How to have more than two simultaneous RDP sessions to my Windows Server 2019 instance ?

Hi,

I understand that you require more information on enabling more than 2 RDP connections on your instance.

1. Multiple Concurrent RDP Users:

By default, Windows will allow for up to 2 Remote Desktop Admin connections at a time, in all editions of Windows server. In order to allow more users (for example. 5 users logging in at the same time), you must install the Remote Desktop Session Host Role, to allow for more than two concurrent connections. Without this role, you will be limited to only two concurrent sessions to your Windows server at a time.

a) You can install the Remote Desktop Services Session Host and RDS Licensing role to allow for more than two sessions using the steps outlined here [1], or simply run the Powershell commands below as Administrator from your Windows Instance:

	PS:\> Import-Module ServerManager
	PS:\> Add-WindowsFeature RDS-RD-Server
	PS:\> Add-WindowsFeature RDS-Licensing

Once these roles are installed, you will be allowed 120 days grace period to get a license and once this period expires, a Remote Desktop Client Access License is required [2]. If a license has not been set up, you may encounter an error when attempting to RDP thereafter. I will explain more about the Client Access Licenses next.

b) You can then setup local user accounts for each user as shown in the third party article here: https://computingforgeeks.com/adding-local-user-account-to-windows-server-2019/
d) Also ensure that you've added these users' source IPs to the RDP 3389 Inbound Rules on the Security Group of the Instance.

Regarding Client Access Licenses (CALs):

There are 2 types of CALs: User CALs and Device CALs. User CALs: Are assigned to a user’s properties within Active Directory (i.e Per user). Device CALs: Are physically assigned to each client device that is marked within the registry (i.e Per device). I would like to also share the documentation for Remote Desktop Licensing Demystified [3] which explains CALs differences and uses for when needing to allow concurrent users to connect to your Windows server.

RDP CAL licenses and AWS:

AWS does not sell these Client Access Licenses (CALs) and as mentioned here [4], if additional Remote Desktop Services licenses are needed, Remote Desktop user CALs should be purchased from Microsoft or a Microsoft license reseller. For a list of Microsoft resellers, please refer to reference [5].

RD Licensing Server:

If you are planning to continue using more than 2 concurrent users after the grace period expires, and you've purchased your CAL licenses from an MS reseller. You will need to activate the RDS licensing server and install the CAL licenses received. After activating the RD Licensing Server and installing the CALs, this will also need to be set on GPO. For screenshots and reference of the above steps, please see MS article at [6] at 'Configure licensing for an RDS deployment that includes only the RD Session Host role and the RD Licensing role'. You may also reference the video at [7].

Please Note: CALs and system administration for the setup is something that AWS generally does not provide support for, as Microsoft will have more visibility into their product and agreement with you on these licenses your best solution for further inquiries related to that, will be to contact MS Clearinghouse to discuss your license requirements [8].

I've attached a file with steps on how to Install RDS and RDS Licensing Roles using an example Windows Server 2016 in the attachment to this case.

I hope this helps

Resources:-

[1] Activating Remote Desktop License Server: https://docs.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-activate-license-server
[2] Licensing Remote Desktop Services: https://docs.microsoft.com/en-us/windows-server/remote/remote-desktop-services/rds-client-access-license
[3] Remote Desktop Licensing Demystified https://social.technet.microsoft.com/wiki/contents/articles/21180.remote-desktop-licensing-demystified.aspx
[4] Amazon Web Services and Microsoft FAQs: How can I obtain additional Remote Desktop Services licenses? https://aws.amazon.com/windows/faq/#remotedesktop
[5] Resellers for Microsoft: https://www.microsoft.com/en-ie/p/windows-server-remote-desktop-services-cal/dg7gmgf0dvsv?cid=msft_web_collection
https://www.microsoft.com/en-us/licensing/how-to-buy/how-to-buy
[6] Configure licensing for an RDS deployment that includes only the RD Session Host role and the RD Licensing role: https://docs.microsoft.com/en-us/troubleshoot/windows-server/remote/cannot-connect-rds-no-license-server
[7] How to Install Client Access License (CAL) on Windows Server 2016 https://www.youtube.com/watch?v=b7X7utP2zcU
[8] https://www.microsoft.com/en-us/licensing/existing-customer/activation-centers