1. Add new circulation rule “ConfirmCheckoutsCrossingHoldExpiration” 2. You can then enable this rule just for one item type 3. If the checkout matches this rule, and the checkout would be due after the hold’s expiration date, a popup dialog would display. This dialog would have the following options: a) Ignore b) Reduce loan length to the day before the hold’s expiration date c) Cancel checkout Seeking Co-sponsors: http://devs.bywatersolutions.com/projects/datetime-specific-material-reservations/