I assume that you are using the IP addresses of the remote machines so that you’re not relying on DNS resolution. If server B had a wacky subnet mask, that may cause an issue like this, but I assume it’s supposed to be /24 (255.255.255.0) and that you’ve got it set that way.
If DNS or the subnet mask don’t apply, you often can get good info looking at the VPN logs. I would check the remote one first and if you see nothing, then check the local one. *From:* [email protected] [mailto: [email protected]] *On Behalf Of *J- P *Sent:* Sunday, January 11, 2015 1:54 PM *To:* NT *Subject:* [NTSysADM] VPN connectivity oddity So on my site to site vpn to one of my clients, I'm running into a baffling issue Home lan 192.168.4.0 remote/vpn lan 192.168.0.0 I CAN remote/ping into a server A which is 2012r1 with IP 192.168.0.12, however, I CANNOT remote/ping to server B which is 2012r1 with IP 192.168.0.5 So to get to server B, I have to remote into server A and do rdp from server A to get to server B (which also shows that RDP and ports etc.. are enabled) I have checked both firewalls (all controlled by domain policy) I have even tried disabling the firewall as well with no success. Both servers are plugged into the same switch, same OS, same patch level. I'm a bit stumped on this one, even though it's not a HUGE inconvenience to RDP from one server to the other, I still want to know WHY this is occuring TIA

