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PriorProject ,

To a first approximation, Tailscale/Headscale don’t route and traffic.

Ah, well damn. Is there a way to achieve this while using Tailscale as well, or is that even recommended?

Is there a way to achieve what? Force tailscale to route all traffic through the DERP servers? I don’t know, and I don’t know why you’d want to. When my laptop is at home on the same network as my file-server, I certainly don’t want tailscale sending filserver traffic out to my Headscale server on the Internet just to download it back to my laptop on the same network it came from. I want NAT traversal to allow my laptop and file-server to negotiate the most efficient network path that works for them… whether that’s within my home lab when I’m there, across the internet when I’m traveling, or routing through the DERP server when no other option works.

OpenVPN or vanilla Wireguard are commonly setup with simple hub-and-spoke routing topologies that send all VPN traffic through “the VPN server”, but this is generally slower path than a direct connection. It might be imperceptibly slower over the Internet, but it will be MUCH slower than the local network unless you do some split-dns shenanigans to special-case the local-network scenario. With Tailscale, it all more or less works the same wherever you are which is a big benefit. Of course excepting if you have a true multigigabit network at home and the encryption overhead slows you down… Wireguard is pretty fast though and not a problematic throughout limiter for the vast majority of cases.

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