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  • David Chisnall (*Now with 50% more sarcasm!*)david_chisnall@infosec.exchange
    Oct 30, 2026, 11:34 AM

    I first encountered Proton because they were claiming to be a 'secure' email service but didn't really list a threat model and... they're email. There's basically no way of making email secure against a realistic modern threat model. You can do S/MIME or PGP and get end-to-end encryption, but they're so painful to use that the odds are that (unless all of your friends are masochist crypto nerds), no one you correspond with will be using either. I couldn't even get my solicitor to use S/MIME for signing emails to give some integrity guarantees, let alone confidentiality. And, if you do this, email still puts all of the headers in plain text so the provider can see them and has access to the entire shape of the connection graph. So they felt like snake oil and I largely ignored them.

    The next time I heard about them was when they funded a far-right YouTuber and endorsed Trump. So they seemed like people who probably weren't to be trusted with any data.

    And now they're apparently all in on AI and firing people who say things like 'maybe we should do thirty seconds of security review before we push the output of the bullshit generator to production?'

    My surprise level is sitting at approximately 0%.

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Replies

  • r-holdrhold@norden.social
    Oct 30, 2026, 11:42 AM

    @david_chisnall The far-right sorry reached me just in time to avoid them.

    I think their main selling point is being relatively easy to use and convenient.

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  • David Chisnall (*Now with 50% more sarcasm!*)david_chisnall@infosec.exchange
    Oct 30, 2026, 3:20 PM

    @MikeStok @rhold

    I strongly disagree. I'm not sure if he was quoting, but Ross Anderson liked to say that security without usability is not security. Security design is about making sure that the easiest way of doing a thing is secure. Anything else is liability shifting design, not security design.

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  • awoodlandawoodland@fosstodon.org
    Oct 30, 2026, 12:44 PM

    @david_chisnall it seems like a huge miscalculation for a company that sells paranoia and security as a business to entirely dismiss them as valid concerns internally.

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  • Cliff'sEsportCornerCliffsEsport@mastodon.social
    Oct 30, 2026, 1:23 PM

    @david_chisnall Yeah I looked into PGP for email, but I am like who would I even talk to that A) could use it B) would use proper OpSec for machine running it C) would want to use it. Like the grugq was only person I could think of, but couldn't think of anything I'd chat with him at my current skill level that would need it. Basically everyone uses gmail/apple/MS for email and almost all if not all are logged into browser(s) so it seemed like security theatre at best.

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  • David Chisnall (*Now with 50% more sarcasm!*)david_chisnall@infosec.exchange
    Oct 30, 2026, 1:38 PM

    @CliffsEsport

    FreeBSD required PGP-signed emails for things like having the mail admin team do things. They checked the PGP key against the key in the handbook. I ended up with this flow every time I wanted to send them an email:

    1. Generate a new key pair.
    2. Commit the new public to the handbook.
    3. Use the private key to sign the message.
    4. Send the message.
    5. Discard the key pair.

    The security of the PGP keys was therefore bounded by the security of my SSH key. At which point, we can remove email entirely from the attack surface and I can just give them access to a file on a shared server. I don't think they still use it (or, at least, don't require it).

    One of the free TLS certificate providers used to offer S/MIME certificates and that worked a bit better. Most mail clients support S/MIME. It would be nice if Let's Encrypt with DNS authentication would sign S/MIME certificates (or, ideally, sign certs that allowed signing S/MIME certs in a specific domain, though I'm not sure that's a thing the certificates can encode). Even then, there's a problem of what do you do in the case of failure? I had some people who used S/MIME with a cert that they wanted you to install separately outside of the PKI, but if you didn't then all emails from them just showed up as failed authentication. What do you do? It turns out: just trust them.

    Certificate revocation and rollover is also a while problem with S/MIME, you really need to do the checks as the email arrives because there's no guarantee that the certificate will still be valid when you get around to reading the message (or, especially, if you reread it a year later).

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  • Owen Lyncholynch@mathstodon.xyz
    Oct 30, 2026, 1:49 PM

    @david_chisnall gahhh I just moved to proton without knowing about this because I wanted to use a centralized, maintained sync server for passwords so that I don't shoot myself in the foot and lock myself out of things by being stupid (I was using syncthing with keepassx before, and it did *not* feel reliable). Do you have an alternative for managed password managers you recommend?

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  • John QMaitre@mastodon.online
    Oct 30, 2026, 3:08 PM

    @david_chisnall For a long time, I used a Thunderbird plugin and PGP-signed every email by default, with my pubkey attached. I thought that visibility might raise awareness of the ease of access to more secure email among my friends and colleagues.

    Sadly, I never saw any traction there, and yet the convenience has never regressed. I figure it _should_ be possible to interoperate with platforms like Proton / Tuta ... there is still a chance.

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  • Jimjimliu@mastodon.social
    Oct 30, 2026, 4:09 PM

    @david_chisnall When one realizes that Protonmail’s business model has always been ransomeware-enablement-as-a-service, it all starts to make sense. 🫠

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