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@adrian_chmiala as far as I know, it isn't possible to set up custom checklist item due date reminders with butler automation for the moment. What you've set up will actually trigger when a due date is set on the checklist item. What you need is a due date command that is triggered based on when the checklist item is due. You can create custom due date reminders that are based off the card due date, and I believe there are default checklist due date reminders, but no custom checklist due date automations for now. I'd suggest submitting a feature request!