The NK state is more than capable of arranging their own VPNs.
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.
The vast majority of north koreans only have access to the nationwide intranet. Those that do have outside connection are few trusted elites who are there to do business. And no matter who you are (this also applies to foreigners in the country), your device and connection is heavily monitored by the state. Merely posessing a non-state sanctioned device as a north korean is considered a serious criminal offense. At that point the only use case of a VPN for someone with a north korean IP is for cybercrime and not dissidents.
Bad comparison. NK is a nuclear state with nuclear weapons that is constantly threatening its neighbors. Cuba flirted with the idea but they didn't really materialize any nuclear or military capabilities. This was also a long time ago.
