Why isn't the 'Start a Program on Connection' Group Policy launching an app (Calculator) on RDP login for local users in Windows Server 2022?

Question

Hello everyone,

I'm working on a Windows Server 2022 setup where I need a specific program (Calculator) to start automatically when local users log in via RDP. I've configured the 'Start a program on connection' setting in Local Group Policy (gpedit.msc) under:

I set the program path to C:\Windows\System32\calc.exe. I confirmed with RSOP that the policy is applied, but when users log in via RDP, they only see the desktop; Calculator doesn't start as expected.

Here's what I've tried so far:

1. Verified the program path and tested with other apps (e.g., Notepad).
2. Ran gpupdate /force to ensure policy is updated.
3. Used Task Scheduler to trigger Calculator on login for the user (didn’t work).
4. Made sure users are in the Remote Desktop Users group.

Is there something I'm missing about how the Start a program on connection policy works on Windows Server 2022, or could there be a compatibility issue with launching Calculator? Any help would be greatly appreciated!

PS: this works fine on windows server 2012, also the setup also works fine with active directory domain users.

Answer 1

Hello,

Please review the instructions in this policy carefully to ensure you don’t miss any details on the configuration. I will highlight key points in bold:

Configures Remote Desktop Services to run a specified program automatically upon connection. (You need to install the necessary RDS roles to run this function)

By default, Remote Desktop Services sessions provide access to the full Windows desktop, unless otherwise specified with this setting, by the server administrator, or by the user in configuring the client connection. Enabling this setting overrides the Start Program settings set by the server administrator or user. The Start menu and Windows Desktop are not displayed, and when the user exits the program the session is automatically logged off.

To use this setting, in Program path and file name, type the fully qualified path and file name of the executable file to be run when the user logs on. If necessary, in Working Directory, type the fully qualified path to the starting directory for the program. If you leave Working Directory blank, the program runs with its default working directory. If the specified program path, file name, or working directory is not the name of a valid directory, the RD Session Host server connection fails with an error message.

If the status is set to Enabled, Remote Desktop Services sessions automatically run the specified program and use the specified Working Directory (or the program default directory, if Working Directory is not specified) as the working directory for the program.

If the status is set to Disabled or Not Configured, Remote Desktop Services sessions start with the full desktop, unless the server administrator or user specify otherwise. (See Computer Configuration\Administrative Templates\System\Logon\Run these programs at user logon setting.)

This setting appears in both Computer Configuration and User Configuration. If both settings are configured, the Computer Configuration setting overrides.

Also, the Always show desktop on connection policy setting will take precedence over the Start a program on connection policy setting.

I hope this information helps.

Best regards,

Karlie Weng

Answer 2

Hello Karlie,

Thank you for your response it was very helpful , after all the problem was with the conflicting policies with computer configuration , so i made changes to both of them

Best Regards.