RDP Problem since recent update (March 2020 Commulative Update?)

Copper Contributor

We manage a group of servers. To access these servers we first RDP into a server that has access to all of the other servers. From this first server we used to RDP into other servers.
Now since a few days this second RDP session stopped working, hanging the RDP client after authenticating to the second server.

Client: Windows 10 (Up to date on Windows Updates)
Server(s): Windows 2012 R2  (Up to date on Windows Updates)
So Client->RDP #1 to Stepup server->RDP #2 to server to manage. RDP client for #2 hangs.
We found out that: RDP-ing to server to manage works fine from Stepup server if we are native on the Stepup server (like via VM-Ware Console).
We found out that: When the RDP client hangs on session 2 and we abruptly disconnect RDP #1 and Reconnect #1, RDP#2 continues and operates normally.
We found out that: RDP-ing from an older (not updated) workstation to #1 and then to #2 works just fine.
RDP session #1 crosses a AD Domain barrier (connecting to an other domain with no relation to the Client domain).
RDP session #2 is within the same (target) AD domain.
So, one of the last Windows updates  introduced a problem for RDP-in-RDP.
Does anyone have a clue on what's going on? Eventlogs on Clients and Servers are 'clean', no events we can search for.

Erik Tamminga
1 Reply



Have you tried not connecting Printers / Clipboard / Smart Cards in your mstsc settings. 


Had an issue like this a few months ago, connecting from a jumpbox to legacy Windows 2012 R2 servers and it was the Smart Cards or Windows Hello option.   Customer had Entrust MFA at the time.