Never heard of anyone arrested and the fine can depend on how much you bought.
EDIT: From poker's links below, definitely arrests from re-sales inside the states but from anyone ordering from a vendor, I have never heard of it.
Quote:
With civil penalty releases completed for 2010, only one transaction for the unauthorized purchase of Cuban cigars over the Internet was levied, back in March. The transaction took place in late 2004 or early 2005 and the individual cited paid a fine of $525. That was it for the entire year.
The one fine equaled the 2009 total, where only a single purchaser - again in late 2004 or early 2005 - was hit with a penalty of $1,175.
By contrast, OFAC issued 27 penalties in 2008 for a total of $39,763.08, nearly double the 14 penalties issued in 2007 (for $20,330.70).
|
http://www.cigarcyclopedia.com/news-...cigars-in-2010