>> technically, buying cigars in Canada is OK
It is “technically” not OK. You can be prosecuted. Search for the thread about the guy who was in Canada and tarded with Cuba and was arrested when he returned to the US. I believe it was in the pit.
At any rate, the law is clear, citizens and residents of the US cannot legally trade in anything that has or had any trace of Cuban interest. You can find the regulations in OFAC
[quote]
http://www.ofaccompliance.com/WhatIsOFAC.htm
OFAC laws and regulations apply to: 1) all corporations and businesses under US law; 2) all American citizens and permanent resident aliens wherever located; 3) all individuals and entities located in the US.
[quote]
See also
http://www.treas.gov/offices/enforcement/ofac/sanctions/sanctguide-cuba.html
Helms-Burton even makes it unlawful for foreign nationals abroad to trade with Cuba. While it is mostly ignored I know of some foreign businessmen who have been denied visas to the US on account that their companies traded with Cuba.