Overview

A Windows Server 2022 Remote Desktop Session Host (RDSH) was experiencing a recurring issue where users received Remote Desktop licensing warnings and were forcibly disconnected approximately 60 minutes after login.

During troubleshooting, it was discovered that:

• The affected server was running Windows Server 2022.
• The Remote Desktop Session Host role was installed.
• The RD Licensing Server was running Windows Server 2019.
• The Licensing Server was issuing only Temporary Per-Device RDS CALs.
• Installed RDS CALs were Windows Server 2019 Per Device CALs.
• Users were disconnected after 60 minutes with licensing-related messages.

The root cause was determined to be a Remote Desktop Services license version mismatch.

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Symptoms

Users connecting to the Session Host received warnings similar to:

Remote Desktop License Issue

There is a problem with your Remote Desktop license,
and your session will be disconnected in 60 minutes.

Shortly before disconnect:

You've been connected for the maximum amount of time
allowed for users with Remote Desktop license issues.

Finally:

The remote session was ended because the total logon
time limit was reached.

Environment

RD Session Host

Server Name: core365-rds-cal

Operating System: Windows Server 2022

Role: Remote Desktop Session Host

Verification:

Get-WindowsFeature RDS-RD-Server

Output:

[X] Remote Desktop Session Host
Installed

RD Licensing Server

Operating System: Windows Server 2019
Role: Remote Desktop Licensing Server
Installed CALs: Windows Server 2019 RDS Per Device CALs

Investigation

Confirming Session Host Configuration

The Session Host role was confirmed to be installed:

Get-WindowsFeature RDS-RD-Server

Because the server is acting as an RDS Session Host, Microsoft requires valid RDS licensing for users or devices connecting to it. [learn.microsoft.com]

Checking Licensing Configuration

Running:

Get-RDLicenseConfiguration

returned:

A Remote Desktop Services deployment does not exist

This result is expected when the server is not part of a full RDS deployment managed through RD Connection Broker and does not necessarily indicate a fault. [learn.microsoft.com]

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Examining License Server Activity

The critical clue came from the RD Licensing Server.

The affected Session Host/device was visible within the Licensing Manager but was assigned:

Temporary RDS Per Device CAL

instead of a permanent license.

According to Microsoft, temporary licenses are commonly issued during the initial licensing process, but a valid permanent RDS CAL must eventually be available and assigned. [learn.microsoft.com]

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Understanding RDS CAL Version Compatibility

Microsoft Remote Desktop Services licensing follows strict version compatibility rules.

Important Rule

RDS CALs are:

Backward Compatible

but are not Forward Compatible. [learn.microsoft.com], [learn.microsoft.com]

That means:

Microsoft requires a Windows Server 2022 RD Session Host to be licensed using Windows Server 2022 RDS CALs (or newer). Windows Server 2019 RDS CALs cannot permanently license a Windows Server 2022 Session Host. [learn.microsoft.com], [learn.microsoft.com]

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Can a Windows Server 2019 RD License Server Host Windows Server 2022 CALs?

Yes

This is a common point of confusion.

The operating system of the Licensing Server and the version of the installed CALs are two separate things.

Supported Configuration

RD Licensing Server OS:
Windows Server 2019

Installed CALs:
Windows Server 2022 RDS CALs

Session Host:
Windows Server 2022

This configuration is supported. Microsoft recommends keeping licensing infrastructure current, but a Windows Server 2019 Licensing Server can issue newer CAL packs when properly installed and activated. [learn.microsoft.com], [learn.microsoft.com]

Therefore:

✅ Windows Server 2019 Licensing Server

✅ Windows Server 2022 RDS CAL Pack

✅ Windows Server 2022 Session Host

is a valid deployment.

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Why Temporary CALs Were Being Issued

The licensing process looked like this:

Windows Server 2019 RDS Per Device

The Session Host successfully contacted the Licensing Server.

Because communication was working:

✅ DNS was working.

✅ Network connectivity was working.

✅ Group Policy was likely working.

✅ License Server discovery was working.

However:

❌ No compatible Windows Server 2022 CALs existed.

As a result:

This behavior is consistent with Microsoft’s documented RDS licensing enforcement mechanisms. [learn.microsoft.com]

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Verifying the Issue

Administrators can use the following tools.

Check Installed Session Host Role

Get-WindowsFeature RDS-RD-Server

Generate Group Policy Results

gpresult /h C:\Temp\gp.html

Verify:

Computer Configuration
  Administrative Templates
    Windows Components
      Remote Desktop Services
        Remote Desktop Session Host
          Licensing

Review:

Use the specified Remote Desktop license servers

Set the Remote Desktop licensing mode

Open RD Licensing Diagnoser

Server Manager
→ Tools
→ Remote Desktop Services
→ RD Licensing Diagnoser

The Diagnoser often identifies:

License version mismatch
No licenses available
License server unavailable
Licensing mode not configured

Review Installed CAL Packs

Open:

Remote Desktop Licensing Manager

Check whether the license pack displays:

Windows Server 2019 RDS Per Device CAL

or

Windows Server 2022 RDS Per Device CAL

Resolution

Recommended Solution

Purchase and install:

Windows Server 2022 RDS Per Device CALs

on the existing Windows Server 2019 Licensing Server.

Installation Process

After installation:

gpupdate /force

Then reboot the Session Host.

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Expected Result After Fix

The Licensing Server should show:

Issued Per Device License

instead of:

Temporary Per Device License

Users should:

✅ Receive permanent RDS licenses

✅ No longer receive licensing warnings

✅ No longer be disconnected after 60 minutes

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Conclusion

The issue was not caused by network connectivity, DNS, Group Policy, or a malfunctioning License Server.

The root cause was a licensing mismatch:

Although the Windows Server 2019 Licensing Server could communicate with the Session Host and issue temporary licenses, it could not provide a permanent license because Windows Server 2019 RDS CALs are not valid for a Windows Server 2022 Session Host. Microsoft requires matching or newer RDS CAL versions for Session Hosts. Installing Windows Server 2022 RDS CALs on the existing Windows Server 2019 Licensing Server resolves the issue and removes the 60-minute session restriction. [learn.microsoft.com], [learn.microsoft.com]

References

• Microsoft Learn – License Remote Desktop Services with Client Access Licenses (CALs) – https://learn.microsoft.com/windows-server/remote/remote-desktop-services/rds-client-access-license [learn.microsoft.com]
• Microsoft Learn – Supported Configurations for Remote Desktop Services – https://learn.microsoft.com/windows-server/remote/remote-desktop-services/rds-supported-config [learn.microsoft.com]