Windows remote desktop service running, but not listening on port 3389

What about events in the Windows? Is there anything in Windows Event Manager? Maybe it is some sort of Port conflict inside the Windows. Run the following command - "netstat -an" and share the output. Also, you can change the decimal value of the RDP default port and try to log in.

Take a look at Microsoft forum https://social.technet.microsoft.com/Forums/windowsserver/en-US/c3cfc2df-fc29-4abc-acf1-01797f528333/port-3389-not-listening?forum=winserverTS

There are the problems with some MS driver:

"We opened a case with Microsoft on this issue and we determined that it was related to the following driver being disabled: remote desktop services security filter driver To check whether this enabled or disabled, open device manager and show hidden devices. We were not able to enable it, so we uninstalled it and rebooted. After rebooting we were able to telnet to the server on port 3389, but we were still not able to connect with remote desktop. As a last step, we set remote desktop security layer to “negotiate”. To do this, open the "remote desktop session host configuration" application in administrative tools and edit the properties of “rdp-tcp”. The setting can be found on the general tab. Hope this helps someone!"

This is a bug.

Update:

Microsoft fixed the issue within the update KB4482887 (build 17763.348, released on 2019-03-01). Last time I checked it had to be installed manually and was not available through the server's update feed:

~$ wasu.exe kb4482887.msu

For more info see this thread.

I had the same issue and it was due to "Remote Desktop Services UserMode Port Redirector" service being disabled. I enabled it and restarted both services and it started listening on 3389