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Creating a Dynamic Checklist with Custom Objects

We are looking to use custom objects to dynamically create a checklist for students who are missing items. Example (Orientation, Registering for Classes, Health form, etc.). We currently have these checklist items set up as checklist codes with custom objects, with a checklist receive date. This information is passed from our SIS, Banner.

When creating the emails I used the following criteria:

- Has linked contact in custom object checklist code = BILL (Pay Your Bill)

AND has linked contact in custom object receive date is Blank.

This logic should populate the item 'Pay Your Bill' within the checklist email.

The problem I am running into is that if all checklist items have a receive date but one is blank, all checklist items appear in the email instead of just the missing item.

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