. I wonder, are VC's are looking into funding easy to use consumer encryption?

>Perhaps this will all change because before Snowden we were blissfully unaware

Every time I see this in regards to email, I'm puzzled. Carnivore was known about in the 90s. Then there was the AT&T Room 641A in the 200s. So I don't know how people were unaware that state level actors could tap connections and record email.

Second, for this threat model, just forcing and validating TLS on SMTP gets you pretty far, does it not? You're then mostly trusting your email provider. And without trusting them, we get into user-unfriendly stuff like not being able to forget your password. (Barring some sort of breakthrough ideas.)

Seriously, has there been any good proposals that provide strong privacy (say, no one but the user can read the message) but aren't complicated or require users to do things they aren't gonna do: validate keys? PGPFone and ZRTP are great because you already have an "out-of-band" key auth mechanism in place, and it's fairly straightforward to check.

Re: "You're then mostly trusting your email provider. And without trusting them, we get into user-unfriendly stuff like not being able to forget your password."

Nobody should trust their email provider if they are concerned about the privacy of their email. The Job To Be Done, by an email provider such as gmail/yahoo/hotmail is to act as a mail store, and mta. A user should be able to rely on a local MUA for confidentiality. Admittedly, that shifts the level of trust from the Email Provider to the provider of the MUA software and the Local Hardware, which is why things like OpenBSD/Linux and (hopefully not firmware-tweaked) commodity hardware is so important.

What your proposing is currently limited to people that are more-or-less OK putting up with PGP. For everyone and their mom to use encryption, features like "I forgot my password and now lost all my email" aren't acceptable. Nor are things like "I've got to make a separate, verified, out-of-band contact to verify that I've got the right key".

I'm hoping someone comes up with a breakthrough idea here, something fantastic that enables real privacy with no inconvenience. But in 20 years, there's been essentially zero progress on that front. All proposals either violate Most Users' required features, or boil down to offloading trust to the email provider.

I don't see any way to protect users against forgetting their encryption passphrase, or losing their private key, without offloading trust somewhere. Except for backups, anyway.

It can be very hard to know whether you have the right public key, especially for people that you know only from online activity. And it's not uncommon to find multiple unrevoked keys, with the same email address.

But check out https://keybase.io/mirimir. You can easily get a GnuPG key that signed proofs in my profile here, on GitHub, and on reddit. Also, the email address in my key is linked to a Gravatar that StackExchange and other sites use. So whoever I am, you can be confident that I control that GnuPG key.

> I don't see any way to protect users against forgetting their encryption passphrase, or losing their private key, without offloading trust somewhere.

Private keys are obviously an issue, but I don't really get why passwords are considered so important.

I like to use GPG when I can for communicating with people, but most of the things I put on it are less private than what you would get if you got my computer.

I don't think passwords protect you if the attacker can install a keylogger (correct me if I'm wrong), so anyone with hardware access or malware isn't going to be stopped. You are only protecting against people that can read files from your computer but not install hardware/software.

I think for the average user the password provides little extra security while having a high UI cost.

My mom didn't know about Carnivore. I did because I worked at an ISP. My mom knows about Snowden. Thus the general public was blissfully unaware, now they are not.

To be technically precise what makes 2FA easy to use is that all services are web-enabled and issue you a temporary-long-term token (ie a cookie with a session id).

If you had to open an app on your phone at each login you'd get crazy real fast :)

I do like your analogy tho. Digital music is a breeze to buy nowadays. Moxie seems to appear as covertly saying its misguided to donate money to GnuPG so that it finally gets good, because, you know, not-moxie-made.

The.. what was it called? Redphone? Whisper? and various other projects - while very cool - didnt achieve even as much popularity as GnuPG (which in itself is far from greatly useable).

I know of one tech that has a chance right now and thats U2F/Fido. It allows for building a framework (being GnuPG or otherwise) around it that's both secure and works for everyone. Why? Because fucking gmail supports it that why. It has nothing to do with the actual tech. It has to do with support. It has to do with my iphone, android, whatever, working with it seamlessly. It a lot to do with "slapping a GUI" at the right places.

You say "Redphone? Whisper? and various other projects - while very cool - didn't achieve even as much popularity as GnuPG"

The Axolotl protocol that was created for Whisper System's TextSecure is now used, by default, by Cyanogenmod (10 million users) and the Android version of WhatsApp (more than 500 million installs from the play store).

I'd say Moxie's tech has been pretty widely adopted.

When can I have a compatible FOSS desktop client? I don't do 100% of my communications from my phone, and I never will.

If you can't do it on desktop, you can't do it at all. Mainly because some of us have real work to do.

If the only "usable" implementation is on a hard-to-physically-secure mobile device that uses a tonne of different uncontrolled network access points a day -- that's not really an option now, is it?

I feel you're missing open whisper systems' target audience. If you've seen how regular people use computers, their phone is the most secure device a normal person owns. Not the most secure if you're worried about targeted attack, but the best place to put a dent in cheap dragnet surveillance :)

You won’t have that until someone takes the time to produce such a client.

Its like saying notepad is a popular because its installed with Windows.

Even if you ignore Whatsapp and Cyanogenmod, you have 500,000 - 1,000,000 Textsecure installs according to the Play Store. That is on order of magnitude more than the GPG estimate of 50,000. In less than 20 years.

> Surely we can figure out a way to make encrypted email nearly transparently easy with the major mail providers,

What, Gmail? Yahoo? They exist only because they can read your plain-text email and serve ads against it. Most people get their email through free webmail providers, who have every reason not to make encryption easy.

Blaming "1990s crypto" is, IMHO, missing the point. Until we discover attacks against the ciphers there's no reason to throw them out just due to their age.

If you're referring to GPG's shitty interface, then sure. But how much of that is "1990s crypto" and how much is due to the fact that it's one guy working by himself and barely being able to afford it, for years?

GPG with Linux-levels of support would be an entirely different beast.

edit: oh sorry, are we not allowed to disagree with Big Names™?

>edit: oh sorry, are we not allowed to disagree with Big Names™?

Not when it comes to cryptography and HN. Moxie, Collin, and tptacek are the only 3 people that can say anything that isn't mainstream pop-crypto. Anyone that dares to disagree with them is clearly wrong and must be punished with downvotes.

I agree, and this attitude is one of the things that's holding progress in crypto back.

Should random software engineers experimenting with crypto claim that they've created a software package worthy of being used by dissidents and whistleblowers?

Absolutely not!

But should we be discouraging random software engineers from experimenting with crypto, and starting open source projects that may gain steam...and eventually, after years of use and audits, gain the standing and reputation to be used by dissidents and whistleblowers?

Again, absolutely not.

As it happens, I was just studying the CT-RSA 2015 conference agenda, I read that there is a conference talking about some form of oracles in OpenPGP and affecting several implementations. That would indicate that the RFC4880 format is fundamentally broken in theory AND practice. http://www.rsaconference.com/events/us15/agenda/sessions/176...

Well for one, he's blaming the protocols that are "90's crypto", not the cipher, but second, I think GPG does use some weak crypto as well, at least as options, and they never bothered to remove those.

Hey Moxie, it intrigues me that the first thing you mention in your post isn't technical or even about UX (which is what most people in this thread are focusing on). Instead, it's that you're starting to dislike reading emails from the kind of person who would "voluntarily use GPG".

I know you said there's no unifying theme to these emails, but can you elaborate? Maybe something about security-obssessed lay people using GPG to send the most trivial of emails? Or something else entirely?

To quote another commenter:

"Way to take a dump on people who make an effort."

It's the same as people who voluntarily use Windows. It says something about them, that's all.

I can guess why you're being downvoted, but your comment is ironically correct. It /does/ say something about them! But what that is depends on who you ask. And that, again, says something about /them/.

Which says something about the downvoters.

Irony everywhere.

People are getting offended, but I could have replaced Windows with almost anything. Our choices say things about us. Getting back to the subject at hand, though, I assume 'moxie meant that people who choose to use GPG for casual conversation must be slightly masochistic and therefore slightly less likely to have something interesting to say.

... just like Windows users ;)

Yes, of course, but I'm very curious about moxie's interpretation of what using GPG says about the people who randomly email him; certainly more curious than constructing my own stereotype.

Get out of your bubble. Windows is ubiquitous. It has 90% of the desktop market share. There is no generalization you can come up with about that many people.

I think the OP meant that, given a choice, say, of getting a Mac or a Windows PC at work, you voluntarily pick the Windows PC.

That's also a false dichotomy, a dangerous one at that. Sort of like two party system.

> Windows is ubiquitous. It has 90% of the desktop market share. There is no generalization you can come up with about that many people.

'People who use Windows do not have both the intelligence not to desire it and the power to do as they wish.'

It might be people who miss the forest for the trees. Right now Moxie is working on bringing encryption to the masses. That involves a whole-product view, with empathy for the unsophisticated (think about a kid who's only computing device is a phone).

I know stereotypes often treat people unfairly, but the kind of person who has the dedication required to use PGP seems, to me, to often coincide with the people who find fault with everyone who hasn't had the dedication or focus to learn sophisticated software techniques.

And, if I were Moxie, that would be a source of constant frustration to me. The very people who have the ability to make things better -at best- don't empathize with the people they could help, and at worst harbor a bit of contempt for them.

Considering Moxie seems to be dedicating a large part of his life's work to helping average people, I believe the attitude I described could play foil to the inspirational messages he also receives. But I don't pretend to know him or anything.

> Considering Moxie seems to be dedicating a large part of his life's work to helping average people, I believe the attitude I described could play foil to the inspirational messages he also receives. But I don't pretend to know him or anything.

You may say that, but after the "we specifically work to make TextSecure impossible without Google Play because using Android without google is 'going back to the old broken desktop security model'" thing, I'm not convinced.

I'm sure moxie is good with crypto, but sadly, he's on different side of war on general purpose computers than I am. He's on the side of walled gardens and limits what can you do on your own device, and I can't accept that.

EDIT: and of course he would spit on GPG. For moxie, GPG is competition.

Moxie's stance on non-Play releases is not as extreme as you suggest:

https://github.com/WhisperSystems/TextSecure/issues/127

I am - roughly - a GPG fan. I've done classes on it, used it at work and at home, etc.

GPG is a terrible UX. Accidental use of GPG tends to fail open, and insecurity results. Futzing with different keys, rotating them, retracting them, etc, are grievous. I can't reencrypt old stuff to new stuff (e.g., a pw database) without spending a good deal of time thinking about attacks, file safety, etc.

I'm really a distributed encrypted email fan, I guess. I want to securely communicate over email to my friends and family, without having to do the GPG dance.

Why 50k users? PGP/GnuPG is used to secure a _lot_ more than email.

Every Linux distribution signs packages with it. So that's at least 100M users right there. Several APIs regarding domain name and AS registrations is based on it. I know at least two financial systems that signs their messages with it. That's just mentioning a few I can think of right now. I'm sure it secures a lot lot more. It's used all over the place and it seems to do the job fairly well in most cases.

Is it suitable for signing email in 2015? I don't know. Things could certainly be improved. I know there are more suitable schemes for IM communciation. But the software and the underlying protocol is not something you can break in a heartbeat. It's important software.

Perhaps we need to speak more of the evolving use case in email?

You misunderstand, they are talking specifically about encrypted communication for the new use case. Think of it instead as trying to replace email for unencrypted communication, you need a different use case as the user base is too entrenched. In contrast GPG encrypted messages are a small community.

The fact that GPG is used for other things is fine, as it will still exist and can still be used for those things.

I think you are blaming a slightly arcane program for what is essentially laziness of the population. Every time I read a comment on HN stating how PGP isn't usable I cry a little bit inside. GPG in no harder to use than git or many other tools professionals use.

The difference being, its worse to make a mistake using GPG than it is to make a mistake using most other programs. In the end, you are securing confidential information, which will always be hard, unnerving and require concentration and care. And this is just inherent to the task, which is fighting an undefined, super-powerful, ill-meaning enemy.

Encryption is violence. The objective is to violently keep an enemy away from your jewels. Instead of using an armed guard at your door, you use mathematical forces which are impossible for your enemy to overcome. Imagine your enemy needs the cleartext to save his own life, how does he feel when he is denied access and unable to gain access? It doesn't matter if its a steel door or a block-cipher.

What people are essentially demanding when they want "easy to use crypto" is a self-firing and self-aiming rifle with friendly-fire detection. "Keep all my adversaries away but don't bother me about it."

That's not how conflict works. If you attempt to secure your communications from a state actor, you are engaging in a full-blown combat against one of the most deadly forces there can be. That conflict will always be demanding and unpleasant. GPG being "hard to use" will be the least of your problems.

But no, we want everything for free. Protecting yourself against the overlords should be easy and painless, almost automatic. The defendant shouldn't have to learn how his defense works or how to properly use it.

Seriously?

EDIT: And what I find unnerving about your post is, suddenly the people who put in the effort to use GPG are the bad guys? The 0.1% who actually take privacy seriously enough to go through the the trouble? Don't get me wrong, I almost never use GPG, not because it's hard to use (M-x epa-encrypt-region, anyone?), but because I don't want to experience the emotional distress related to struggling with a super-powered state.

Consider a separating the goals.

OTR is much more successful because it allows ad-hoc connections instead of trying to make authenticity guarantees. It encourages authentication, but the decision of when to invest that extra effort is left with the user. Fundamentally, OTR just offers privacy from eavesdroppers, and it does that well. Every other feature is extra. Even better, these new features (e.g. authentication) don't have to start from nothing. A big benefit of separating features is that is added later can leverage the existing infrastructure.

I personally believe the "killer crypto app" that will actually be adopted is a tool that is the opposite of OTR. It should only promise ad-hoc authenticates and do it in an generic style. I mean something that is somewhere between "gpg --clearsign" and 2channel/4chan style tripcodes[1]. In an ideal world, this needs to have a clearsign-style mode, so it can be used on existing forums. If the browser simply offers a "sign this" button next to textareas (no password, auto-gen they key and stuff it on a keyserver, just make it happen), it will be used. On the decode side, any blocks of text the browser sees that look like a signature get check, with the key pinned. That's it. Any features that allow nicer integration with email, forum software, etc, are nice but optional.

This provides a minimum, anonymous level authentication (forgery prevention), and the only UX the user should have to see is the "sign this" button and a loud "possible forgery" warning if a signature doesn't match the pinned key. It even works regardless of who is transporting the message (different websites, email, gopher, avian carriers) without needing an "identify provider". Upgrading this infrastructure of pinned keys into something more interesting can happen later on, if desired.

Would this work? I believe it's worth trying. It is clear that trying to solve all of the security needs in a single tool has not worked, and the one tool that got any adoption at all (OTR) has a much more narrow set of goals.

[1] http://en.wikipedia.org/wiki/Imageboard#Tripcodes

What would be needed for adoption and ease of use would be for a registry to store public keys and salts... for webmail, a section of the message could be labelled as something like...

    [[SECURE_CONTENT abc@ez.im -> foo@bar.com
        BASE64-CONTENT
        =====
        BASE64-SIGNATURE
    ]]

The a browser or email plugin can then retrieve the public key for abc@ez.im and confirm the body was sent by who it says it was. Then if the user has already connected via the plugin, their private key is used.

For simplicity the registry will do email validation of its' users, it should issue a SALT so that PBKDFx(SALT + email + passphrase) is used to generate the private key... the public key is stored in the registry.

For more control, a given service entry in dns for peer-crypt registry for the given domain can be set as an authority. A distributed system could be used for confirming tokens combined with DNSSEC as a control system for greater availability.

There are flaws with this idea, but it could be something that can be made insanely easy to use, as well as adding a lot of security to email transmission without creating an all new infrastructure, only adding services on top of what exists.

For power users, they could set the public key without salt in the registries, if they wanted to manage their own, instead of relying on the generation mechanism, or to use/keep the same key across different addresses/providers.

>The a browser or email plugin can then retrieve the public key for abc@ez.im and confirm the body was sent by who it says it was.

Well, that's the issue, right? How does it do this?

OK, GPG is crufty and hard to use, and the email protocol exposes metadata. So perhaps it is best to start fresh.

What do you think of the Dark Mail effort? And of Pond?

Please do this! I'd love to be able to use encrypted communications as a matter of course, but just not enough of the folks I work with are able to get it set up. My world is filled with smart people, but only a small fraction are purely computer folks and to try and get a biologist to understand why it's interesting to have all emails encrypted is a losing task unless it's super easy.

I relly disagree that all is lost for PGP. Here's why it's a good idea to not just carelessly toss out the seemingly old and busted: https://blog.whiteout.io/2015/02/25/pgp-theres-life-in-the-o...

If it's not weak desire or need for privacy then why hasn't the market successfully solved this? Moreover, where is the outrage at the lack of privacy.

>We could try to slap a GUI on top of it, but I don't believe great products are made that way.

I'm right there with you on that one. So is most of HN I imagine.

But the Apple ][ really brought the PC home for so many more people than it's competitors purely because of it's relatively simple GUI.

Command prompts scare the average user.

The Apple ][ booted to the commandline, as did the ][+, //e, and //c.

At least the //e could boot to a disk without any interaction with the command line.

I guess that's why I will always be a C=> fan.

Don't you think the time is right to build such a system?

Public awareness of privacy especially wrt mass government surveillance, identity theft and high profile corporate breaches seems that such an thing is ripe.

I am naively optimistic given the right implementation a consortium of stakeholders could do something meaningful.

One of the biggest problems with GPG is keyex. Sure, we have key servers, but that's not really a secure way of doing things.

Secure communication is as much a cultural change as a technological one.

GPG at least has the web of trust, with all its privacy problems. Most technologies just use "trust on first use".

That doesn't actually solve the problem though. It helps in theory, but it requires the user to understand what they're doing to a level most won't.

There is also the cultural issue of just exchanging fingerprints. Only techies put them on business cards, and even then only some. It needs to be common action.

Well, at least they try to solve it.

Another approach for verification is employed by Threema [1]: The server verifies email addresses and phone numbers, so if the address or number is in your contacts you can have more confidence, represented by an orange dot next to the contact. If you verify the fingerprint by scanning QR codes, you get a green dot.

About fingerprints for the masses: I really like the visual fingerprints Peerio is using (basically bigger Github-style generated avatar icons).

[1] https://threema.ch/en/faq

> When building new products, we can start fresh with modern cryptography, a modern protocol, and a modern design philosophy.

Agreed 100%. I just don't have anything to offer in this space :(

Is anybody trying to implement identity-based encryption?

You say "cryptography of the 90s" as if the cryptography part of GnuPG was old and therefore unusable. This seems to be quite misleading to me.

Couldn't agree more. I have public keys available and I understand the concepts at a high to medium level but if it's taken me as long as it has to get a grasp on it (And I still would need to do a number of google searches if I received an encrypted email) how can I expect all of my friends to ever get it? They want something that "Just Works" and so they gladly use (as do I) Facebook, iMessage, SMS, and Email. All unencrypted (Well iMessage is encrypted but I know they could easily view any messages they want). They still have password-reuse issues all over the place (my hands aren't clean either).

It's not that I don't care about privacy, I very much do, and my friends care as well (to a slightly lesser extent I would say and I'm willing to accept more to get to that point than they are). It's just that I am completely overwhelmed, only 1-2 of my friends even understand encryption at a high level and none of them expose private keys for communication. Even other developers I worked with got annoyed with OTR with adium/pidgin to the point I had to turn it off. It's not that I want to throw in the towel, I desperately want a solution, but even easy to use (what I'm looking for) "secure" communication tools get torn to shreds here on HN and so I haven't even considered trying to get them all to switch tools (even I thought it was possible, which I don't).

I guess what I'm trying to say is I'm not going to stop talking to my friends and my friends more or less refuse (due to complexity) to use encryption so what is the purpose of me even trying? The end result would be what? Maybe 1-2 people with which I can talk securely? Now I have to have 2 workflows and even if I have super-secure unique PW's, FDE (Full Disk Encryption, which I do use), and take steps to secure all MY data all of my friends are essentially leaking my data. So if the NSA/FBI/China/Hacker/etc want my communications they can just go after the weakest link, the people I talk to. It's very disheartening to say the very least.

I've considered blogging about this a number of times but didn't want to get destroyed here on HN (if I even posted it here, I probably wouldn't due to backlash) for being defeatist or get told how I am the problem. I am not a cryptographer and therefore am not qualified to even attempt to build secure software (if I even thought I was capable of coding up such a project). Even the tools that are easy to use that DO use tried and true encryption (Like PGP gmail/chrome extension, that's all well and good but what if I'm on mobile? Or on a friends computer? It's just too restrictive) are locked to a an OS/Browser/Device. I really do understand I'm asking for quite a lot (Cross-platform AND cross-device) but without those "features" there is no way I could get my peers to switch.

I'd love to have someone reply with how wrong I am how there is X tool/product/service that satisfies my requirements but I've searched high and low so I don't expect such a reply...

You know you're one of only a few people in the world who is in a position to do that, right? Anyone else would (rightfully!) get torn to shreds on HN by tptacek or yourself. And I say "rightfully" because it is very likely that other people would screw up some central aspect to the security of any new product that claims security.

It's not just that, though. Anyone else with your knowledge but no standing would be scorched for saying what you just said. "Throw away the one thing that has proven to be secure and write our own protocol" doesn't go hand in hand with "serious cryptographers trust what this person is saying."

The truth is probably that either you do this or nobody will.

You should. The world would be better for it.

Is there a kick starter page for this cause that I can contribute to? Because I would.

I'm not going to back just any crypto project, but with the right people leading the charge I would get behind it.

https://whispersystems.org/blog/bithub/

(Unrelated to GPG, but this goes towards crypto projects by Moxie and other solid people.)

Go through my comment history. How many comments do you see? A handful? Yup. The reason there are so few is because, I only reply to comments I wholeheartedly agree with. And this is one of them.

> You know you're one of only a few people in the world who is in a position to do that, right? Anyone else would (rightfully!) get torn to shreds on HN by tptacek or yourself. And I say "rightfully" because it is very likely that other people would screw up some central aspect to the security of any new product that claims security.

This attitude is why GnuPG (and other PGP implementations) are in a position to be criticized by the Moxies of the world. Is there some particular reason why anybody outside of some recognized elite should be discouraged from at least trying to create a better, improved system? Yeah, they'll probably fail in a lot of cases, but if the world really wants a modern, easy-to-use alternative to PGP (a real alternative, not use-case-specific alternatives like RedPhone and TextSecure; encrypted/signed email is still a valid use case that both those things blissfully ignore, by the way), this sort of attitude - that anyone outside of a select few rightfully deserves to be scolded for trying to make better crypto - is lethally toxic to that goal.

Yes, there is a reason to discourage those people.

In between the time that a cryptographically illiterate developer releases their MVP 1.0 version and the time that it's discovered that their cryptography is fundamentally flawed --- a window of time that can stretch on for years --- actual people will rely on the tool for their security, not realizing that serious adversaries are reading their messages.

Most new cryptosystems --- a cryptosystem being "anything that uses a cipher, including when the cipher is simply AES --- are terribly broken.

Search for [decryptocat] for an extremely good example of what I'm talking about.

Developers who are new to cryptography that want to learn more about it and eventually use it in their own systems should start by learning how to exploit broken cryptography. If you can't exploit an RSA padding oracle, you shouldn't be designing systems that use public key cryptography. If you can't exploit a CTR nonce stutter, you shouldn't be using block crypto.

Developers who don't want to learn cryptography should work on improving the UX (UI and workflow) of existing cryptosystems. PGP could sure use some help, but even if you don't want to help with PGP, there's a huge green field of work to be done on browser TLS trust and CA user interface. Just as one example.

My point is that this attitude of "only people who have proven themselves as cryptography geniuses may dare to think about thinking about cryptographic protocols" also discourages the potential UX/UI/workflow/etc. programmers from participating, since it gives the impression that their contributions will never be "good enough" to be accepted. It also discourages potential developers of the crypto algorithms and protocols themselves from participating, even if they have gone through the (in your opinion) requisite experience of learning how to break existing cryptosystems, because of the fear that they'll just be burned at the stake by the rabid likes of Hacker News and Slashdot for daring to suggest anything new (these are the sorts of cryptographic programmers I'm talking about, not some "badass rockstar ninja" Macbook-toting YCombinator-funded Ruby.js hipsters manufactured in the heart of Silicon Valley like you seem to be implying).

This results in things like GnuPG being considered hard to use. This results in things like GnuPG struggling along with a single core developer and barely enough funding to support that developer (even now). This results in things like OpenSSL being horribly undermaintained, to the point where nasty bugs like Heartbleed are allowed to exist longer than they should because there is an insufficient quantity of eyeballs to find them and squish them. It doesn't take a rocket surgeon or a cryptographic guru to see that this is nothing but an awful situation for pretty much everyone involved.

what's a CTR nonce stutter ? Its not listed on the cryptography attacks wikipedia page: http://en.wikipedia.org/wiki/Category:Cryptographic_attacks

i think any 3rd party distributed crypto is only useful against weaker adversaries (weaker than the person doing the distributing). For p2p crypto designed and agreed to by the two parties, there are lots of options, starting with a 1-time pad, CTR mode hash based ciphers, etc...

That Wikipedia page is not very useful.

Do you have any specific criticisms of GPG other than "it's old and it's not popular"?

What's your ideal vision of what end-to-end encryption for the common (wo)man should look like other than "not GPG"?

Two questions whose answers are nonexistent in your article.

Specific criticisms of GPG:

> the working hypothesis for privacy enhancing technology was simple: we’d develop really flexible power tools for ourselves, and then teach everyone to be like us... 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

I think it's self-explanatory why it's not good that users need to know about SERPENT, IDEA, and TwoFish.

> the fundamental architecture of PGP also leaves no room for now critical concepts like forward secrecy.

> a ballooning penumbra of OpenPGP specifications and notes so prolific that the entire picture is almost impossible to grasp... Mailpile had to write 1400 lines of python code just to interface with a native GnuPG installation for basic operations, and it still isn’t rock solid.

> journalists who depend on it struggle with it and often mess up (“I send you the private key to communicate privately, right?”)

UX failure leads to user uncertainty or insecure behavior.

What a better replacement looks like (from the comment here):

> Good UX requires thinking about interactions all the way down to the protocol.

> we can start fresh with modern cryptography, a modern protocol, and a modern design philosophy

> UX failure leads to user uncertainty or insecure behavior.

I'd say user uncertainty and insecure behavior are, each, sufficient criteria to declare a UX a failure.

You list plenty of specific problems with GPG the UI and GPG the "API" (though frankly the fact that mailpile would write 1400 lines of python that wrap GPG rather than taking one of the independent library implementations of RFC4880 and bringing it up to production quality makes them part of the problem). But none of those specific problems are problems with OpenPGP the protocol.

Well, I was only quoting the article, but it sounds like he has a good point that the protocol doesn't support forward secrecy. I also tend to trust his judgment that it's too complicated, and/or the complication adds little value for "normal" users. I guess some of this can be isolated as an app/API problem rather than protocol, as you say.

Perfect forward secrecy is of course better than not, but I'm not convinced it actually helps a lot for realistic threat models. It means that when you utterly screw up and reveal today's treason you won't also be revealing last week's treason - but for someone who's using crypto for serious reasons, how often is it that last week's message would get you in trouble and today's message is innocuous?

Would a ground-up rewrite of OpenPGP have PFS? Of course. Is the functionality important enough to justify a new protocol? Not on its own, IMO.

Follow-up: on more thinking, I don't think it's possible at all without compromising important properties of GPG.

Thanks; for the first question, I suppose I should have read more carefully.

The second question, however, still isn't adequately answered; "we should be thinking about interactions" and "we should use modern things" are two of the most vague answers possible.

Apparently it's so hard to use properly that even Snowden screwed it up in the course of communicating during his leaks.

> The frustrating and ironic thing about GPG is that even experts make mistakes with it. Even, as it turns out, Edward Snowden.

> I now had Poitras’ permission to send Snowden her encryption key, but in his first email to me, Snowden had forgotten to attach his key, which meant I could not encrypt my response. I had to send him an unencrypted email asking for his key first.

https://firstlook.org/theintercept/2014/10/28/smuggling-snow...

Any encryption system has to exchange keys, and you can do it easily or securely, pick one. Failing the way you describe makes things cumbersome but does not compromise security.

Perhaps it would be better to leverage your position and your knowledge and come up with something before you write up a post like this? As other commenters have pointed out, you're in a prime position to actually come up with a working concept instead of just writing your opinion about it.

I don't open a link to Paul Graham's site to read "Shit's bad, guys, and here are some fairly shallow reasons why I feel I can make that statement". I go there to read something that's been thought out by someone 'in the know'. Same goes for when your name is on a post about crypto. This was just whining.

That may be totally acceptable to you, but I don't think I'm alone in expecting more than just an opinion.

In case you didn't know, Moxie is already doing that https://whispersystems.org/

In any case, your point still stands, generally speaking.

Yes, I was referring to the post itself, which is essentially just complaining in the end. I am surprised it reached the top of HN, considering it really adds nothing.

It's one thing to recognize the limitations of GPG. I think we all do. It's another to declare it an abject failure and continue to use it and complain.

Go generate a revocation certificate and push it to the global pool. You'll stop getting those disappointing emails.

But seriously, go build something better. I fucking dare you. We'd all be better off for it if you really did.

He does build something: https://whispersystems.org/

Whether or not that something is better, however, depends very much on the use case. RedPhone and TextSecure are designed for very specific use cases (phone calls and text messages, respectively), whereas GnuPG is designed to be general-purpose and universal regardless of use case. Most jarringly, neither of those programs address email or file encryption/verification, and thus do nothing in GnuPG's primary realms of usage; by comparing them, you're basically comparing apples and crowbars.

The issue is that it seems like you want to replace GnuPG by something that does the same - but is made better, and that has your brand name on it.

That's very marketingish of you. Why not fix GnuPG instead? There's more than slapping GUIs to things!

Also, where is your 50K user base number from? According to my SKS keyserver traffic, it's much greater, even if i were to assume 50% of the traffic is non-human.. what the fuck happened to you man?

Also, if it's well done - I'm not against something different from GnuPG. I just disagree with the argument.

Which leads to this question:

which product are you going to announce in 6mo that would be so much better?

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