This chapter reviews recent and emerging legal concerns in the increasingly varied and complex areas of group insurance, bond issuance, and annuity programs, each of which will impinge significantly on school operations in the years ahead, thus involving more staff and administrative time. Group insurance has developed into a major bargaining concern on account of the skyrocketing costs of health insurance. Accordingly, the Health Maintenance Organization (HMO) has arisen as a substitute for group insurance, but no employer is required to pay more as a result of HMO provision than is required by a prevailing health benefits contract. Other issues in group insurance include double coverage of married employees, taxable fringe benefits, and tax deferral strategies including board-paid teacher retirement, tax sheltered annuities, and deferred compensaion plans. The potential problems facing school districts as a result of the Tax Equity and Fiscal Responsibility Act of 1982 are discussed. This modification in the law, requiring bond issuance in registered form, will likely increase the bid price of a bond issue, the cost of printing bonds, and the transfer costs, while proposed modification in existing arbitrage rule will substantially reduce legal borrowing. Clearly, the costs in the area of group insurance and bond issuance are rising. (TE)