I just ran a test. Installed OBS-HUD to the standard Program Files directory. Added an entry to Task Scheduler. Selected the "Run with highest privileges" checkbox. Manually choosing the Run option on the task starts it correctly with elevated permissions.
Task is set to start automatically on user login. When I restarted, it did not start. I changed the trigger to add a 30 second delay, rebooted, and then it *did* start correctly.
Try adding a startup delay to your scheduled task and see if that gets it to work correctly. Please let me know the results.
View attachment 119556