> massive deal

OFAC applies to trade, like your "massive deal". OFAC's original authority comes from a law titled, literally "The Trading With the Enemy Act".

Tor publishes free software, asking nothing in return. That isn't trade. Neither are those evangelists who broadcast sermons on shortwave radio -- they certainly "serve" Iran in the sense that people in that country can hear their broadcasts.

"Cyber product" lolwut? I think you have been breathing too many beltway fumes.