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NSC | Create a Special Order Purchase Order for a NEW Item Line in a Sales Order
Scenario 1: There is a Purchase Order already created for the Sales Order
The standard behavior of the system is that once the Sales Order is saved and a Purchase Order is already created, you will not be able to create a new Purchase Order for that Sales Order anymore. You would need to create a new Sales Order to have a Purchase Order created for that item again.
This is currently tracked in Enhancement # 156993 - Ability to automatically generate a purchase order number for an added line Item when editing a saved sales order wherein a purchase order number already created