Abstract: Techniques are described for using loyalty program points and other non-monetary loyalty rewards from a first organization in a monetary manner at a distinct second organization, such as to acquire an item from a merchant at a cost that is reduced by a monetary amount based on the loyalty reward used. In some situations, the first organization programmatically interacts with a merchant to cause a gift certificate to be dynamically created for the merchant in an appropriate monetary amount, and later applies the gift certificate to reduce the cost of the item acquisition. In addition, in some situations such acquiring of items by a user from a merchant is performed based on interactions between the user and the merchant that are performed so as to appear to the user to be with the first organization and such that subsequent interactions continue between the user and the first organization.