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The PGP problem (2019)

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Re: The PGP problem (2019)

#81

Earlier quoted context omitted.

One of the premises of modern cryptographic engineering is security under a hostile setting: it shouldn’t matter to a chat protocol that a server is proprietary or a network is centralized if the design itself is provably end-to-end encrypted. The server could be run by Satan and it wouldn’t matter. (Centralization itself is a red herring. One may as well claim that PGP is centralized, given that there’s only one pro…

I have no clue how you reached the conclusion of calling it a red herring. It matters - because Satan can disconnect the centralized nodes.

It’s a red herring because systems that achieve end-to-end security do so regardless of whether the underlying hosts are centralized or not. A typical network adversary wants you to downgrade the security properties of your protocol in the presence of an unreliable network, so they can pull more metadata out of you.

Re: The PGP problem (2019)

#82
I tried to find something in the article that bothered me, but I don’t find it very convincing. Points like "someone can forward your email unencrypted after they decrypt it" are just... well, yeah - that can happen no matter what method you choose. It feels like GPG gets hate for reasons other than what’s actually mentioned, and I'm completely oblivious to what those reasons might be.

Re: The PGP problem (2019)

#83

Recently, this opinionated list of PGP alternatives went around: https://soatok.blog/2024/11/15/what-to-use-instead-of-pgp/ One use case I've not seen covered is sending blobs asynchronously with forward secrecy. Wormhole requires synchronously communicating the password somehow, and Signal requires reasonable buy-in by the recipient. Basically, I'd like to just email sensitive banking and customer data in an encrypt…

One of the projects I alluded to in that post makes a technological solution to what you want easy to build, but the harder problem to solve is societal (i.e., getting it adopted).

https://github.com/fedi-e2ee/public-key-directory-specificat...

My current project aims to bring Key Transparency to the Fediverse for building E2EE on ActivityPub so you can have DMs that are private even against instance moderators.

One of the things I added to this design was the idea of "Auxiliary Data" which would be included in the transparency log. Each AuxData has a type identifier (e.g. "ssh-v2", "age-v1", "minisign-v0", but on the client-side, you can have friendly aliases like just "ssh" or "age"). The type identifier tells the server (and other clients) which "extension" to use to validate that the data is valid. (This is to minimize the risk of abuse.)

As this project matures, it will be increasingly easy to do this:

  // @var pkdClient -- A thin client-side library that queries the Public Key Directory
  // @var age -- An implementation of age
  async function forwardSecureEncrypt(file, identity) {
    const agePKs = await pkdClient.FetchAuxData(identity, "age");
    if (agePKs.length === 0) {
      throw new Error("No age public keys found");
    }
    return age.Encrypt(file, agePKs[0]);
  }
And then you can send the encrypted file in an email without a meaningful subject line and you'll have met your stated requirements.

(The degree of "forward secure" here depends on how often your recipient adds a new age key and revokes their old one. Revocation is also published through the transparency log.)

However, email encryption is such a mess that most people don't quite appreciate, so I'm blogging about that right now. :)

Also, Filippo just created a transparency-based keyserver for age, fwiw: https://words.filippo.io/keyserver-tlog/

Re: The PGP problem (2019)

#84

I feel like I'm taking pills, but hear me out. If there's one thing we learned from the Snowden leaks is that the NSA can't break GPG. Look at it from the POV of someone who like me isn't an expert: on the one hand I have ivory tower researchers telling me that GPG is "bad". On the other hand I have fact that the most advanced intelligence in the world can't break it. My personal conclusion is that GPG is actually fu…

The NSA can't break GPG assuming everything is working properly. This blog post (which to be fair I only skimmed) explains that GPG is a mess which could lead to things not working properly, and also gives real life examples. You may also want to see https://gpg.fail (you can tell they're from the ivory tower by the cat ears). The blog post also mentions bad UX, which you and I can directly appreciate (if anything I might expect ivory tower types to dismiss UX issues).

Re: The PGP problem (2019)

#85
post #47

Earlier quoted context omitted.

The tangent explicitly talks about generic messaging services. Whatsapp and Signal have more money than gpg. Thinking about it more, it is not even a tangent, because TFA says: "Use Signal. Or Wire, or WhatsApp, or some other Signal-protocol-based secure messenger."

I wrote TFA. Signal is a nonprofit. The article says to use Signal-protocol-based messengers, of which there are several. Your objection about money doesn't make sense.

Looking at the revenues and the salaries, nonprofit doesn't mean much these days.

Re: The PGP problem (2019)

#86
post #28

Earlier quoted context omitted.

https://en.wikipedia.org/wiki/Cryptocat#Reception_and_usage "In June 2013, Cryptocat was used by journalist Glenn Greenwald while in Hong Kong to meet NSA whistleblower Edward Snowden for the first time, after other encryption software failed to work." So it was used when Snowden was already on the run, other software failed and the communication did not have to be confidential for the long term. It would also be an…

Huh? There's no money in anything we're talking about here.

No money in anything?

Signal was made by people who then used it to push their get-rich-quick cryptocurrency scheme on users and who threw all their promises of being open-source and reproducible over board for it. The Signal people are absolutely not trustworthy for reasons of money and greed.

Re: The PGP problem (2019)

#87
post #28

Earlier quoted context omitted.

Huh? There's no money in anything we're talking about here.

No money in anything? Signal was made by people who then used it to push their get-rich-quick cryptocurrency scheme on users and who threw all their promises of being open-source and reproducible over board for it. The Signal people are absolutely not trustworthy for reasons of money and greed.

> Signal was made by people who then used it to push their get-rich-quick cryptocurrency scheme on users and who threw all their promises of being open-source and reproducible over board for it.

I reviewed Signal's cryptography last year over a long weekend: https://soatok.blog/2025/02/18/reviewing-the-cryptography-us...

There's a lot to be said for the utility of reverse engineering tools and skills, but I did not need them, because it was open source. Because Signal's client software still is open source.

Whatever you think about MobileCoin, it doesn't actually intersect with the message encryption features at all. At all.

The only part in Signal that's not entirely open source are the anti-spam features baked into the Signal Server software.

And, frankly, the security of end-to-end encryption messaging apps has so little to do with whatever the server software is doing that it's frankly silly to consider that relevant to these discussions. https://soatok.blog/2025/07/09/jurisdiction-is-nearly-irrele...

And, yes, this is only a server-side feature. See spam-filter (a git submodule) in https://github.com/signalapp/Signal-Server but absent from https://github.com/signalapp/Signal-Android or https://github.com/signalapp/Signal-iOS

> The Signal people are absolutely not trustworthy for reasons of money and greed.

I don't think you've raised sufficient justification for this point.

Re: The PGP problem (2019)

#88

I feel like I'm taking pills, but hear me out. If there's one thing we learned from the Snowden leaks is that the NSA can't break GPG. Look at it from the POV of someone who like me isn't an expert: on the one hand I have ivory tower researchers telling me that GPG is "bad". On the other hand I have fact that the most advanced intelligence in the world can't break it. My personal conclusion is that GPG is actually fu…

My impression is that GPG when used correctly is secure. But there are so many problems with it that the chances of shooting yourself with one of the footguns is too high for it to be a reliable solution.

The alternatives support newer encryption methods but nothing has fundamentally changed that doesn't make them less secure, but they have less footguns to worry about.

The weakest link in cryptography is always people.

Re: The PGP problem (2019)

#89

Anyone know why GitHub doesn't support signing commits with signify/minisign?

GitHub is not git and does not control what features get added to git.

It looks like there are some wrapper scripts to make git sign commits with other tools using the GPG cli interface but nothing official.

Re: The PGP problem (2019)

#90
post #78
post #71

This OpenPGP and GnuPG criticism is brought up regularly here, but the proposed alternatives come with their own downsides: some of those are proprietary, some are centralized systems or depend on such. In addition to all the inconvenience, when such centralized systems are blocked, casual users switch to explicitly backdoored options. The advertised IMs are tied to phone numbers, introducing both privacy and availab…

What is your issue with Sequoia PGP? It is not proprietary, it is not centralized and it is much better than GunPG from what I can tell.

I have no issues with it, and actually happy to see alternative implementations. Possibly because I did not use it much, but it does look fine to me. Not as a complete GPG replacement yet, since some software still depends on GPG, but a viable one, and a suitable one for most of the manual CLI usage (ignoring that its version on slightly older systems has a different interface, adding a bit of confusion; hopefully it is stable now). It was not listed among suggested alternatives in the linked article though, and from what I gather, the author would not be happy with it, either.
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