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  • Could it potentially be your router or ISP blocking the VPN traffic? Some routers have VPN specific options like pass thru that need to be enabled, you could potentially enable verbose firewall logging on your router too if its available to see if its getting blocked there. If its ISP I'm not sure how to go about fixing that but I dont think thats common, does it work if you configure it on another non PI machine that's cabled in? Commented Aug 10, 2018 at 13:00
  • I think that's unlikely, seeing as it works fine if the server is on wifi and fails if it's wired. Both going through the same router with the same port forwarding. Commented Aug 10, 2018 at 15:09
  • The difference is in the connection of the Raspberry, yet everything you show is the log from your Mac. Commented Aug 11, 2018 at 18:47