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Anyone else hoping for that H1B this year?
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Direct flight or through a third country, eg Mexico? If the latter, risk of problems is way lower.
You will not have any problems whatsoever on the Cuban side. They desperately need tourism money.
What is your purpose of travel?
To answer your question, everybody (citizen, residents, or even foreigners flying to Cuba through the US [eg a German wanting to go to Cuba after visiting the US]) is under US law that forbids visiting Cuba without valid reasons.
In my opinion H-1B is worse because it is much easier to deny border entry back into the US than denying entry for green card holders or citizens.
Plenty of people still visit Cuba, but they have valid reasons (with official letters to back it up), or they do it smartly.
I myself wouldn’t go to and from Cuba directly if I were on H-1B (or even as a citizen), because I wouldn’t know how to answer border patrol if they asked why I went to Cuba and ask for documentation.
Also I’m aware that even if it’s ok for other people anecdotally it doesn’t mean that it’d be okay for everyone else.
Went last year, did not even have my info checked on return flight from Havana to US. Global entry is good to go