5 ms·

I think it already has. Maybe not the underlying tech, but certainly for encrypt emails. But I think the outcome of this is not "something fresh" but rather "g

by berkes 3y ago

I think it already has. Maybe not the underlying tech, but certainly for encrypt emails. But I think the outcome of this is not "something fresh" but rather "giving up on the idea of encrypted emails altogether". We have far superior communication channels that are secure, easy and private today (Signal, Matrix, WhatsApp, iMessage); That problem is solved. Storing emails secure and encrypted is solved too, by providers such as protonmail, fastmail, tutanota and many others. So what does GPG/PGP really solve still? The one use-case that I strongly see it shine, is where mail-notifications are signed. I've only ever seen Kraken do this: Upload my GPG/PGP pub key in their web-interface, and have them sign and encrypt mails to me with that. It very much solves phishing and MITM on email-notifications (and password reset mails and such). Comes with two serious problems though: the UX on my client-end still sucks; e.g. I never managed to set-up PGP on my android client, so I cannot read their mails from my phone. "subject: Login attempt from X" body: garbled. And generation and rotation of the keys is as frustrating as ever. It certainly is not a feature for "my mom".

ISV_Damocles 3y ago
I think we agree[0] on this. Email encryption isn't ever going to be a thing because of the way email itself works. But email signing would help a lot. I still don't think GPG does this very well, though, because of issues with key rotation/invalidation/etc. [0]: https://news.ycombinator.com/item?id=38557771 https://news.ycombinator.com/item?id=38557771
- arp242 3y ago
  I wish it would just use TOFU ("trust on first use") by default. It's not 100% fool-proof, but actually does cover a large number of use-cases, and is certainly better than nothing. UI: "billing@paypal.com: we never seen this sender before, be careful" "billing@paypal.com: this is verified to be the same sender" "billing@paypal.com: ACHTUNG! THIS IS SOMEONE ELSE" You can of course still manually add keys, and you can even do automatic or semi-automatic key rotation with some new header (e.g. "X-New-Key: [...]" that's signed with the old).
  - woodruffw 3y ago
    > You can of course still manually add keys, and you can even do automatic or semi-automatic key rotation with some new header (e.g. "X-New-Key: [...]" that's signed with the old). Headers aren't part of an encrypted or authenticated body, so this is trivial to perform a key replacement attack against.
    - arp242 3y ago
      Or MIME part, or change the spec to include some headers (I thought it did?) – that's not an important detail here.
    - mschuster91 3y ago
      > Headers aren't part of an encrypted or authenticated body, so this is trivial to perform a key replacement attack against. DKIM can be leveraged for that, although DKIM is one hell of a gun to give someone to shoot themselves.
    - morelisp 3y ago
      DNS records aren't part of the encrypted or authenticated channel, so SSH is trivial to perform a key replacement attack against?
      - woodruffw 3y ago
        Sorry, is this a rhetorical question? I thought the fact that SSH does TOFU was (somewhat) common knowledge, which is why it spits out all kinds of scary MITM warnings when a host fingerprint changes. If you're connecting to an SSH server for the first time and don't already have a pre-established host fingerprint, then yes: someone who controls your server's DNS records can redirect you to another SSH host, which you'll then (presumably) enter your password into.
        deleted 3y ago
        [deleted]
        3y ago
ekTHEN 3y ago
I'm using FairEmail [0] as a client on Android which supports PGP and i am quite happy with it. [0] https://email.faircode.eu/ https://email.faircode.eu/
d0mine 3y ago
Is it a coincidence that the tech you mentioned includes CIA honeypots e.g., protonmail? gnupg looks like something that actually can keep your secrets (at rest, otherwise a less-likely-to-backdoored convenient option is Telegram).
- esafak 3y ago
  Are you sure? Please share your evidence. https://www.reddit.com/r/ProtonMail/comments/14demhj/debunking_proton_and_ciansa_fake_news/ https://www.reddit.com/r/ProtonMail/comments/14demhj/debunki...
  - uselpa 3y ago
    A random Reddit post is hardly evidence. My personal opinion is that they sell snake oil (a.k.a. secure email).
  - d0mine 3y ago
    when you are dealing with the trillion dollar war propaganda machine any link one might provide will be drown out by noise "debunking" it. Do your own research. I found the initial links on hacker news.
    - esafak 3y ago
      What links?
- Valodim 3y ago
  I'm not sure what you were trying to say here about telegram, but they are completely unencrypted, for nearly all intents and purposes messages are stored in plaintext on the server. They just succeeded impressively in twisting that fact away via marketing.
  - d0mine 3y ago
    It has been discussed to death already. There is e2e encryption if you need it. "completely unencrypted" is just false.
thayne 3y ago
> (Signal, Matrix, WhatsApp, iMessage); None of which are anywhere close to as ubiquitous as email. None of which are well suited to long messages. Only one of those (matrix) is federated. Only one (matrix) wasn't designed specifically for use on mobile devices. Yes, the others can be used on a desktop, but the experience isn't great.
- tptacek 3y ago
  Hold on, there's a sleight of hand here. You're trying to compare all of email against WhatsApp. Now, it's possible that if you took transactional email out of the picture, and just stuck with interpersonal communication, WhatsApp could beat email. But that doesn't matter, because in this discussion, the figure of merit is encrypted email, and on that metric, every single one of those platforms on their own roflstomps email for daily usage.
  - viccuad 3y ago
    Only Matrix is federated, like email. I really enjoy sending emails without opening an account for each recipient or being subservient to 1 stack provider for 50 years, with all the inbreeding that entails.
    - tptacek 3y ago
      That wasn't the point being made, was it?
  - thayne 3y ago
    > Now, it's possible that if you took transactional email out of the picture, and just stuck with interpersonal communication, WhatsApp could beat email Everyone I know uses email. No one I know uses whatsapp. A couple of people I know use Signal. A handful use iMessage. > But that doesn't matter, because in this discussion, the figure of merit is encrypted email, Ok, let's consider one case where encrypted email is commonly used: reporting security vulnerabilities. Do you really think any of these would be a good medium for that? Do you see companies or other organizations putting a whatsapp username as the contact in their security.txt? I do want there to be a more secure replacement for email. But most of the newer e2ee messaging systems can't really fully replace email.
0xDEAFBEAD 3y ago
>We have far superior communication channels that are secure, easy and private today (Signal, Matrix, WhatsApp, iMessage) These are valuable tools, but they aren't usable on the command line the way gpg is. Signal doesn't help me sign an update to my software package. Also I think the web of trust is a pretty cool concept, in theory at least. I don't know if anything outside GPG supports it.

by berkes 3y ago

ISV_Damocles 3y ago

I think we agree[0] on this. Email encryption isn't ever going to be a thing because of the way email itself works. But email signing would help a lot. I still don't think GPG does this very well, though, because of issues with key rotation/invalidation/etc. [0]: https://news.ycombinator.com/item?id=38557771 https://news.ycombinator.com/item?id=38557771

arp242 3y ago
I wish it would just use TOFU ("trust on first use") by default. It's not 100% fool-proof, but actually does cover a large number of use-cases, and is certainly better than nothing. UI: "billing@paypal.com: we never seen this sender before, be careful" "billing@paypal.com: this is verified to be the same sender" "billing@paypal.com: ACHTUNG! THIS IS SOMEONE ELSE" You can of course still manually add keys, and you can even do automatic or semi-automatic key rotation with some new header (e.g. "X-New-Key: [...]" that's signed with the old).
- woodruffw 3y ago
  > You can of course still manually add keys, and you can even do automatic or semi-automatic key rotation with some new header (e.g. "X-New-Key: [...]" that's signed with the old). Headers aren't part of an encrypted or authenticated body, so this is trivial to perform a key replacement attack against.
  - arp242 3y ago
    Or MIME part, or change the spec to include some headers (I thought it did?) – that's not an important detail here.
  - mschuster91 3y ago
    > Headers aren't part of an encrypted or authenticated body, so this is trivial to perform a key replacement attack against. DKIM can be leveraged for that, although DKIM is one hell of a gun to give someone to shoot themselves.
  - morelisp 3y ago
    DNS records aren't part of the encrypted or authenticated channel, so SSH is trivial to perform a key replacement attack against?
    - woodruffw 3y ago
      Sorry, is this a rhetorical question? I thought the fact that SSH does TOFU was (somewhat) common knowledge, which is why it spits out all kinds of scary MITM warnings when a host fingerprint changes. If you're connecting to an SSH server for the first time and don't already have a pre-established host fingerprint, then yes: someone who controls your server's DNS records can redirect you to another SSH host, which you'll then (presumably) enter your password into.
      - deleted 3y ago
        [deleted]
      - 3y ago

ekTHEN 3y ago

I'm using FairEmail [0] as a client on Android which supports PGP and i am quite happy with it. [0] https://email.faircode.eu/ https://email.faircode.eu/

d0mine 3y ago

Is it a coincidence that the tech you mentioned includes CIA honeypots e.g., protonmail? gnupg looks like something that actually can keep your secrets (at rest, otherwise a less-likely-to-backdoored convenient option is Telegram).

esafak 3y ago
Are you sure? Please share your evidence. https://www.reddit.com/r/ProtonMail/comments/14demhj/debunking_proton_and_ciansa_fake_news/ https://www.reddit.com/r/ProtonMail/comments/14demhj/debunki...
- uselpa 3y ago
  A random Reddit post is hardly evidence. My personal opinion is that they sell snake oil (a.k.a. secure email).
- d0mine 3y ago
  when you are dealing with the trillion dollar war propaganda machine any link one might provide will be drown out by noise "debunking" it. Do your own research. I found the initial links on hacker news.
  - esafak 3y ago
    What links?
Valodim 3y ago
I'm not sure what you were trying to say here about telegram, but they are completely unencrypted, for nearly all intents and purposes messages are stored in plaintext on the server. They just succeeded impressively in twisting that fact away via marketing.
- d0mine 3y ago
  It has been discussed to death already. There is e2e encryption if you need it. "completely unencrypted" is just false.

thayne 3y ago

> (Signal, Matrix, WhatsApp, iMessage); None of which are anywhere close to as ubiquitous as email. None of which are well suited to long messages. Only one of those (matrix) is federated. Only one (matrix) wasn't designed specifically for use on mobile devices. Yes, the others can be used on a desktop, but the experience isn't great.

tptacek 3y ago
Hold on, there's a sleight of hand here. You're trying to compare all of email against WhatsApp. Now, it's possible that if you took transactional email out of the picture, and just stuck with interpersonal communication, WhatsApp could beat email. But that doesn't matter, because in this discussion, the figure of merit is encrypted email, and on that metric, every single one of those platforms on their own roflstomps email for daily usage.
- viccuad 3y ago
  Only Matrix is federated, like email. I really enjoy sending emails without opening an account for each recipient or being subservient to 1 stack provider for 50 years, with all the inbreeding that entails.
  - tptacek 3y ago
    That wasn't the point being made, was it?
- thayne 3y ago
  > Now, it's possible that if you took transactional email out of the picture, and just stuck with interpersonal communication, WhatsApp could beat email Everyone I know uses email. No one I know uses whatsapp. A couple of people I know use Signal. A handful use iMessage. > But that doesn't matter, because in this discussion, the figure of merit is encrypted email, Ok, let's consider one case where encrypted email is commonly used: reporting security vulnerabilities. Do you really think any of these would be a good medium for that? Do you see companies or other organizations putting a whatsapp username as the contact in their security.txt? I do want there to be a more secure replacement for email. But most of the newer e2ee messaging systems can't really fully replace email.

0xDEAFBEAD 3y ago

>We have far superior communication channels that are secure, easy and private today (Signal, Matrix, WhatsApp, iMessage) These are valuable tools, but they aren't usable on the command line the way gpg is. Signal doesn't help me sign an update to my software package. Also I think the web of trust is a pretty cool concept, in theory at least. I don't know if anything outside GPG supports it.