This is naive

As even you said, Cuba was not supposed to have Windows copies, but I'm sure they had

Iran theoretically couldn't have access to Boeing parts (and this was a stricter embargo), but they had

There's always a way of solving things.

Most of Cuban problems were caused by themselves, not the embargo.

>> This is naive

What? This was the real world, a matter of first hand experience. We could not consider jeopardising sales to our biggest market (the US) by breaking US embargo for a barely significant market.

You're right, you shouldn't consider doing it unless there are significant gains to be had.

But see my other comment.

(However, I don't think Cuba has qualms about pirating software, if this was hw it would have been a different issue)

> There's always a way of solving things.

Except, not really.

You can’t put any app using any encryption technology up on the Google Play Store or the iOS App Store, if you also distribute anything to Cuba.

For the first you need to get an approval from the US DoD, which requires that you never interact with Cuba.

Yes, but you don't sell it directly to Cuba, you sell it to $COUNTRY which might eventually sell it to Cuba (and you don't even know about it)

It's not you selling to Cuba, it's Cuba buying through intermediates.

(Of course if you really want you can sell things directly to Cuba, but you need to find a way of disguising it)

You're (or, were) also forbidden from bringing Cuban cigars to the US, but if you arrive from a flight from Panama with a box of unmarked cigars nobody is going to do anything.

You could sell apks

I can’t sell anything to Cuba while also providing anything in the Google Store or the Apple App Store.

That’s part fo the issue.

You could write your software in another operating system, giving a middle finger to oppressive Uncle Sam. Not doing so shows you did not appreciate Cuban market enough.

Same goes for other products. Don't base them on U.S. technology if you plan to trade with America's enemies.