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Tailscale appears to be a VPN network built on wireguard. As its a cloud based VPN server, and they run the servers the issue if logging is thee same as with any VPN provider. Further, they actively advise they do logging (and let you see it) - "Tailscale’s central logging service has controllable retention periods and each node just logs some ...


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I am not quite sure what your LWIP network stack is supposed to do in this scenario, and how it is related to being a transparent proxy, so partial answer: From a networking perspective, your TUN device just looks like another network interface. So the computer assumes there's a LAN segment attached to this device, there's other computers on this segment, ...


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