Scheduled VPN Disconnect when trying to connect by Remote Desktop Services On windows Server 2016-2019

Sajjad Pirahesh 1 Reputation point

I have two computers which connecting to each other through VPN. This VPN is running automatically through job scheduled in SQL-Server. Both of these computers run Windows Server. When I want to connect to VPN Client (Computer which run VPN connection) from server by Remote Desktop Services, VPN Connection disconnects. This happens when my client is Windows Server 2016-2019 and this is not happen on Windows Server 2008.

I've test multiple circumstances to find problem. When I connect VPN by logging on Windows 2016-2019, Only when I try to connect by same user is stable and when trying to connect by another user through Remote Desktop Services VPN connection disconnects.

I made an windows schedule job to connect VPN. Just when run as SYSTEM user everything is good. But when run as another users problem exists.

Thanks in advanced for you help

S. Pirahesh

Remote Desktop
Remote Desktop
A Microsoft app that connects remotely to computers and to virtual apps and desktops.
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  1. Carl Fan 6,836 Reputation points

    Have you checked the event log if some related event error could be found?
    First check if VPN client can ping the remote computer with source VPN address when VPN connected.
    Check whether to configure any policy on VPN Server to deny the remote desktop.
    To eliminate potential influence against VPN connection, please turn off windows firewall of VPN server and client and try it again.
    Hope this helps and please help to accept as Answer if the response is useful.
    Best Regards,

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