🔐 Every unencrypted email is readable by 10+ entities and stored forever.

[blort@social.tchncs.de]

@nicfab

@yunohost
@nextcloud (Mail)
@freedomboxfndn

Are / will you support this option for encrypted email? (^^^ Previous toot)

#Encryption #Email #WKD #Privacy #Yunohost #Nextcloud #Freedombox #WebKeyDirectory #Cryptography #OpenPGP

[nicfab@fosstodon.org]

@Blort @yunohost @nextcloud @freedomboxfndn
Yes, of course! Why not?
I have my WKD

[blort@social.tchncs.de]

@nicfab

FYI That question was primarily aimed at Yunohost / Nextcloud / Freedombox, as I'd love to know if the tools I already use, make this user friendly to setup yet. ;)

Either way, this looks fascinating! While I lack the technical expertise to validate the approach, the promise is extremely appealing, raising the possibility that the most popular, #FOSS social network on the planet (email) could finally be made encrypted for the masses (such as I), doing for email what Let's Encrypt did for web servers.

Coming more from a marketing background myself, my first thought was what it would take to get widespread adoption, which seems to be support from major (FOSS + commercial) email server applications. From a quick skim of your article, it seems adding support shouldn't be onerous...

[nicfab@fosstodon.org]

@Blort
Sorry for the misunderstanding.
I strongly believe that everyone should communicate exclusively via encrypted email, and I have held this position for many years.
I published several posts on my blog on that topic.

[chimbosonic@fosstodon.org]

@nicfab seeing https://wkd.dp42.dev referenced has made my day!

[blort@social.tchncs.de]

@nicfab I take full credit / blame for any misunderstanding there! I forgot Masto would automatically @ you in any reply, and didn't think about how it would look like I was directing the question at you. My bad!

I'd love to see a wider discussion of this though, as the ramifications could be groundbreaking to private communications.

If there's one thing my professional life has taught me, it's how making things even a tiny bit easier / harder can have huge ramifications on what people actually do (or not).

This seems like it could genuinely make encrypted email easy after decades of adoption being very hard. That gets me very interested in the strengths and limitations of the approach and how it's adoption could be encouraged.

Could it be extended to something like @delta chat?

[nicfab@fosstodon.org]

@chimbosonic I mentioned your tool in my article. Read it! 😀
Congratulations on your work! Great resource!

[delta@chaos.social]

@Blort @nicfab we know about wkd and some of us have engaged with it in earlier times. Our current trajectory of #chatmail developments is not directly fitting as we are aiming to hide all cryptographic identity information from the transport layer (email servers). Wkd rather reinforces the central role of email servers in managing and controlling a users cryptographic identity. Besides there are error cases (wkd down/erroring), stale keys and other issues that cause UX challenges.

[pierricd@mastodon.green]

@nicfab I did not know of this, and find it fascinating. I use proton with a custom domain, so I don't benefit from it based on the article. Next project: setting up my wkd server!

Only downside: I make extensive use of catch-all addresses, and I suppose wkd doesn't account for a "default user inbox" if it relies on username hashes like the article explains. But still worth setting up!

[nicfab@fosstodon.org]

@delta @Blort I won't go into technical details here. There is an IETF draft that I referred to. I appreciate your work, but standards must be respected. If any WKDs are not working, there may be misconfiguration issues.

[nicfab@fosstodon.org]

@PierricD You can set up WKD with your domain name even if the MX records are on Proton. You need a server.

[delta@chaos.social]

@nicfab @Blort we know there is an IETF doc about wkd. Delta is probably one of the most standards based messengers out there https://github.com/chatmail/core/blob/main/standards.md
But that doesn't mean any IETF standard is unconditionally a good idea for resilient decentralized messaging.

[tudobem@social.tchncs.de]

@nicfab @PierricD what would the average annual server cost be if one were to set up a server simply for WKD? I‘m not a tech guy unfortunately, so I find it difficult to assess

[lennybacon@infosec.exchange]

@nicfab I appreciate every attempt to make the web more secure by default.

What is your opinion on if I would state: Isn’t encrypted mail also stored forever and readable in the future? As e-mail lacks PFS…

I’m more concerned about that and things like headers being not encrypted and therefore, leaking meta data, than getting my keys to ppl.

If things must change it is probably SMTP that needs a successor with things like double ratchet session keys and key exchange parameters. And while we’re on it, probably some post quantum ability would fit the timeline we are in.

What do you think?

[micha@23.social]

@nicfab @koehntopp Sounds too good. Hope it's not. 😃👍

[nicfab@fosstodon.org]

@micha @koehntopp Why not?

[thedarktangent@defcon.social]

@nicfab @yawnbox An article about email security, but no mention of S/MIME?

[nicfab@fosstodon.org]

@lennybacon 1/6
Your analysis hits the nail on the head. The fundamental architecture of email predates modern cryptography, and what we do today is essentially retrofitting security onto a protocol from the 1970s.

[nicfab@fosstodon.org]

@lennybacon 2/6
The lack of PFS is indeed critical: every encrypted email becomes a time capsule waiting for quantum computers or a key compromise. Unlike Signal or Matrix, which utilize double-ratchet algorithms to ensure both forward and backward secrecy, email encryption remains static — a single key leak compromises entire email histories.

[nicfab@fosstodon.org]

@lennybacon 3/6
And metadata exacerbates the issue: even with PGP/S/MIME, headers expose communication patterns, timestamps, and relationships that can be more revealing than the message content itself. WKD is pragmatic incrementalism: it solves the decades-old “chicken and egg” of key distribution, but it’s still polishing brass on the Titanic. Real progress requires a protocol redesign.