In some examples, a payment processing system may receive identity information identifying a buyer interested in purchasing an item from a first merchant. The system may determine, based on the identity information and item information, that the buyer is eligible for financing the purchase of the item. The system may generate a customized financing offer for the buyer to finance at least a portion of the purchase price of the item. For example, the customized financing offer may include financing terms and may be based on previous financing activity of the buyer with one or more merchants associated with the payment processing system, and/or previous financing activity associated with one or more buyers that have financed the item from one or more merchants. The payment processing system may transmit the customized financing offer to cause a user interface to present the customized financing offer to the buyer.