Comment by jkaplowitz

While I don’t work for Tailscale and don’t know their specific reasons, I do know that US export controls and sanctions with respect to Cuba are quite complicated and are designed more due to historical & continuing political pressures than sensible policy.

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.