My systems are showing pending restart because I am pushing a few months worth of patches. Knowing this may take a few reboots how can I accomplish this in one action instead of scheduling several separate actions?
It does seem as though Microsoft requires reboots more frequently than before with their patches. That being said, @mwolff lays out a process that seems to be working well in their environment by rebooting prior to the maintenance window, then executing up to 3 reboots during the window/baseline:
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