Comment 1 for bug 1909586

After looking at this again, it's not that the "Keep history of holds" feature does not work, it does. Holds that you have checked-out or cancelled are removed from the list, if the option is unselected.

The issue may be that your current hold's are displayed in the history list regardless of the setting. The expected behavior would be that the list be empty, if the option is not selected. This is the behavior of the circ history list.