> pretty sure this is stems from the insane US legal requirement to not export SSL technology to enemy countries
This is most likely OFAC. Lets Encrypt could apply for a license to do business with sanctioned entities, and given their use case it would most likely be approved.
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.
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.
Wasn't there news a bit ago about some people being suddenly excluded from Linux kernel development for presumably similar reasons?