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?

Is the field on the Item Transaction stored? Non-stored fields are sometimes treated as there by workflows (as in sources for Set Field Value actions) and sometimes not (as in saved search conditions).