Tailscale has another interesting feature that I figured out entirely by accident: while the SSO planes (at least using Apple as SSO, rather than your own) may be blocked, the data planes and actual control planes usually are not. If your device is connected to your tailnet before joining a given WiFi, it will stay connected afterward.
The guest WiFi at work blocks OpenVPN connections, but established Tailscale slips by. I haven't tried straight Wireguard because I don't consider Tailscale having timing and volume data on me to be all that valuable to them, and they do mitigate the double-NAT situation. I do run a private peer relay for my tailnet but not a full DERP server, nor do I run Headscale.
Obviously, your personal security concerns play a role here, but I'm not doing anything I wouldn't do straight from my home network, so I see no reason to make my life harder. If you need that level of security, you need a different solution.
I noticed the same, I had nodes on 2 different ISPs.
On one ISP inbound IPv6 was blocked at router, while on other IPv6 was fully allowed.
Tailscale detected this is automatically created the tunnel from the blocked one to the other.
I was super impressed, as this was handled automatically.
Genuinely curious: is Tailscale actually providing any values to this use case beyond what you get from a raw Wiregaurd exit node with port forwarding instead of Tailscale's NAT traversal? I've never used Tailscale, but I have a Wiregaurd setup on my home server for the same purpose as described in the article, and I've never had any issues with it.
Edit: Noticed some sibling comments asking effectively the same thing as me. I've been meaning to write a blog post covering the basic networking knowledge needed to DIY with just Wiregaurd. My impression is that many people don't realize just how easy it is or don't have the requisite background information.
Tailscale is interesting. It's built on top of wiregaurd but is different in that it creates a mesh of vpn connections between your devices, rather than just a connection from client to server.
I haven't used it because I use witeguard the traditional way and haven't needed a mesh of devices. Also I haven't taken time to investigate the private company offering it and what sorts of my information is vulnerable if I use it.
Interesting article; do you have any details on the performance differences?
Tailscale tangential use case! :)
I was looking for remote access software to help family with their PC and came across RustDesk(https://rustdesk.com/) but it needs a server. Found out it can work without a server if you have Tailscale installed. No fees for any of this and works on many platforms.
Tutorial for Rustdesk + Tailscale setup for remote desktop access: https://www.youtube.com/watch?v=27apZcZrwks