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@xenos: okay so your debian guest probably is an LXC container? the netmask for that is given in your network config as CIDR mask, should be /32 then!
in the proxmox GUI you normally have to fill in the IP and a CIDR mask, make sure it says A.B.C.D/32 there, like this
after a restart of the container have a look at that netmask setting inside again.
I just checked different VMs and LXC on one of my proxmox nodes and they are able to ping each other regardless if the IPs are in the same subnet or not. yet I don't have any windows VM there to try if that would make a difference...
your traceroute looks even more weird, if I do the same I reach the other VM directly in the second hop.
@Falzo Changing the CIDR fixed everything. I really appreciate your help!
you're welcome!
correct netmask setting tends to be an underestimated thing some times ^^
@Falzo was great as usual