All good thoughts, thank you

Makes sense. Its unfortunate though that it presents a hurdle for end users. My users need to hit a webpage and acesss stuff, asking them to connect to a VPN client is too much.

Is tail scale really that much more secure than reverse proxy and auth control?

I gotta agree, as much as racism and misogyny overlap, I think a lot of people will vote for someone brown before they’ll vote for a woman.

Unfortunately no. I’m in a similar place to you, currently using Proton and SimpleLogin but hoping to switch to a custom domain and move from Proton. Tuta has been a strong recommendation here but I don’t have personal experience with them yet.

Just to mention it, addy.io is partnered with Tuta much like SimpleLogin is partnered with Proton.

I’ve used Authelia. I like it because all the config can happen in a config file so I can easily back it up, modify it, and deploy it with Ansible