When the ITEMS_ON_HOLD_SHELF exception occurs, the "Automatically override for subsequent items?" option only affects the ability to allow the checkout of items on another patron's hold shelf. This option does not carry over the ability (when checked) to “Cancel this hold upon checkout” for all subsequent items, so the hold for the first item gets canceled, but for the subsequent items, the holds get reset. This means staff either have to leave the "Automatically override for subsequent items?" option unchecked to bring up the alert for each item to cancel each hold - or check both upon the first instance, so the alert does not pop up for subsequent items, but then staff would need to cancel the subsequent item holds through the Actions menu.
There is a Circulation setting for “Clear hold when other patron checks out item,” which determines if the “Cancel this hold upon checkout?” option is checked or not (when set to true, it defaults to yes/checked). But when set to true, the same issue occurs where only the first hold is canceled.
Confirming that this is still in Evergreen 3.11.3.