@David Moon , Thanks for posting in Q&A.
Based on my understanding, when the device come online on Dec 1st, the update download automatically and then install during Automatic Maintenance when the device isn't in use or running on battery power. So if the device is online after active hours on Dec 1st. and is not in use It will install the update at that time. Then it will come to restart pending. When restart is required, users are prompted to restart. If the user don't restart, when the pending restart time 2 days is reached, the device will try to restart. The time can be on Dec 3th .(The grace period countdown starts from the time of the pending restart.)
If the device is offline after active hour on Dec 1st or the device is in use, the device will automatically install after 2 days, on Dec 3th. Because the deadline of quality updates, countdown starts from the time the update is offered (not downloaded or installed). After the installation, the device will go into pending restart, and will be forced to restart after 2 days.
Meanwhile, there's another setting "Auto reboot before deadline", if it is set Yes, then the device has installed updates and is outside of active hours, it might attempt an automatic restart before the deadline. If it is set No, devices will delay automatically restarting until both the deadline and grace period have expired, even if applicable updates are already installed and pending a restart.
Here are some articles for the reference:
https://learn.microsoft.com/en-us/mem/intune/protect/windows-update-settings
https://learn.microsoft.com/en-us/windows/deployment/update/wufb-compliancedeadlines
https://learn.microsoft.com/en-us/windows/client-management/mdm/policy-csp-update#update-configuredeadlinenoautoreboot
Hope it can help.
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