Hi @Max_Dickinson ,
When you check an item which is linked with an another card, you can use this rule :
when an item is checked, find a card with link "{checklistitemname}", and add the red label to the card
When you check an item, but the cardlink is in the attachments , use this rule :
when an item is checked, find the first card linked in the attachments, and add the red label to the card
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