I wouldn't be too surprised if tailscale has become a critical vector of the internet like cloudflare over the years as most ai companies seem to use it
Yet another single point of failure.
I don't see the reason for Tailscale instead of plain old simple Wireguard, it's WG under the hood anyway.
Tailscale is best used as an additional layer of security rather than your only layer. I host everything behind tailscale as if it was the public internet, with proper authentication, https, etc.
So a failure in tailscale is not an issue on it's own because you'd then also have to find an exploit in what I'm actually hosting as well. Both of those things happening at the same time is much less likely.