Except the reason it's not done today is because back in the 90s, people argued that it's not possible to tell if/when services/IP crossed borders because there's no fixed port of entry.
(They were making this argument because software CDs were subject to import duties but downloads were not and that they were unfair)
Today it's still the case and services/IT are not subject to duties.. but I think large licensing agreements like this should definitely attract import duties
The solution is simple enough: look at the companies books, if money is leaving the country, duty is charged unless it can be accounted for by something else (like the existing duty on physical goods).
IRS: Hey Google, you said you made this much money, so you owe us tax.
Google: No, see, here we paid it to Google Ireland as IP license fees, so we in fact made $0
Except the reason it's not done today is because back in the 90s, people argued that it's not possible to tell if/when services/IP crossed borders because there's no fixed port of entry.
(They were making this argument because software CDs were subject to import duties but downloads were not and that they were unfair)
Today it's still the case and services/IT are not subject to duties.. but I think large licensing agreements like this should definitely attract import duties