OpenPGP key transition

1. blog

This is a short announcement to say that I have changed my main OpenPGP key. A signed statement is available with the cryptographic details but, in short, the reason is that I stopped using my old YubiKey NEO that I have worn on my keyring since 2015.

I now have a YubiKey 5 which supports ED25519 which features much shorter keys and faster decryption. It allowed me to move all my secret subkeys on the key (including encryption keys) while retaining reasonable performance.

I have written extensive documentation on how to do that OpenPGP key rotation and also YubiKey OpenPGP operations.

Warning on storing encryption keys on a YubiKey

People wishing to move their private encryption keys to such a security token should be very careful as there are special precautions to take for disaster recovery.

I am toying with the idea of writing an article specifically about disaster recovery for secrets and backups, dealing specifically with cases of death or disabilities.

Autocrypt changes

One nice change is the impact on Autocrypt headers, which are considerably shorter.

Before, the header didn't even fit on a single line in an email, it overflowed to five lines:

Autocrypt: addr=anarcat@torproject.org; prefer-encrypt=nopreference;
 keydata=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
 S60bWyLH4QnGxNaOoQvuAXiCYV4amKl7hSuDVZEn/9etDgm/UhGn2KS3yg0XFsqI7V/3RopHiDT+k7+zpAKd3st2V74w6ht+EFp2Gj0sNTBoCdbmIkRhiLyH9S4B+0Z5dUCUEopGIKKOSbQwyD5jILXEi7VTZhN0CrwIcCuqNo7OXI6e8gJd8McymqK4JrVoCipJbLzyOLxZMxGz8Ki0b9O844/DTzwcYcg9I1qogCsGmZfgVze2XtGxY+9zwSpeCLeef6QOPQ0uxsEYSfVgS+onCesSRCgwAPmppPiva+UlGuIMun87gPpQpV2fqFg/V8zBxRvs6YTGcfcQjfMoBHmZTGb+jk1//QAgnXMO7fGG38YH7iQSSzkmodrH2s27ZKgUTHVxpBL85ptftuRqbR7MzIKXZsKdA88kjIKKXwMmez9L1VbJkM4k+1Kzc5KdVydwi+ujpNegF6ZU8KDNFiN9TbDOlRxK5R+AjwdS8ZOIa4nci77KbNF9OZuO3l/FZwiKp8IFJ1nK7uiKUjmCukL0od/6X2rJtAzJmO5Co93ZVrd5r48oqUvjklzzsBNBFmeC3oBCADEV28RKzbv3dEbOocOsJQWr1R0EHUcbS270CrQZfb9VCZWkFlQ/1ypqFFQSjmmUGbNX2CG5mivVsW6Vgm7gg8HEnVCqzL02BPY4OmylskYMFI5Bra2wRNNQBgjg39L9XU4866q3BQzJp3r0fLRVH8gHM54Jf0FVmTyHotR/Xiw5YavNy2qaQXesqqUv8HBIha0rFblbuYI/cFwOtJ47gu0QmgrU0ytDjlnmDNx4rfsNylwTIHS0Oc7Pezp7MzLmZxnTM9b5VMprAXnQr4rewXCOUKBSto+j4rD5/77DzXw96bbueNruaupb2Iy2OHXNGkB0vKFD3xHsXE2x75NBovtABEBAAHCwqwEGAEIACAWIQSNyQHOZBRsBIrVD7t5IVJSe3WSHgUCWZ4LegIbAgFACRB5IV
 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

After the change, the entire key fits on a single line, neat!

Autocrypt: addr=anarcat@torproject.org; prefer-encrypt=nopreference;
 keydata=xjMEZHZPzhYJKwYBBAHaRw8BAQdAWdVzOFRW6FYVpeVaDo3sC4aJ2kUW4ukdEZ36UJLAHd7NKUFudG9pbmUgQmVhdXByw6kgPGFuYXJjYXRAdG9ycHJvamVjdC5vcmc+wpUEExYIAD4WIQS7ts1MmNdOE1inUqYCKTpvpOU0cwUCZHZgvwIbAwUJAeEzgAULCQgHAwUVCgkICwUWAgMBAAIeAQIXgAAKCRACKTpvpOU0c47SAPdEqfeHtFDx9UPhElZf7nSM69KyvPWXMocu9Kcu/sw1AQD5QkPzK5oxierims6/KUkIKDHdt8UcNp234V+UdD/ZB844BGR2UM4SCisGAQQBl1UBBQEBB0CYZha2IMY54WFXMG4S9/Smef54Pgon99LJ/hJ885p0ZAMBCAfCdwQYFggAIBYhBLu2zUyY104TWKdSpgIpOm+k5TRzBQJkdlDOAhsMAAoJEAIpOm+k5TRzBg0A+IbcsZhLx6FRIqBJCdfYMo7qovEo+vX0HZsUPRlq4HkBAIctCzmH3WyfOD/aUTeOF3tY+tIGUxxjQLGsNQZeGrQI

Note that I have implemented my own kind of ridiculous Autocrypt support for the Notmuch Emacs email client I use, see this elisp code. To import keys, I pipe the message into this script which is basically just:

sq autocrypt decode | gpg --import

... thanks to Sequoia best-of-class Autocrypt support.

Note on OpenPGP usage

While some have claimed OpenPGP's death, I believe those are overstated. Maybe it's just me, but I still use OpenPGP for my password management, to authenticate users and messages, and it's the interface to my YubiKey for authenticating with SSH servers.

I understand people feel that OpenPGP is possibly insecure, counter-intuitive and full of problems, but I think most of those problems should instead be attributed to its current flagship implementation, GnuPG. I have tried to work with GnuPG for years, and it keeps surprising me with evilness and oddities.

I have high hopes that the Sequoia project can bring some sanity into this space, and I also hope that RFC4880bis can eventually get somewhere so we have a more solid specification with more robust crypto. It's kind of a shame that this has dragged on for so long, but Update: there's a separate draft called openpgp-crypto-refresh that might actually be adopted as the "OpenPGP RFC" soon! And it doesn't keep real work from happening in Sequoia and other implementations. Thunderbird rewrote their OpenPGP implementation with RNP (which was, granted, a bumpy road because it lost compatibility with GnuPG) and Sequoia now has a certificate store with trust management (but still no secret storage), preliminary OpenPGP card support and even a basic GnuPG compatibility layer. I'm also curious to try out the OpenPGP CA capabilities.

So maybe it's just because I'm becoming an old fart that doesn't want to change tools, but so far I haven't seen a good incentive in switching away from OpenPGP, and haven't found a good set of tools that completely replace it. Maybe OpenSSH's keys and CA can eventually replace it, but I suspect they will end up rebuilding most of OpenPGP anyway, just more slowly. If they do, let's hope they avoid the mistakes our community has done in the past at least...