Tailscale has raised $160M

Still can't wrap my head around that TS does not allow to signup with your custom email/password combination but forces you to use bigtech (GitHub, Apple, Meta etc.) to login. Running your custom OIDC provider as a small, private person does not make any sense either.

I think that's quite smart, and OIDC is an open standard at least.

Securing usernames/passwords and handling second factors etc; is already done so well and it's hard to do.

Having a clear 'this is where we can be secure' stances is what makes me want to trust them more.

Why is that smart? I signed up for a Microsoft Account with my email and I can use Microsoft Account to log in to Tail scale but I can't use the email directly? How does the middle man bring anything to the table?

Because then tailscale doesn’t store a username and password for you, so unless microsoft is hacked you won’t be- theoretically.