First, welcome.

Second, all of these threads look the same because part of Wireguard’s “elegance” or “lack of complexity” or whatever other words the stans want to use includes the fact that its logging sucks and doesn’t give you any useful information about what the problem is. So everything ends up being a “rekey timeout”. IPSec logs may be impossible to understand, but at least they contain the information you need to fix the problem.

That said, the two most common problems for something like this are:

  1. a settings mismatch or
  2. a firewall/network issue preventing the traffic from getting to the server.

I would check very carefully to make sure you’ve got all the settings correct on the client side, especially if you entered them manually. I was setting up a test server yesterday and entered both the IP and the port wrong by one number.

Second, I would make sure everything is working on your server side in terms of firewalling / port forwarding. If you’re on your LAN, you might try directly entering in the local address of your Pi to make sure you can connect without any issues there.

Once you confirm both of those things, we can start trying to take the problem apart to see if we can find a solution.