Originally Posted by
SJOGuy
All true, but the OP's question was about traveling on a USA-Cuba-USA itinerary with no connection in a third country. As you said, he doesn't meet the requirements to travel like that. Connecting in a third country doesn't meet the letter of the law either, but it's easier to do.
I traveled SJO-PTY-HAV and back last year on Copa. The airline produced a form for me to sign saying that, as a U.S. citizen, I was traveling to Cuba for an approved reason. As a journalist, I was.
The point was that departing from a US airport has certain requirements which the same passport holder might not face from an airport outside the US.
Not in a practical sense "bound" by anything to do with US as you state above is the case.
The journalist category is different from most of the 12, requiring a different visa afaik, to satisfy the Cuban government, not just the US, perhaps the reason for your form, despite originating your flight in Costa Rica.
So your case is not comparable to the OP's.