Automatically. Every time the KDS loads, Sprwt asks Uber for the status of each order that has a courier:

• If Uber reports delivered, the order is set to Finished and leaves the board.
• If Uber reports the delivery was canceled (by Uber or the courier), the order is put back to Ready so you can request another courier or cancel the order.

Staff do not need to press anything for deliveries once the courier is requested. The Uber tracking link and estimated delivery time are shown on the order's page in Customer Orders.