If I manually enter the contact ID into the field that the workflow updates with the contact ID and then try to save it, the duplicate/matching rule flags it appropriately.
Anyone have any wisdom? I'd love any suggestion that would let me keep folks from creating (or at least flag) duplicate records of a custom object based on a match between a contact and another custom object. So far, the only things I can come up with involve a lot of button-hacking auto-population nonsense, and I'd rather not go down that road more frequently than I have to.
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On your field update, do you have the 'reevaluate' checkbox checked?