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Encrypted email is still a pain

incoherency.co.uk

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Re: Encrypted email is still a pain

#41

Post by tptacek »

NoGravitas wrote: post #36
tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

This is all true, but IM is not email. What I want out of email that IM does not (generally) deliver: 1) UI optimized for longer form messages. 2) Decentralized system where you can send to anyone if you know their address, which may be long-lasting and not tied to the fortunes of a single private company. I don't demand compatibility or interoperability with SMTP, but I also don't want to throw the baby out with the…

The modern messaging services agree with you. Nobody has completely nailed the UX for long-term long-form conversations, but services like Signal are designed with those kinds of conversations in mind.

At the same time: if you had to compare the UX of running a long-term secret conversation over Signal versus the UX of trying to reliably encrypt messages over email, no normal user would ever choose the latter.

Secure messenger UX will get better long before email will be reliably encrypted (that's cheating, because email will probably never be reliably encrypted, but even if it wasn't, messenger protocols are going to win this race).

Re: Encrypted email is still a pain

#42

Post by Ursium »

rhaps0dy wrote: post #29
Gaelan wrote: post #4

Ooh, I know this one! I think. Doesn't Apple Mail have this built in? I go to Keychain Access, choose the option to generate a key. Two clicks. Head to Mail, encryption options are there. Now, to import his key. Do some googling on that. Wait, what? Apple Mail supports S/MIME, not GPG. Competing standards strike again. If the other person has S/MIME, Apple Mail does have a very easy experience. I can't speak for the…

For Apple Mail there is this: https://gpgtools.org/index.html I use it (in El Capitan), it works really well, it's the first time I've been regularly signing my messages with PGP.

And 2017.1b2 is finally available for Sierra :)

Re: Encrypted email is still a pain

#43

Post by scotchmi_st »

tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

> why bother? Email is just one of dozens of messaging systems available to Internet users. Better to move sensitive conversations to things like Signal, WhatsApp, or Wire --- the double ratchet construction is designed specifically to make IM-like protocols secure even when conversations are sporadic and last months.

This makes me sad. There's something profoundly democratising about the idea of running your own email or XMPP server (or any kind of server, for that matter). It's something you're in control of, that's configured the way you want it. Using someone else's server for everything brings with it a kind of tyranny (even if the people in charge promise not to use it for anything tyrannical (like that's ever happened)). If the response to that is "yes but it's hard/impossible to build a secure, distributed messaging system" then I think that's overly cynical.

Re: Encrypted email is still a pain

#44

Post by dijit »

Gaelan wrote: post #4

Ooh, I know this one! I think. Doesn't Apple Mail have this built in? I go to Keychain Access, choose the option to generate a key. Two clicks. Head to Mail, encryption options are there. Now, to import his key. Do some googling on that. Wait, what? Apple Mail supports S/MIME, not GPG. Competing standards strike again. If the other person has S/MIME, Apple Mail does have a very easy experience. I can't speak for the…

I'm glad S/MIME gets a mention because I've always been skeptical of it based on the fact that everyone rallies behind PGP.

I recently failed to install gpg2 on freebsd (for some reason it barks at me and fails and I don't care enough to waste my time on it) and decided to give S/MIME a chance with a signed cert from comodo. (which was free, just to try)

I have to say though the experience is beyond reasonable, it's very easy to get to grips with. If you're using S/MIME, I see a little verified badge in my client, not only that, if I've receieved signed mail from you, I can reply with an encrypted document that only you can decrypt.

This works with CC's and everything. The CA cargo-cult crap definitely has a benefit when it comes to web-of-trust.

(YMMV, I was using Thunderbird)

Re: Encrypted email is still a pain

#45

Post by drdaeman »

tptacek wrote: post #7

Encrypted email is pretty much over in 2017. The emerging consensus among experts is that it's not worth the trouble, or, worse, incapable of doing much more than generating a false sense of security. That's for a bunch of reasons: * An enormous installed base of clients that won't do encryption, meaning that at best you're attempting to tunnel encrypted messaging over an unencrypted transport. * A protocol that leak…

I think, the points about search and archival must apply to any communications medium.

If one isn't searching through their IM history but does so for emails, I guess, it should mean they just don't send anything non-ephemeral via IM.

(May be this is because IM has pool usability for any large bodies of text, while email handles those really well.)

Re: Encrypted email is still a pain

#46

Post by pmlnr »

tptacek wrote: post #22
pmlnr wrote: post #14

Earlier quoted context omitted.

> But: why bother? Email is just one of dozens of messaging systems available to Internet users. No, it's not. It's the only widely available, decentralized system, with which you can send to anyone, if you know the address. None of the big ones is this open. XMPP tried to address this and failed; now Matrix is trying again.

WhatsApp has over a billion users. There are big places where its market share exceeds that of SMS --- another big centralized service that has a userbase comparable to that of email. My conclusion is that the people who care about "decentralized" systems are a rounding error. I care about non-technologists managing to send asynchronous messages to each other that are well-encrypted by default. That's a solved proble…

> My conclusion is that the people who care about "decentralized" systems are a rounding error. I care about non-technologists managing to send asynchronous messages to each other that are well-encrypted by default. That's a solved problem.

You don't understand the problem: if you rely on a service like this, two things can - and by the laws of probability, will - happen:

a, a centralized service goes down and suddenly no one can talk to nobody b, you're unable to send a message to someone and never realize it

Imagine if there was _one_ ISP. One single mobile provider. If it goes down, it goes down everywhere, for everyone. Not fun.

As for b, I can't remember, but there's a term when a provider let's you post but it won't get show to others. They can also alter messages - see the Whatapp signal implementation issues that certificates can be silently re-issued.

You are, unfortunately right though: very few of us realizes how important this is. Thankfully the smarter elders of the internet seem to do. https://www.decentralizedweb.net/

Re: Encrypted email is still a pain

#47

Post by jvdh »

tptacek wrote: post #27
jvdh wrote: post #18

Earlier quoted context omitted.

There is still very much a set of users in the incident response community that relies on PGP. These are professional teams that need to communicate with each other. They talk about upcoming disclosures, current abuse, upcoming operations or patches, et cetera. This stuff is almost all short to mid-term secret. Most of this will become public in a month or so. Leaking meta-data is an assumed risk (or too much hassle…

I use PGP pretty regularly, too. But what does that have to do with the comment I wrote?

Encrypted email for this user group is certainly not over, and there is still no realistic alternative for it. So PGP is not going to go away completely.

Re: Encrypted email is still a pain

#48

Post by tptacek »

pmlnr wrote: post #46
tptacek wrote: post #22

Earlier quoted context omitted.

WhatsApp has over a billion users. There are big places where its market share exceeds that of SMS --- another big centralized service that has a userbase comparable to that of email. My conclusion is that the people who care about "decentralized" systems are a rounding error. I care about non-technologists managing to send asynchronous messages to each other that are well-encrypted by default. That's a solved proble…

> My conclusion is that the people who care about "decentralized" systems are a rounding error. I care about non-technologists managing to send asynchronous messages to each other that are well-encrypted by default. That's a solved problem. You don't understand the problem: if you rely on a service like this, two things can - and by the laws of probability, will - happen: a, a centralized service goes down and sudden…

No, I fully understand the problem. If Google Mail vanished tomorrow, a pretty large number of people would probably stop emailing altogether. The number of people for whom that's true increases every year.

If you find that unthinkable, consider the bubble you might be living in. I appreciate that there are people that require a decentralized service for messaging and understand where they're coming from. I don't deny their existence. I simply think their numbers are much smaller than they appear on nerd message boards.

Re: Encrypted email is still a pain

#49

Post by dorfsmay »

parennoob wrote: post #16

Do any of these keyservers perform email verification? It would go a good way towards some kind of verification that a user's GPG key corresponds to their email. Otherwise, anyone can generate a key with any email address and push it up to the servers. The standard way of verifying it (key-signing parties) is somewhat difficult.

FWIW, although everybody talks about their new chat system, key verification is one thing keybase.io does well.

Re: Encrypted email is still a pain

#50

Post by lukegb »

cookie0 wrote: post #15

Your key is not importable :D $ gpg --import stanley.asc gpg: CRC error; C68D2A - 29357C gpg: read_block: read error: Invalid keyring gpg: import from `stanley.asc' failed: Invalid keyring gpg: Total number processed: 0 Edit: Your key is way too short.

There's a 2 swapped with a 3:

https://gist.github.com/lukegb/243952e51ee1f7f9b6e1ed4177421...

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