3 ms·
So what do I use for encrypted messaging that can, like, replace email, then? Nobody seems to have provided any sort of satisfactory answer to this question.
by Sniffnoy 7y ago
So what do I use for encrypted messaging that can, like, replace email, then? Nobody seems to have provided any sort of satisfactory answer to this question. To be clear, an answer this has to not just be a secure way of sending messages, it also has to replicate the social affordances of email.
E.g., things distinguishing how email is used from how text-messaging is used:
1. Email is potentially long-form. I sit down and type it from my computer. Text-messaging is always short, although possibly it's a series of short messages. A series of short emails, by contrast, is an annoyance; it's something you try to avoid sending (even though you inevitably do when it turns out you got something wrong). Similarly, you don't typically hold rapid-fire conversations over email.
2. On that point, email says, you don't need to read this immediately. I expect a text message will be probably be read in a few minutes, and probably replied to later that day (if there's no particular urgency). I expect an email will be probably read in a few hours, and probably replied to in a few days (if there's no particular urgency).
3. It's OK to cold-email people. To text someone you need their phone number; it's for people you know. By contrast, email addresses are things that people frequently make public specifically so that strangers can contact them.
So what am I supposed to do for secure messaging that replicates that? The best answer I've gotten for this so far -- other than PGP which is apparently bad -- is "install Signal on your computer in addition to your phone and just use it as if it's email". That's... not really a satisfactory answer. Like, I expect a multi-page Signal message talking about everything I've been up to for the past month to annoy its recipient, who is likely reading it on their phone, not their computer. And I can't send someone a Signal message about a paper they wrote that I have some comments on, not unless they're going to put their fricking phone number on their website.
So what do I do here? The secure email replacement just doesn't seem to be here yet.
- lvh 7y agoDo you feel like PGP is a good way to cold email people in practice? (I'm not trying to put words in your mouth, but that sounds like what you're saying.)
- Sniffnoy 7y agoGood question. Not sure. Although I don't see why I wouldn't, if they have a PGP key listed? (I guess there is some question over whether the listed key is actually them?) But my point is that, well, email is a good way to do that, and Signal isn't, so I'm going to use email rather than Signal. Honestly, I wouldn't focus on (3), because as I see it, if you can replicate the feel of email, things like (1)-(2), so that it can replace email in contexts without (3), then (3) will just come naturally as it slowly replaces email. Edit: All this is assuming it isn't tied to a phone number or something similar, of course!
- simonh 7y agoHow does one list a public PGP key, is there a verified central listing service?
- meruru 7y agoYou can put it on your website or anywhere really. Some people use keybase.io for this.
- roel_v 7y agoThere used to be a bunch of those in the 90s and it was a mess.
- Leace 7y agoI guess they mean putting the key on a webpage or using Web Key Directory or a centralized service such as https://keys.openpgp.org https://keys.openpgp.org
- umvi 7y agoI don't get what's insecure about normal unencrypted email. It's sent over https, isn't it? It's not like I can read your emails unless I break into Google's servers, no? And even if I do, they probably aren't even stored in plaintext. I just don't get the encrypted email obsession. It's impossible for an individual to withstand a targetted cyber attack so it seems pointless to go above and beyond to ultra encrypt every little thing
- jcranmer 7y agoIn modern practice, email is sent over TLS sockets already. Any good email client should prohibit you from using SMTP, POP, or IMAP with TLS, and for the past few years, even the MX-MX transfers in the backend have started to become protected (albeit mostly opportunistically at this point, I believe) with TLS. So the only people who can read email are you, your counterparty, your ESP, and your counterparty's ESP, assuming the email providers are following good practice.
- Godel_unicode 7y agoThis is an excellent explanation overall, I do however think that it's important to note that opportunistic STARTTLS is vulnerable to downgrade attacks by mitm. Since this would have to be a mitm of e.g. Gmail it's not trivial by any means, but neither is it completely out of reach (see for example the periodic rerouting of the internet caused by odd BGP advertisements). One further note is that you can know post-hoc if an email was delivered to Gmail via TLS by the presence or absence of a red lock in the Gmail app or web UI.
- bigiain 7y ago> STARTTLS is vulnerable to downgrade attacks by mitm. Not only that, but intentionally downgrading STARTTLS commands has as times been the default configuration for some Cisco routing gear. (Buy me a beer one day and I might tell you about the time I charged one of Australia's big four banks about $70k to debug that in a router on their internal network that nobody there knew existed...)
- JasonFruit 7y agoYour point 1 especially speaks to me. Phone-based messaging in general isn't appropriate for the things I would most like to be kept private between me and a recipient, because those sorts of things can't be created on a phone. I've found PGP pretty good for making that happen, when I'm working with someone who a) uses PGP also and b) exercises some caution when using it. I haven't found an option that I can trust that will work for me.
- floatingatoll 7y ago3 is incorrect for encrypted email: you cannot email someone unaware without their consent and expect them to willingly and ably participate in decrypting.
- Sniffnoy 7y agoWhy not? I mean, that's what publicly listing your public key is for, right?
- floatingatoll 7y agoNope. I have at least three public never-expiring keys that I am unable revoke and that remain listed as valid because the keyservers don’t occasionally revalidate proof of ability to decrypt.
- gsich 7y ago>never-expiring keys While this is bad, the keyserver issue is still valid.
- Sniffnoy 7y agoOh, that's a good point. Heh, I have one of those, too, which even caused a problem once[0]. I wouldn't expect people to find it first, though, because I wouldn't expect people to go to a keyserver first; I'd expect them to find my key on one of the places I have it listed on the web. I've never tried blindly entering someone's email address into a keyserver and just hoping they have a key; I've only sent PGP-encrypted email to people who list their keys on the web. [0]How it caused a problem: I added an email address to my public key (or maybe it expired or something, I forget), and asked people to refresh their copy of my key. One person instead downloaded it entirely anew from a keyserver and got the old one. Oops. (Admittedly I didn't explicitly use the word "refresh".) Anyway yeah -- though this problem had happened to me, it hadn't ocurred to me that it might be common; maybe this is more of a problem than I thought...
- 7y ago
- deleted 7y ago[deleted]
- NoGravitas 7y agoI strongly agree with this; email is not instant messaging, and there is not yet any secure replacement for email. We need a modern design for a successor protocol to email, and no one is working on it because they prefer instant messaging (or think other people do).
- Natanael_L 7y agoI think we're more likely to "accidentally" end up there via E2EE document collaboration tools that are in development now. One day, a while after they become usable and common, people will just realize they've been sharing documents E2EE in place of sending email, and they'll be using it for basically everything that matters. It would be a proper restart and allow for significant improvements in usability and security and everything else.
- NoGravitas 7y agoCan you point me to examples of such tools?
- Natanael_L 7y agoStill under active development, nothing is really ready to use yet
- amki 7y agoGoogle has tried with Wave but failed. I don't think it can be done. Everything would have to support SMTP as a fallback for the lot of people that just don't care and thus couldn't actually improve.