OFAC regulates commerce, not speech. Let's Encrypt is not doing "business", they're operating a free informational service. Lots of organizations interpret any information exchange as subject to OFAC regulation, and you and Let's Encrypt have good company in this interpretation, but I think it's unnecessarily ceding ground.
The government may use as wide of an interpretation of commerce as they can get away with. We've seen this happen before [0]. Sure, Let's Encrypt isn't taking money from the entities they offer certificates to. But the OFAC desk jockey assigned to that case only has to concoct some sufficiently plausible-sounding trail of money connecting the backing 501(c)3 and a sanctioned entity in order to levy penalties, and the legal team will not like that risk, even if it's unlikely for OFAC to win on appeal in a court.
[0]: https://en.wikipedia.org/wiki/Wickard_v._Filburn
This is true, of course, and I understand why some companies don't want to take the risk. But I would hope that Let's Encrypt would take the opposite stance. They were born out of the EFF and have EFF & ACLU board members! These orgs live for this type of legal fight.
IANAL, but it seems like the argument from Wickard v Filburn would apply to LE. They may not be taking money but they do impact the commerce of the market for certificates.
I disagree with that ruling, and I have some serious problems with sanctions against entire countries/regions, but it definitely makes sense that LE would interpret it as being impacted by OFAC.
IANAL, but this seems wrong.
In an alternate universe, Let’s Encrypt has a chat with someone and then states, publicly, like a speech, that they think that person owns a domain.
In our universe, Let’s Encrypt lets a client open an “account”, enters into a contract with the client (the contract is the topic of this entire post), and gives the client an API by which the client requests a certificate. Then Let’s Encrypt grants the certificate. Maybe the certificate is somehow speech. The rest sure doesn’t sound like speech to me.
Wasn't there news a bit ago about some people being suddenly excluded from Linux kernel development for presumably similar reasons?