best response confirmed by Ben Owens (Contributor)

Hi @Ben Owens 


Q1: It's like a queue, the 1st activated device will drop off the list when the 6th one is activated. The user may not see the device become unlicensed as the device may not have checked into Microsoft 365. The device will poll every 30 days. Once the device drops the enterprise license, it should switch back pro.


Q2: You can use the PowerShell command get-windowsedition and it will report enterprise or pro depending on the activated license. If you are activating via Office365, it should handle the changed when you add or remove a license. Local installs would use something like KMS, so you can switch the version with slmgr.vbs.


Q3: not sure on the process exe that runs the tasks. Its part of the Windows activation process. To troubleshoot this, use the standard activation steps. 

1. Is the existing license supporting the update to enterprise and is it activated.

2. Is the activation via KMS, then check DNS, SLMGR.VBS commands etc

3. Is the activation via AzureAD, then check DNS,  dsregcmd /status etc


All the information is in the link