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This feature will not work if Windows Server Backup has reached the state where it cannot further contract the snapshot allocated space and also preserve some of the existing backups. This happens when space required to complete the backup causes the snapshot storage space to become less than 1/8 of the target size. You can change the snapshot storage from here: Volume ==> properties ==> shadow copies ==> settings.
If the Automatic Disk usage management criterions are not satisfied, you can still delete old backups created by Windows Server Backup. For the steps to do this, refer to the next section.
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