Good Morning Guys, I am trying to work out how to force the Remote Desktop Client (mstsc.exe) to use the local proxy settings of the desktop machine and connect though a proxy server. The Situation: There is a user that works offsite who need to remotely access our RDS Server via the RDS Gateway. The site that this use is situated on has a proxy server for all traffic and a firewall configured to only allow traffic from the proxy server. The client can access the RDWeb page and all the application icons however when they click on the icon the session fails. Running a netstat -an | find "externalIP" shows that the client is using port 443 however is trying to go directly to the IP address and not route though the proxy. This is also seen on the firewall. Currently the machine has been set to automatically detect proxy settings. I have changed this to manual proxy settings and un-selected the "Automatically Detect Proxy Settings" The client is running Windows XP with SP3 and we have also tried running a Windows 7 Machine with the latest patching and Remote Desktop Client. Any help would be appreciated.

Perhaps you need set something like netsh winhttp set proxy myproxy.domain.com:443 Regards Milos

Hi Milos, When I ran the command I got an error saying that winhttp could not be found. I set the proxy settings with proxycfg.exe and still have the same issue where the rdp client tries to go to the direct address and not though the proxy.

Hi, As far as I know, Netsh winhttp commands cannot work in Windows XP. Please try the command in Windows 7 machines and see how it works. However, if your clients are Windows XP, it is recommended to ask the question in Windows XP forum. Hope this helps. Jeremy Wu TechNet Community Support

Hi Jeremy, I have tried to the commands on a Windows 7 Machine which appeared to have the same effect as the proxycfg on the Windows XP Machine. In both these cases, the RDP client still tried to route directly to the destination and not use the proxy.

Any more ideas?

Hi, Just following up on previous posts for anyone else following this thread. I have found a "not exactly ideal" solution to the issues I am experiencing. It appears that the RDP client makes a single attempt to go to the proxy, after which the RDP client attempts to route directly to the gateways address. This single attempt passes NTLM authentication though to the proxy. In my case the proxy only supports basic authentication and it was failing the authentication process. It also doesn't help that the environment does not run active directory as it appears that this would have overcome the issue of authentication mismatch. The solution: I am currently using a application used for web debugging called fiddler. This application creates a local proxy server that no authentication is required, you can then authenticate the application against the environment's proxy and it will tunnel the traffic inside that session. I hope this helps.

Hi, Just following up on previous posts for anyone else following this thread. I have found a "not exactly ideal" solution to the issues I am experiencing. It appears that the RDP client makes a single attempt to go to the proxy, after which the RDP client attempts to go directly to the This single attempt passes NTLM authentication though to the proxy. In my case the proxy only supports basic authentication and it was failing the authentication process. It also doesn't help that the environment does not run active directory as it appears that this would have overcome the issue of authentication mismatch. The solution: I am currently using a application used for web debugging called fiddler. This application creates a local proxy server that no authentication is required, you can then authenticate the application against the environment's proxy and it will tunnel the traffic inside that session. I hope this helps.