trade in
If I want to purchase a new ipad pro, can i trade in both my current ipad and my macbook pro for one item
MacBook Pro Retina
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I don't know of a way to trade more than one item if you do it at the same time as making an online purchase, but you may want to contact Apple sales support at 1-800-MY-APPLE to verify that.
If you cannot, another option would be to trade one (or both) of the items ahead of time for a gift card and then use that card (or those cards) as partial payment for the new item. See the following to initiate a trade without a purchase: Apple Trade In - Apple