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Reboot Task will not work with Servers

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I have a handful of servers that I like to reboot once a week to "refresh" them.

 

I created a Reboot Task. My settings are:  Act as if reboot is ALWAYS needed.

 

I move a server in and it fails. It comes back:  Server does not need a reboot.

 

However, I can right click on the server under All devices, choose reboot and it will reboot.

 

Any suggestions on what I need to do so I can set this up to reboot them automatically?


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