I have a Workflow running on Item Fulfillments with a condition of Customer:Email Transactions = T And when I test the workflow and add logging, it is showing that the Customer:Email Transactions is F even though, when I open the Customer, that checkbox is 100% checked. Possibly related.... on Sales Orders, the Customer field is a link to the Customer record, but on the Item Fulfillments, it's just a text field.... is it possible that the Workflow isn't actually checking the Customer:Email Transaction field since the Customer field isn't acting as a linked field?

I don't believe the Customer field is available to Item Fulfillments. Try using the Entity Join.