Ah! This could have been great for me, except that Tailscale recently cut off access to Cuban nationals to their service (they have their reasons, I guess.) Still, I think that the service they're building, step by step, is fine actually.
I used to be involved in leading a US charitable nonprofit that, during the Obama years, once wanted to pay for someone to attend a technical conference in Cuba (or maybe it was to pay for a Cuban to attend a technical conference elsewhere - I forget). We did actually make it happen, but it involved consulting with lawyers, comparing the details of the situation against the applicable rules, and getting people to promise to stay within those rules.
My guess is that either Tailscale or one of the providers they depend on is cutting off Cubans as an attempt to comply with these Cuba-specific US legal obligations, or at least to reduce their risk of falling into non-compliance.
At the very least, GitHub has found ways to legally make most (not all) of their offerings available to Cubans / in Cuba despite the sanctions, except for more narrowly banned individuals and groups. So if you can obtain the open source code for Tailscale (client) and Headscale (server), you can at least use that to benefit from Tailscale’s software.
Even Google follow some of those: https://support.google.com/google-ads/answer/6163740?hl=en
Cuba really doesn't have much of a choice, they have to trade with "friendly" nations of which America refuses to be.
Fun fact, when we (Canadians) go to Cuba they typically won't stamp our passports because they know it causes us issues when trying to enter the US.
(Or, at least, offer subsidies to their government if they stop supporting Russian and Chinese spies with their numbers stations et al.)
Mind you, I am not saying there is an existential possibility of a better policy, but the calculus would be nowhere as trivial as this.
I mean, certainly, but it's like having a club on your car's steering wheel: it's not about creating perfect protection, it's about ensuring your car isn't the softest target for theft in the parking lot.
If Cuba had fewer reasons to talk to Russia and China, then Russia and China would have fewer reasons to talk to Cuba in particular, vs. other Caribbean and Central American nations. Which would, potentially, spread their resources thinner and decrease covert-ops ROI, as they'd be having to engage with several nations who only weakly want them there, instead of one nation that desperately wants them there.
(And yes, I do realize that these powers do already engage with other nations in the area, e.g. Nicaragua. But not in the same way / not for the same reasons.)
Also, if you want to talk about countries that the US actually gives "special attention" to, I'd more compare/contrast to the relationship between the US and Panama.
Cuba would have do what those other ex-USSR satellites did and discard communism and authoritarianism in favor of democracy. Then, yes, seeing themselves as a sovereign state would be a good thing.
But I'm not sure if such an alignment could be created between the US and Cuba while Cuba remains a communist authoritarian hereditary dictatorship, since there's no shared enemy nearby and no strong shared economic incentive. Seems like the only real alignment would be Cuba becoming a democracy.
I think the West gains a lot more by having generally available VPN access in adversary states than it loses from their ability to purchase technical services that they still will have difficulty getting access to currency to pay for and they still will have difficulty actually shipping anything to NK.
Yes? Making it easier for North Korean citizens, or even just leadership, to communicate privately with each other and with people outside makes it easier for them to negotiate or even defect, and would help de-escalation efforts.
> What might the reasons be on the "no" side?
I guess one could argue that the North Korean government doesn't have access to secure VPN systems for government use (pretty implausible IMO) and that increasing their costs is inherently worth it? Realistically most of the opposition would come from those who benefit from the status quo (e.g. arms suppliers) and don't want to see that de-escalation, and I guess the extremely risk averse who would rather keep kicking the can indefinitely and hoping the blowup doesn't come until after they're dead, than risk actually trying to help North Korea's people.
Requires a lot more setup, but it is an option. I've been self-hosting headscale for some time and it is quite stable.