We are transitioning to Named User Licensing and have discovered a known issue regarding running scripts on a headless account with a Named User License. In order to keep the license fresh, ArcGIS Pro must be opened once every 15 days or the token will expire and the scripts will stop working. We found a helpful little script by ESRI support that automatically opens and closes Pro for this exact purpose and set it up to run weekly with Windows Task Manger. https://support.esri.com/en-us/knowledge-base/how-to-automate-arcgis-pro-launch-and-shutdown-to-refre-000033675#:~:text=Summary,subprocess%20object%20representing%20ArcGIS%20Pro.
But, here's the question: How do you know the light goes off in the refrigerator when you close the door? Is there some way to confirm that the Named User Token is actually being refreshed before the scripts start failing?