Remote desktop no longer prompting when both connections are used

Question

We have a Windows Server 2008 R2 Enterprise which we regularly remote desktop into that does not have Terminal Services. It used to give us a prompt when both connections were already in use, giving us the option to boot one of the users. It randomly stopped giving us that dialog one day, now it just gives a generic cannot connect error when both connections are in use. As far as we know nothing changed on the server and we've tried rebooting, any ideas how to get that dialog back?

Answer 1

To enable the multi-instance prompt, please check and change the below Registry value: This should resolve your issue.

HKLM\SYSTEM\CurrentControlSet\Control\Terminal Server\WinStations\RDP-Tcp\MaxInstanceCount

Set 'MaxInstanceCount' to DWORD value of hex 0xffffffff

For any remote connection issue, on several occasions, remote desktop does not correctly enabled in the firewall exception settings for the RDP port (3389). Check whether the port is enabled in inbound and outbound rules (Control Panel > Firewall Settings > Advance Settings). To isolate the issue, please turn off the firewall and, reboot the machine and check.

For proper shutdown, always use the /admin option when starting a remote session using mstsc, that will initiate proper reboot, or use the 'shutdown' command from your laptop to do the reboot

Hope this helps.