When an item on the hold shelf for one patron is checked out to another patron, staff are presented with an option to check out to current patron and cancel the hold and override for subsequent items. The cancel the hold only works for the first item checked out if override for subsequent items is checked. If there is more than one item on the hold shelf to check out to another patron, the hold(s) are not cancelled. The Automatically override for subsequent items does not work. Staff may not know the subsequent holds were not cancelled and if they do realize, it is extra steps to cancel the holds.
https://bugs.launchpad.net/evergreen/+bug/1986945
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