I'm pretty sure I'm being bit by firewall rules on the router. It seems to be rejecting all of the tunnel packets and it has no reason to try to connect to the laptop the handshake never occurs again. I suspect that normally a connection established related rule lets things through. I just need to figure out how the start up packet is different so that it gets through. The systemd iptables service eventually seems to stop. Probably there is a DNS request that needs to timeout. I do some source address rewriting and it may be that the initial addresses used for the encapsulating packets are different than the ones later.
So most likely this is all on my end and not wireguard related.
Thanks for the tcpdump suggestion. I should have tried that sooner.
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