The present disclosure involves systems, software, and computer implemented methods for sending payment requests to one or more persons or entities based on images in which the persons or entities appear. In one example, operations may include identifying a first image associated with a payment request, the identified first image including one or more identifiers of persons, as well as identifying a second image associated with a bill, the bill including one or more line items, each line item associated with a cost. In response to a request to initiate a bill payment split, the bill is presented where at least a portion of the line items are selectable. A selection of at least one line item is received, and a selection of a particular person from the one or more identifiers of persons to be associated with the at least one line items is received. The at least one selected line item is assigned to the selected particular person.