4 ms·

To be fair, advanced real world knowledge of public/private key PKIs (x.509 or other), things like root CAs, are a fairly esoteric and very specialized field of

To be fair, advanced real world knowledge of public/private key PKIs (x.509 or other), things like root CAs, are a fairly esoteric and very specialized field of study. There's people whose regular day jobs are nothing but doing stuff with PKI infrastructure and their depth of knowledge on many other non-PKI subjects is probably surface level only.

hannob 6mo ago
I know quite a bit about PKI and X.509, and I can tell you that much: the overlap with how DNSSEC works is limited.
- silisili 6mo ago
  As is the overlap between DNSSEC and DNS itself, to be honest. I once worked at the level of administering DNSSEC for 300+ TLDs. It's its own world. When that company was winding down, I tried to continue in the field but the most common response (outside of no response, of course), was 'we already have a DNS team/vendor/guy.' And well, then things like this happen. I won't throw stones though, it's a lot to learn and can be incredibly brittle.
hathawsh 6mo ago
Is that actually true, though? Even though it's not really my job, I find myself debugging certificates and keys at least once a month, and that's after automating as much as possible with certbot and cloud certificates. PKI always seems to demand attention.
- walrus01 6mo ago
  In my initial comment, I meant more in terms of complexity and planning from the perspective of the people who are running the public/private key infrastructure on the other side/upstream of what you're doing as a letsencrypt end user. Broadly similar general concept to the team responsible for the DNSSSEC signing keys for an entire ccTLD. Yeah a x509 PKI / root CA is a very different thing than DNSSSEC but they have a number of general logical similarities in that the chain of trust ultimately comes down to a "do not fuck this up" single point of failure.
mschuster91 6mo ago
It's not made easier by the fact that a lot of cryptography is either very old and arcane or it's one hell of a mess of code that doesn't make sense without reading standards. I had the misfortune of having to dig deep into constructing ASN.1 payloads by hand [1] because that's the only thing Java speaks, and oh holy hell is this A MESS because OF COURSE there's two ways to encode a bunch of bytes (BIT STRING vs OCTET STRING) and encoding ed25519 keys uses BOTH [2]. And ed25519 is a mess in itself. The more-or-less standard implementation by orlp [3] is almost completely lacking any comments explaining what is going on where and reading the relevant RFCs alone doesn't help, it's probably only understandable by reading a 500 pages math paper. It's almost as if cryptographers have zero interest in interested random people to join the field. End of rant. [1] https://github.com/msmuenchen/meshcore-packets-java/blob/main/src/main/java/de/afa_amateurfunk/meshcore_packets/crypto/PublicKey.java#L57 https://github.com/msmuenchen/meshcore-packets-java/blob/mai... [2] https://datatracker.ietf.org/doc/html/rfc8410#appendix-A https://datatracker.ietf.org/doc/html/rfc8410#appendix-A [3] https://github.com/orlp/ed25519/tree/master https://github.com/orlp/ed25519/tree/master
- cyberax 6mo ago
  X.509 is a deep legacy, but at least at this point it's well tested. > because that's the only thing Java speaks No, it most definitely is not. You can just construct a private key directly in BouncyCastle: https://downloads.bouncycastle.org/java/docs/bcprov-jdk18on-javadoc/org/bouncycastle/crypto/params/X25519PrivateKeyParameters.html https://downloads.bouncycastle.org/java/docs/bcprov-jdk18on-... I'm 100% certain that you also can do that with raw java.security. I did that about 15 years ago with raw RSA/EC keys. You can just directly specify the private exponent for RSA (as a bigint!) or the curve point for EC. Ditto for ed25519, you can just take the canonical implementation from DJB. And you really really shouldn't do that anyway, please just use OpenSSL or another similar major crypto library.
  - Muromec 6mo ago
    I wouldn't recommend touching openssl (the library, command line tools are okay-ish) with anything that breaths life.

hannob 6mo ago

I know quite a bit about PKI and X.509, and I can tell you that much: the overlap with how DNSSEC works is limited.

silisili 6mo ago
As is the overlap between DNSSEC and DNS itself, to be honest. I once worked at the level of administering DNSSEC for 300+ TLDs. It's its own world. When that company was winding down, I tried to continue in the field but the most common response (outside of no response, of course), was 'we already have a DNS team/vendor/guy.' And well, then things like this happen. I won't throw stones though, it's a lot to learn and can be incredibly brittle.

hathawsh 6mo ago

Is that actually true, though? Even though it's not really my job, I find myself debugging certificates and keys at least once a month, and that's after automating as much as possible with certbot and cloud certificates. PKI always seems to demand attention.

walrus01 6mo ago
In my initial comment, I meant more in terms of complexity and planning from the perspective of the people who are running the public/private key infrastructure on the other side/upstream of what you're doing as a letsencrypt end user. Broadly similar general concept to the team responsible for the DNSSSEC signing keys for an entire ccTLD. Yeah a x509 PKI / root CA is a very different thing than DNSSSEC but they have a number of general logical similarities in that the chain of trust ultimately comes down to a "do not fuck this up" single point of failure.

mschuster91 6mo ago

It's not made easier by the fact that a lot of cryptography is either very old and arcane or it's one hell of a mess of code that doesn't make sense without reading standards. I had the misfortune of having to dig deep into constructing ASN.1 payloads by hand [1] because that's the only thing Java speaks, and oh holy hell is this A MESS because OF COURSE there's two ways to encode a bunch of bytes (BIT STRING vs OCTET STRING) and encoding ed25519 keys uses BOTH [2]. And ed25519 is a mess in itself. The more-or-less standard implementation by orlp [3] is almost completely lacking any comments explaining what is going on where and reading the relevant RFCs alone doesn't help, it's probably only understandable by reading a 500 pages math paper. It's almost as if cryptographers have zero interest in interested random people to join the field. End of rant. [1] https://github.com/msmuenchen/meshcore-packets-java/blob/main/src/main/java/de/afa_amateurfunk/meshcore_packets/crypto/PublicKey.java#L57 https://github.com/msmuenchen/meshcore-packets-java/blob/mai... [2] https://datatracker.ietf.org/doc/html/rfc8410#appendix-A https://datatracker.ietf.org/doc/html/rfc8410#appendix-A [3] https://github.com/orlp/ed25519/tree/master https://github.com/orlp/ed25519/tree/master

cyberax 6mo ago
X.509 is a deep legacy, but at least at this point it's well tested. > because that's the only thing Java speaks No, it most definitely is not. You can just construct a private key directly in BouncyCastle: https://downloads.bouncycastle.org/java/docs/bcprov-jdk18on-javadoc/org/bouncycastle/crypto/params/X25519PrivateKeyParameters.html https://downloads.bouncycastle.org/java/docs/bcprov-jdk18on-... I'm 100% certain that you also can do that with raw java.security. I did that about 15 years ago with raw RSA/EC keys. You can just directly specify the private exponent for RSA (as a bigint!) or the curve point for EC. Ditto for ed25519, you can just take the canonical implementation from DJB. And you really really shouldn't do that anyway, please just use OpenSSL or another similar major crypto library.
- Muromec 6mo ago
  I wouldn't recommend touching openssl (the library, command line tools are okay-ish) with anything that breaths life.