Understanding MacOS Alerts

The alerts from JumpCloud begin once the device detects that it has an update available. Every five hours–twice per average working day–the alert window will launch and prompt the user to update the operating system.

When less than 72 hours remain in the deadline, the alert will increase in frequency from twice per working day to 6 times per working day, every 100 minutes. When less than 24 hours remain in the deadline, the alert will increase in frequency again from every 100 minutes to every 10 minutes.

When the deadline has elapsed, and the system is still not updated, the alerts will continue every 10 minutes, but the window can no longer be closed, will re-center on the screen every 10 minutes, and you cannot quit the app from the UI. If the user discovers the process and terminates it through the command line, it will regenerate.

Alerting Behavior Differences When Major OS Updates Are Available
There are alerting differences for the notifications presented to end users via this policy based on the major OS version a device is running. 

• Update Notification When Running the Latest MacOS Version (MacOS Ventura)
  When a device is running the latest macOS major OS version, the notification for a minor version update drives users to update their devices using the native flow via Apple’s System Preferences > Software Update.
  The dialog in System Preferences that is opened by clicking Update Device will only show the available patches for the system. It shows new versions of the operating system that are already approved, and thus, eligible for update. Follow the steps onscreen to update your device.
  
  When users are within a few days of the deadline for updating the device, they must click I understand to get the Close button to appear. As the IT Admin, you configure the deadline date in the Automatic MacOS Updates policy. After the deadline date passes, users must click Update Device. 
• Update Notification When Major MacOS Update Are Available (MacOS Monterey or Big Sur)
  When a device is not running the latest macOS major version, the notifications presented to end users provide additional information to drive them to update to the latest version of their supported operating system.
  
  The dialog in System Preferences that opens when users click Update Device displays the macOS major version update, as well as instructions for More Info. This notification drives end users to click More Info to learn how to install the required update.
  
  For example, a device that is not running the latest macOS version that is available for installation after clicking More Info can view details in Software Update in Apple’s System Preferences.