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Normal traffic stalls, wireguard traffic through same server works fine

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I have a weird networking issue, possibly due to problems at my ISP or with my router (an Eero 6), which manifests itself in the following way. On a machine X connected by wire to the router R, requests to certain web sites stall (sometimes the ssh handshake completes, sometimes not, but it always stops there).

This machine X also acts as a wireguard server, and the router R forwards connections on the wireguard port from the outside to X. If I connect from a different machine Y via wireguard to my static IP address and then the wireguard server X, all is good, and the above network issues do not arise!

This happens even when Y is on the local network, so connected to the same router R. If Y is directly connected to R, many web site requests stall. If I leave it connected to R, but then setup a wireguard tunnel via the external IP via R to X, all is good.

If I make requests directly on the server X, connections stall too...

I have IPv6 turned off on the router R and on X and Y, so all traffic is IPv4. DNS works fine in all cases (and returns the same IP addresses regardless of how I am connected), so it is not a DNS issue.

Any ideas? Or any tools that I could use to see what is the difference between packets going in/out directly and going via wireguard?

I sit in a Tesla and translated this thread with Ai:

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