I think that we had receipts from the casas, SC - the very first thing we had to do when we arrived was to produce our passports and sit down with the owner so that they could fill in the form for the government. I'm pretty sure we got a copy of it, but I could be wrong - I even remember duplicating paper being in evidence and it was a long time since I'd seen anyone using that.

also when we booked tours and transfers, though not for taxis etc, and not in small paladars.

what amazes me is the thought that the average border control person is going to be bothered with this stuff - haven't they got better/more important things to do?

It does not fall to passport control to enforce these rules. It falls to the OFAC division in the Treasury Department. That is the government office that could conceivably contact you after your return. That is the office that will be charged with clarifying the new rules in about 30 days.

BTW, the new rules will not apply to anyone who paid money toward their trip prior to June 16th (we did - both a deposit on the tour portion, and the air tickets).

honestly that legislation which it seems has been attempted many times means nothing compared with yet another presidential mandate...lets get serious people..Trump can pretty much override anything and do what he wants when it comes to Cuba ..that is not politics it is fact. And even though people have deposits made etc. I have to wonder what kind of flights the airlines will be putting on next year if load factors are down because most are not interesting in the very expensive group tours. Group tours will not fill aircraft...not at all...most on our plane this year were staying in casas and doing same as we did on our own. As much as I would like to think this will all just go away I don't think it will...Trump will continue this type of behavior on things he can control because some of the really big stuff he can't. The uncertainty will kill this market and people are already cancelling Air BNB or other land arrangements while they still can without excessive penalties.

I don't disagree with you at all, except it's all politics :-)

(We're going in August, I don't think anything will have changed by then).

August should be no problem ...as for receipts...well when the casa owner took passports for recording we got nothing...no receipt for final payment although I am sure they could have taken something and wrote one...no receipts for guides although again they would write something....but honestly I knew no one was asking. Politics or whatever it is a sad way for our leaders to spend their time when we have so many issues more important.

The opening to Cuba that began 2.5 years ago was accomplished entirely by executive order, which meant that it was fragile and could be undone by executive order in a different administration. That's exactly what happened.

yep the stroke of a pen and encouragement from Little Marco and you have a different ballgame.