Abstract: A rules-based expert system is described in which the information relating to health or retirement benefits are stored in the form of statements or clauses relating to financial, medical, or personal characteristics relevant to statue or regulation at issue. The statements, or rules, are stored in a rules engine, or knowledge base in the form of “If X, then Y.” The specific construction of the data declarations relating to retirement and health benefit planning relies on parsing federal, state, and local regulations and statutes regarding Medicare, Medicaid, Social Security, as well as general health insurance and long-term care insurance. The rules are applied to the user characteristics and to data about available policies to identify the policies most likely to be of greatest benefit and least cost to the user.