The lack of any higher level crypto primitives in the Swift standard library seems to have resulted in people just deciding to shell out to openssl to generate a CSR, which feels like an important lesson
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This feels like not *necessarily* the wrong implementation but I’d prefer the library that shells out to OpenSSL to be part of the Swift standard library
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Involving unnecessary CLI interfaces and parsing in both directions is far worse than using it directly. It can be used in a separate process (which does not imply any isolation without further work) without involving the CLI interface if that was actually the goal.
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I'm thinking about GPG and Git here as examples, although Git was specifically designed to operate this way and maybe GPG is not a great model for anything security-related
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there was efail.de where some of the vulns were due to integrity errors from shelling out to GPG not being propagated to the MUAs, which is one of the risks of shelling out
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This makes me want to get started again on my Go GPG library interfaces again, but I know I’ll forget about it until the next time.
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Use modern, secure cryptography instead. Secure messaging should be done with proper secure messaging protocols. Standalone authenticated file encryption should be done with github.com/FiloSottile/age. File signing should be done with signify/minisign which have libraries available.
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I’m definitely down with using something more modern and applicable, but (aside from atrocious usability issues) I have trouble understanding what’s so fatally flawed about PGP as a de facto standard.
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And the problems with the other ones are lack of widespread support in mail/file/desktop clients compared to PGP, which is a fixable problem, but we gotta settle on a smaller subset of things before that’ll happen.
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Meanwhile, I still need to interact with PGP signed/encrypted files, so making a library that does that properly instead of shelling out to GPG is something that has potential benefit to me.
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PGP for secure messaging especially via email is very misguided. Even a decent implementation wouldn't have decent / expected security properties. A secure messaging system should have automatic rotation of long-lived keys, forward secrecy for sessions, proper verification, etc.
If you want federated, end-to-end encrypted messaging use Matrix instead of insecure cryptography poorly bolted onto a protocol ill suited for it. It doesn't solve the hard problems. Can't paper over the fact that it's fundamentally designed wrong with awful security properties.
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In general, I’m happy to concede that there’s not a great one-size-fits-all solution for what PGP tries to tackle, namely encryption/signing of files at rest (for multiple recipients) and encryption/signing of ephemeral/ish messages in transit, which is more session-oriented.
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