Tailscale raises $100M

> For people who believe there’s a catch — and most still do — then I don’t know how to write a blog post or hire a marketing or sales team to change their minds.

I think the catch is that (at least at the free level) one must trust an identity providers. For many companies that's probably fair enough, but for high-security companies and private individuals one absolutely cannot trust anything running outside of one's physical control. Service providers can be suborned, either legally by corrupt regimes or illegally by employees. There is no way that I would permit Google, Microsoft or GitHub (their three supported options) to gate access to my private devices.

I think that one must also trust Tailscale themselves, although I could be wrong about that.

Yep we had it rejected w an enterprise we work with as the org needed to own the full control plane so we couldn't bring it in, and not on the schedule for the org's security team for them to bring it in. Making a smarter, easier, and less creepily managed VPN more palatable to enterprises would be awesome, so the marketing value of their fundraise is real.