If you're American, it's easier than ever to go to Cuba, a country that's remained, mas o menos, off limits for the last 60 years or so. In fact, you can go to cheapair.com, buy a ticket, fill out a couple forms confirming you fit into one of several broad approved categories of person (you probably do), and hop on a flight direct to Havana. But should you?

As we've explored in a series of stories over the last couple weeks, Cuba is still very much an island ruled by an authoritarian regime, with nearly all industry and services owned and operated by that regime. There's little starvation or homelessness on the island, but there's also very little free expression, internet access, or free flow of information. Overt propaganda is everywhere, and there are neighborhood watch groups specifically designed to inform on people who are "counterrevolutionary." 

And so, if you go to Cuba to sit on a beach, smoke cigars, and drink mojitos, you are ostensibly putting money directly into the pockets of that regime. Maybe that bothers you, maybe it doesn't. But should it? After spending three weeks reporting in Cuba, I spoke to Jose Luis Martinez of the Foundation for Human Rights in Cuba about this topic and about the general internet connectivity and technological situation in the country.

Afterwards, Motherboard staffers talk about their biggest work technology gaffes—if you've done anything particularly embarrassing, please tweet it my way: @jason_koebler.