Systems and methods are disclosed for automated identification and processing of qualifying expenses for tax-advantaged accounts and automated initiation of related account transactions for automated management of those tax-advantaged accounts. In part, the disclosed embodiments: identify expenditures which are eligible for tax-advantaged payment, withdrawal or reimbursement from a limited-purpose tax-advantaged account; store records with relevant details of expenditures to demonstrate eligibility for favorable tax treatment; calculate the amount of and executing contributions to limited-purpose tax-advantaged accounts as a function of account holder preferences, statutory limits and prospective or prior qualifying expenditures from other accounts; identifying withdrawals from limited-purpose tax-advantaged accounts which do not qualify for the tax advantage and restoring those monies to the account or offsetting them against amounts otherwise reimbursable from the account; and automatically reimbursing the account holder from his limited-purpose tax-advantaged account as a function of account holder preferences, information about qualifying expenditures made from another account or contributions to the account.