Troubleshooting Microsoft Remote Desktop over VPN



  • I have user, VPN Lady, who constantly has trouble connecting to her remote desktop over the VPN. Some of you might remember my previous post on this topic, Explainging VPNs and Remote Desktops to Non-Technical People

    We actually have two VPN systems: one is a site-to-site OpenVPN which she uses when she is at our branch office. When she uses the site-to-site VPN, the remote desktop connection just works.

    But when she uses our SoftEther client VPN from home, she can connect to the VPN but not to the remote desktop connection. Funnily enough, I borrowed her laptop, took it home, connected to the VPN, and then successfully used the remote desktop connection.

    Based on that, she took the laptop to her parent's house and tried it all. I don't think she ever told me if it worked or not. (It might have become μ at some point)

    I know it's not a Windows permission problem. I just made a Windows user called rdp-test and put him in the same Windows group (called Remote Access) that she is in. In fact, just to double check my work, I triple checked that she's in the Remote Access group.

    She is supposedly using the remote desktop's fully qualified domain name.

    This is driving me up a wall. WTF should I be looking at now. It also doesn't help that she frequently does user error and has been caught lying about following instructions.


  • Java Dev

    @captain Is she connecting to VPN before starting remote desktop?



  • @pleegwat She is supposedly following the instructions. It looks like the logs agree. She successfully connects, does stuff for about a minute, and then disconnects.



  • Her ISP is blocking port 3389? 🐠


  • BINNED

    Use TeamViewer to connect at the pc so you can try to VPN and RDP out ...

    I would advise against RDPing to the pc that you are using to start the TeamViewer from.


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