SSL VPN with RDP connection - VPN: Site to Site and Remote Access

VPN RDP Connection

Rdp / April 7, 2019


Just to confirm, you stated you cannot remote desktop into your office computer which is joined to a Microsoft Windows Server 2003 domain. In an effort to troubleshoot your issues, let’s check the following:

1. Ensure that when the VPN is established you can open a command prompt and PING to the target Windows Sever 2003 / work machine and confirm whether or not you can get the desired IP address from the reply.
2. If the test is fine above, telnet to port 3389 (standard RDP port) to test whether it can successfully connect. Again, this command is to be run from within command prompt. “C:\>telnet 3389” (Without the quotations and where is substituted by your actual FQDN (Fully Qualified Domain Name) or External IP address. The result of this command should give just a blank screen if you are successful. If the port is not open, you’ll get an error message.
3. Check all firewall and anti-virus applications that may be running on the Windows 7 machine. As a troubleshooting method, disable all firewalls.
4. If possible, attempt to connect to the server / work machine in question from within your network from the Windows 7 machine. Performing this troubleshooting step will indicate whether or not the issue is VPN specific. If the connection from within the network fails, it is likely not VPN specific.