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How does this compare to Tailscale/Headscale?

Tailscale is a virtual network device (works on L3, tun not tap device) whereas chisel just listens on ports (works on L4)

Tailscale is Wireguard this is HTTP. Different protocol?

Tailscale does actually support Wireguard packet forwarding over HTTP (a custom addition to the protocol; standard Wireguard only runs on UDP) for tricky NAT traversal use cases, but that's only used in pretty gnarly situations. Otherwise, it's a regular VPN, i.e. encapsulated and encrypted IP over UDP.

https://tailscale.com/blog/how-tailscale-works#encrypted-tcp...

Very interesting! Always wondered what the value add was and this is one of them

Yes, reliable NAT and firewall traversal is basically the make-or-break feature for "P2P"/mesh VPNs.

And Tailscale is doing a great job at trying to only resort to relaying when there's really no other choice, both because it improves latency and saves them bandwidth on their relays.

It's very similar to VoIP and videocalls (1:1; conferencing usually performs better with SFUs) in that regard.

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