Help with correct routing for Tailscale/Wireguard - really frustrated!

Running two VPS instances.

One in Auckland, and an Oracle Cloud instance in Sydney.

Auckland acts as a wireguard server - using PiVPN's build there, and I connect to the Sydney instance via the standard Wireguard client. I have configured everything and it seems to connect

Here are the settings

Wireguard Config on server

The issue is I have Tailscale running on all my machines, and whenever I connect the Sydney VPS to wireguard, I cannot connect to it via Tailscale, but SSH and everything else responds just fine.

I know the issue is most likely embarrasingly simple, but cannot figure out what to do. I have tried replicating the AllowedIPS to what works on my Windows Machine "0.0.0.0/1, 128.0.0.0/1, ::/1, 8000::/1

but then Wireguard on my Sydney VPS refuses to work, and I don't get a connection, so I had to go back to the original "0.0.0.0/0,::/0"

I'm connected to my Auckland VPS via Wireguard from my location in South Africa, and I can ping, and access Tailscale just fine. Just as I am trying to do on my Sydney VPS.

It may be worth nothing that Tailscale itself seems to be connected on the Sydney VPS, but it's accessing what's on the machine is a different story, and pinging any Tailscale IP address from the affected machine gives me a "Time to live exceeded"

All I Think need to do is set a route between Wireguard, and Tailscale.......... How?

Thanks

4 Reset to default

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