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Switching from GPG to Age

luke.hsiao.dev

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Re: Switching from GPG to Age

#61

Post by tux1968 »

lrvick wrote: post #52
somat wrote: post #50

Earlier quoted context omitted.

So just out of curiosity, what is this modern tooling? It was brought up previously in this thread without naming any names.

Just to name a few of the projects I work on, use, or find most interesting: https://keyoxide.org/ https://git.distrust.co/public/keyfork https://git.distrust.co/public/airgap https://codeberg.org/heiko/openpgp-pkcs11 https://codeberg.org/openpgp-card/openpgp-card-tools https://sequoia-pgp.org/ https://github.com/rpgp/rpgp https://www.nitrokey.com/news/2021/new-nitrokey-3-nfc-usb-c-... https://doc.qubes-os.org/en/lat…

It's hard to know how these pieces fit together, especially if you have a fuzzy mental-model of the objectives and potential benefits. Is there a gentle introduction you'd recommend?

Re: Switching from GPG to Age

#62

Post by tptacek »

lrvick wrote: post #35
fsmv wrote: post #34

Earlier quoted context omitted.

That's the whole point of age. That pgp is too complex and overloaded with features. By focusing on encryption only he can really get it right.

Even if you ONLY care about encrypting files presumably you want to be able to decrypt them far into the future, with confidence no one else can do so. If that is the case, you probably want: 1. a long lived keychain 2. a way to securely load private keys into smartcards such that they cannot be stolen by malware 3. a strategy to recover lost keys 4. a strategy to migrate from one keychain to another one 5. a way to…

age has Yubikey support. The idea that the PGP ecosystem "has you covered" on all these points is a bold claim. Certainly people talk about all these things, but when that system is put to the test, it rarely holds up. See for instance the keyserver fiasco.

Re: Switching from GPG to Age

#63

Post by zaphar »

lrvick wrote: post #15
zaphar wrote: post #3

Earlier quoted context omitted.

Literally the only thing I ever actually used gpg for was file encryption. I tried dong key management and signatures for a very brief period 20 years ago and gave up because no one else was doing it and it was annoying trying to do the right opsec things with no payoff. Ever since then, as far as I can tell there has been a very small very niche group who use gpg for anything other than file encryption. So age is th…

By very small niche group, you mean every maintainer of every widely used production linux distribution and most of the core packages that form the supply train trust layer for the entire internet? Or every reasonably competent security vulnerability disclosure team? (Even Google and Apple!) PGP is the only standardized cryptographic online identity layer we have and still very heavily used by anyone working on secur…

Yes. That they have a large impact does not change the fact that not I nor anyone in my close circle uses it for that. It has been relegated to a specialized domain and use case. I have no use for maintaining a signing key. All the communications I need to secure and verify identity use a different technology for it. The fact that some tools I run might use it in the background is entirely abstracted away for me and they could get swapped by something else without me once noticing.

My point still stands.

Re: Switching from GPG to Age

#64

Post by tptacek »

johnisgood wrote: post #44
Vegenoid wrote: post #36

Earlier quoted context omitted.

I think I'm missing something, how does asking for their public key improve security or verify their identity?

Asking for their public key lets you encrypt messages that only their private key can decrypt, and verify signatures they create. It doesn't by itself prove their real identity, you still need to verify the key's authenticity (e.g. via fingerprint comparison or a trusted keyserver) to avoid impersonation or man-in-the-middle attacks.

He's asking how this procedure learns which public keys are trustworthy, not how asymmetric cryptography works.

Re: Switching from GPG to Age

#65

Post by Avamander »

johnisgood wrote: post #8
Avamander wrote: post #6

Earlier quoted context omitted.

> Not only can it do all the ssh-agent operations It can not. Doesn't work with PKCS#11 PIV. In general GPG's behavior with SmartCards is idiotic and interferes with many other applications. It's good that people don't use GPG more often and I can just purge it from my systems.

What do you mean? I use GPG with SSH (or SSH with GPG) all the time, and I need gpg-agent for that. GPG's agent replaces ssh-agent and serves SSH keys derived from your GPG key. Can you do this with Age? If not, then I am going to stick to GPG.

I'm unsure what was unclear. It simply does not provide PIV support and it interferes with other software that wants to utilise SmartCards.

Can Age interfere with all SmartCard usage? No clue.

Re: Switching from GPG to Age

#66

Post by akerl_ »

rmunn wrote: post #45
Vegenoid wrote: post #36

Earlier quoted context omitted.

I think I'm missing something, how does asking for their public key improve security or verify their identity?

As for how it improves security, I'm going to hazard a guess that many of the people sending zikduruqe those messages hadn't previously set up a PGP key. So by asking for the public key and refusing to send them the credentials until he receives it, he's forcing them to set one up, which then makes it possible for them to do things like sign messages. Just making someone set up a keypair doesn't mean they'll use it c…

It’s so easy to use insecurely that I will argue that employees setting up PGP keys and then potentially trying to use them does weaken the company’s security posture.

Re: Switching from GPG to Age

#67

Post by akerl_ »

rmunn wrote: post #43
Vegenoid wrote: post #36

Earlier quoted context omitted.

I think I'm missing something, how does asking for their public key improve security or verify their identity?

It allows the security guy (in this case, zikduruqe) to send an email that can only be read by the person who possesses the corresponding private key. Which means that either the email is going to the executive who really does own the account, or else that the attacker has already breached that executive's laptop to the point of having acquired his private key (and passphrase, if there was one), in which case phishin…

So I email you asking for something. You say “send me your public key first”.

I generate a key pair and send the public key to you. You encrypt response giving me what I wanted.

How do you have any idea that I’m the person I said I am?

Re: Switching from GPG to Age

#68

Post by Vegenoid »

tptacek wrote: post #64
johnisgood wrote: post #44

Earlier quoted context omitted.

Asking for their public key lets you encrypt messages that only their private key can decrypt, and verify signatures they create. It doesn't by itself prove their real identity, you still need to verify the key's authenticity (e.g. via fingerprint comparison or a trusted keyserver) to avoid impersonation or man-in-the-middle attacks.

He's asking how this procedure learns which public keys are trustworthy, not how asymmetric cryptography works.

I think what I’ve gathered is that the person I replied to is going with a TOFU model of key security (trust on first use), or is just seeking to avoid plaintext passwords in slack messages and is treating the key as disposable for the one-time encryption of the password.

Presumably they must trust that the user messaging them on slack is indeed who they say they are and is in control of the account.

If I’ve understood correctly, this seems like one of those cases where PGP is adding quite little security to the system, and may be preventing the implementation of more secure systems if it is providing a false sense of security.

But it’s probably just someone doing their best in a system beyond their control.

Re: Switching from GPG to Age

#69

Post by lrvick »

tptacek wrote: post #59
lrvick wrote: post #56

Earlier quoted context omitted.

Citation needed. Both Apple and Google have updated these pages with security disclosure PGP keys in the last year. https://support.apple.com/en-us/101985 https://about.google/company-info/appsecurity/ I design most corporate bug bounty programs the same way. Sure, people rarely use PGP, but the ones that do are usually serious and high quality, and we let them skip the tier 1 queue. Script kiddies never know how to…

It has not at all been my experience that PGP-encrypted bounty submissions are fast-tracked and most (almost all, in fact) good bounty submissions aren't encrypted. Google downplays PGP in the link you provided. Apple doesn't ask people to use theirs.

Are we looking at the same links?

It is provided as an option, the ONLY option, for those that feel encryption is merited for a sensitive report.

Google page: "If you feel the need, please use our PGP public key to encrypt your communications with us."

Apple page: "Apple security advisories are signed with the Apple Product Security PGP key. Sensitive security information may be encrypted to this key when communicating with Apple Product Security."

Re: Switching from GPG to Age

#70

Post by lrvick »

tptacek wrote: post #62
lrvick wrote: post #35

Earlier quoted context omitted.

Even if you ONLY care about encrypting files presumably you want to be able to decrypt them far into the future, with confidence no one else can do so. If that is the case, you probably want: 1. a long lived keychain 2. a way to securely load private keys into smartcards such that they cannot be stolen by malware 3. a strategy to recover lost keys 4. a strategy to migrate from one keychain to another one 5. a way to…

age has Yubikey support. The idea that the PGP ecosystem "has you covered" on all these points is a bold claim. Certainly people talk about all these things, but when that system is put to the test, it rarely holds up. See for instance the keyserver fiasco.

Barely. Age has Yubikey support with no reasonable long term key discovery, backup, or rotation strategy as far as I can tell. All things modern PGP tooling supports.

But this is what happens when people try to re-invent the wheel without thinking through all the problems the original solution solved.

Also I do put these systems to the test, regularly, and rest billions of dollars of infrastructure on them.

Anyone is free to hit up my team in our public channels with any PGP gotchas. Happy to help.

It is easy to point at past black eyes of any technology, but I stand by PGP for the use cases we recommend it for today as the least bad option for those use cases.

Also, Hagrid keyservers (openpgp.org) do email verification now and are a new generation of keysever built from scratch. The legacy ones are a mess and can be ignored.

Today though, Web Key Discovery, PGP DNS records,and Keyoxide are much better ways to discover and distribute keys and signatures now.

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