An automated account management system provides a user with the ability to establish rules that dictate how the account management system is to manage the user's accounts. Once the user specifies a set of rules, the system automatically manages multiple accounts across multiple financial institutions in accordance with the user-defined rules. Other features, such as an on-line bill payment system, a money transfer system, and a retirement planning system, may be integrated within the automated account management system to provide the user with even greater control over his or her financial assets.