Enable Multiple Login Sessions in Windows Server – Beginning to End.

You might need to enable multiple login sessions in windows server for many reasons. In my case I wanted to build 1 development machine, and allow multiple developers to work on it without the need to build more servers, without needing to manage and maintain multiple servers.

The road to getting this completely and successfully configured sometimes is lost half way, but here we will work together to enable multiple login sessions in windows server, completely configured, and correctly configured.

I am working on Windows Server 2016, but I believe this also applies to Windows 2012 or 2012 R2, and perhaps even earlier versions.

  1. First thing you need to do is to add the following Roles:

Enable Multiple Login Sessions in Windows Server


2. Focus on the red square items:
    Remote Desktop Licensing and Remote Desktop Session Host

3. After you install them, open the Local Group Policy Editor by running this command:

4. Now navigate to:
   Computer Configuration > Administrative Templates > Windows Components >Remote Desktop Services >    Remote Desktop Session Host > Connections

Enable Multiple Login Sessions in Windows Server

5. Open: Restrict Remote Desktop Services user to a single Remote Desktop Services session

6. Make sure it is Disabled

7. Open: Limit number of connections

8. Make sure it is Enabled, and set the RD Maximum Connections allowed to: 999999.

At this point a lot of people think that they are done, however, this will only work for a period of time, approximately 30 days. Until you actually install licenses, you will keep getting a warning message like this: Remote Desktop licensing mode is not configured.

Enable Multiple Login Sessions in Windows Server

To finish  the configuration properly and enable multiple login sessions in Windows Server, follow the next steps:

9. Open Remote Desktop Licensing Manager, from this path:
C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Administrative Tools\Remote Desktop Services

10. When opened, you can configure it to connect to LOCALHOST, because this is the server we will configure the licenses in.

11. Select the server from the left pane:

Enable Multiple Login Sessions in Windows Server

12. From the two options on the right pane, right click the Windows Server 2016 … and select Install Licenses.

13. In my case, since I am configuring a development server, I can use my MSDN account to get my license pack.

Enable Multiple Login Sessions in Windows Server

14. You should be able to use either one of the two types of licensing. These are what Microsoft calls Retail Licenses, even though they are not meant for production use. You could use Retail licenses for production as well.

15. Once added, it will validate and will allocate the licenses, in my case 50 licenses.

16. You might need to reboot now, in order for all of this to take effect.

17. As you can imagine, you can have other servers point to this one to acquire licenses, instead of having to install licenses again on other servers. I don’t think you can install the same active license on more than 1 server at a time.


Considerations to Enable Multiple Sessions in Windows Server


  • When you enable multiple sessions on Windows Server, you need to keep in mind that each logged in user consumes resources, such as network bandwidth, memory, disk and CPU. This is at a minimum, even if they don’t do anything. Let alone if they actually execute something. So be careful in allowing too many users on the same server, otherwise assign more resources such as CPU and/or memory to the server.
  • Disconnecting from a Server is not the same as Logging off. I am actually surprised how many administrators don’t know this, or simply don’t care and disconnect from a Server without logging off. By disconnecting, the user detaches him/her-self from and RDP connection, but the Profile keeps running, hence consuming the resources still. Ask your people to log off when they are done working on the server (including yourself).
  • A lot of Organizations enforce log off with GPOs by monitoring inactivity time. This is generally hated by developers because they log on a server, and leave their session open during lunch, and come back to continue, leaving all of their development tools open. So, I personally don’t like to enforce this on development machines, but maybe Production?
  • Consider having a centralized server to keep the licenses installed, and each server that makes use of them pointing to it. This way you can use the same pack of licenses.


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