Server 2008 R2 RDP 443 Connectivity Issues RRS feed

  • Question

  • I have a Server 2008 R2 device that I'm trying to use Remote Desktop Connection to connect to on port 443 and it's not working properly from all my PCs. I'm able to connect to the device with RDP when connecting from a switch that is directly connected to the server by typing in the address and then :443 with no issues. I am also able to connect with another PC that is connecting through an IPSEC VPN tunnel from a different network, which is connected to the network the server is on. However, can't connect from a different PC is routed from a different network into the local network where the server is.

    I've done multiple packet captures on the server. When connecting from the PC through the VPN I get the 3 way TCP handshake followed by some TLSv1 protocol and TCP ACK packets, and then the PC and server start exchanging certificate information and I'm able to RD in to the server.

    When connecting from the PC that is routed from another network to the server I get the same 3 way TCP handshake which works fine, and then immediately, as in .000001 seconds later, my PC sends a TCP FIN,ACK packet and the session ends with the server sending a TCP RST,ACK packet. On this PC I get an error at that time saying "This computer can't connect to the remote computer. Try connecting again. If the problem continues, contact the owner of the remote computer or your network administrator."

    Currently the server RD Session Host is set to use SSL (TLS 1.0) encryption. Port 3389 is not an option because it's blocked by firewalls between the PC and the server.

    Any suggestions?

    Thursday, January 7, 2016 6:23 PM