The present invention is a method for managing funds in anticipation of paying at least two financial obligations, such as an estimated tax payment and a mortgage payment. The due dates and amounts due are determined from customer financial information. During an escrow period leading up to the first obligation due date, amounts of money are transferred on at least two occasions from a customer account into a second account, whereby the combined value of the transferred amounts substantially matches the estimated tax or other amount due for the first obligation. The transfer amounts and/or timing are adjusted so as to maintain sufficient funds in the customer account for paying the other obligations. The transferred money is used to automatically pay the first obligation on or near the due date. In embodiments, the customer can access the money in the second account until the first financial obligation is paid.