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I am looking on possibility to have access to internet through RDP connection. I have VPN tunnel which allowing me to connect from my workstation (Lets name it Server-A) RDP to one Windows server (Lets name it Server-B), but Server-B don't have internet access through his gateway. My question is, can I somehow direct Server-B internet traffic to Server-A through RDP, and then to internet, so in final I will have something like: Server-B (internet traffic) -> from RDP to Server-A -> to Internet (and back). Please advise possibilities for Server-B to have internet only having his RDP access.

madial9663
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  • So rephrasing your question, you wish to connect to the internet from a server, by going back through the bastion host, tunneling though the RDP session (somehow) so the traffic would then appear to be coming from your local computer where your VPN client is running. Sounds like you're trying to do something similar to SSH remote port forwarding. A more legitimate approach would like be using an outgoing proxy. RDP clients don't expose such functionality, but I could imagine subverting things like copy/paste of files or remote devices to transfer data. – Cameron Kerr Apr 07 '21 at 11:43
  • Thanks Cameron. Actually this is not for just copy/paste files, I wanted my Server-B to synchronize time with public NTP server, as I know NTP is using UDP packets and If I somehow can direct NTP (UDP) related packets to outside (and receive), it will be great. In theory !! what if I upload SSH software (like openssh) and install it on remote server, (and I don't know how) create tunnel and then do this SSH remote port forwarding. What do you think does it make sense? P.S. This will be temporary solution, until permanent gateway setup. – madial9663 Apr 07 '21 at 12:17
  • SSH port forwarding doesn't handle UDP. If I was in your position, I'd probably look at using Ansible to manage the remote server via a SSH Port forward (for setting time, running commands, etc). I'd consider it a semi-crappy (network gynmastics) solution but useful for DMZ type of environments.Whether that would work with RDP though.... not without adding something else like SSH to the mix. However, it seems like this would have you neck-deep in workarounds you don't have much experience with, so this would be very painful and a redesign or better permanent solution should be a priority. – Cameron Kerr Apr 07 '21 at 12:36
  • Yeah, I agree with you. I wanted to know the opinion from experienced, and I got it. Thanks again @Cameron. – madial9663 Apr 07 '21 at 13:37

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