Abstract: Apparatus and methods for improving online bill payment processes are provided. Online bill payment typically involves a paying party (“payor”), an intermediary (such as a bank, a billpay service or a billpay network) and a payee. In some embodiments, the apparatus and methods may provide optional file attachments that may be communicated from a payor (initiator) to a payee (recipient). Such attachments might include a signed contract for products or services, a payment stub with descriptive details of the payment, a photo of an item being purchased, or any other document that the payor wishes to send in connection with the payment transaction.