Will bringing three good used laptops be a problem in Cuba?

That sounds like an automatic Aduana inspection once the x ray machine sees 4 computers. If you have a chalked x on your luggage you'll be heading into the small room off to the side just before the exit from the arrivals area.

You should expect to pay duties on them. Four computers would signal that you are in the used electronics business.

Never tried more than 2, one in a suitcase and one as a carry on. That was not a problem. But I am in the camp of those who believe that 4 would be an inescapable red flag.

The legal limit is two of anything. Over that you're subject to duty and they'll hit you hard.

I'd put the two cheapest ones in my checked luggage and the two nicest ones in my carry-on. That's the best chance of you slipping through without hassles.

Good luck.

Cheers,
Terry

What Terry said.

I once had a crappy laptop in my checked baggage on the way to Cuba. It was stolen.

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