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I am an Australian citizen visiting the USA using the Visa Waiver Program next week. I have flights booked Houston → Mexico City → Havana → Miami.

As far as I understand I will be fine getting into Cuba after buying a tourist card in Mexico City, however I'm concerned about my return to the USA into Miami - I doubt the Mexican airline will supply an Office of Foreign Assets Control at any point going in, and arriving in Miami without one (and a Cuban stamp in my passport) may cause concerns in Immigration.

Ideally I will be able to use an ePassport gate where I do not encounter an actual human Immigration Officer, however this isn't guaranteed.

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    As far as I understand, there are no restrictions on flying from Cuba to the US as a non-US citizen/resident. [This is different from the opposite direction.] I won't put it as an answer yet because ideally I would do some research to get some references on that. If you use APC, you will still see (and may be questioned by) a CBP officer. It is not fully automated unless you have Global Entry. – Calchas Feb 9 '17 at 12:09
  • @pnuts Perfect. Well since you have it I'll let you write the answer and claim the internet points. – Calchas Feb 9 '17 at 12:14
  • @Calchas After reading pnuts' link it sounds like I should be fine getting in to the US but I will report back next week after I've done it – kaifus87 Feb 9 '17 at 12:28
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    @pnuts Of course. This link indicates that US citizens can avoid questions on their return by having their Cuban visa stamped instead of their passport, and this link and many others like it speak of the OFAC being the only way to get into Cuba and back to the US for both US citizens and third country nationals. None of these speak of a non-US -> Cuba -> US route. – kaifus87 Feb 9 '17 at 12:51
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    @kaifus87 US citizens (and other persons subject to US jurisdiction) are still not permitted to visit Cuba except for specific purposes. That is why they can be questioned. – Calchas Feb 14 '17 at 11:07
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Yes:

"Cuban nationals applying for admission to the United States, as well as third-country nationals, with a valid visa or other travel authorization issued by the U.S. government may be transported to the United States from Cuba. [...] This includes individuals eligible to enter the United States under the Visa Waiver Program (VWP), as administered through the Electronic System for Travel Authorization (ESTA)."

https://www.treasury.gov/resource-center/sanctions/Programs/Documents/guidance_cuba_travel.pdf

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    Just to add to this with my own experience: I, an Australian citizen travelling to the USA on the ESTA Visa Waiver Program (VWP) was able from Havana to Miami without issue (Feb 2017) – kaifus87 Mar 15 '17 at 5:08

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