Weird Networking Issue with Server 2008 R2 Standard

Until recently, I was able to connect to a Windows 2008 R2 Server either by MSTSC/RDP or VNC... now, as of late, the Windows server is ignoring any Windows XP machine for connections. Pings respond, but if I try to connect via VNC or RDP, it just gets ignored.

This applies to 2 XP machines even (my daily driver, and my downloader).

Machines are on the same network. On the server, I even removed the most recent security fixes that windows updates did back in 2024.

A Windows 11 machine can access it no problem from MSTSC or VNC. In fact, I connect to that windows 11 machine from my XP machine via RDP and no issue. The server 2008 machine has all firewalls disabled completely, even the third party one I installed.

With RDP, it gets as far as asking for a username and password, but nothing more.

I didn't connect to it for awhile, and now it seems to resent me for it.

I'm at a loss, and the google machine isn't helping.
 
I did find something... but still doesn't make sense.

Statically assigned adapter will work, but DHCP assigned adapter doesn't.

But, why?
 
Well damn, I figured it out.

Windows XP doesn't like classless routes?

DNSMasq classless route option turned off, and everything clicked.

dhcp-option=br0,option:classless-static-route,10.10.x.x/22,10.10.x.x # (option:classless-static-route or 121)
 
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