Are you able to see the task created in the scheduled task? And what is the trigger for this scheduled task, only at startup or at startup and every 5 minutes there after. If you are running this task only at startup, it will not run because the startup phase has already passed but there is an option to add a delay which delays the task execution by specified time after startup I believe.
Also as far as I remember scheduled tasks persist after sysprep but I will need to double check this. I would recommend creating a support case for investigation.
Thank you for sharing the details. I will find some time to test it. However, syncing every 2 minutes doesn't seem to be a good idea if the files are big. It can take some time to upload/download the file between S3 and the fleet instance. If you don't configure the schedule task correctly, there may be to many tasks running in parallel which may cause performance issues. As for the case that you opened, I was not able to find it. Please ask the engineer owning the case to contact me by sharing this repost article on the case and I will work with him internally to find the solution.
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