This paper examines risk and liability issues related to school to work (STW) programs. With the passage of the federal School-to-Work Opportunities Act of 1994, the distance between the school and the world of work is diminishing. The Act's requirement that students, schools, and employers become part of an integrated learning process brings the parties together in rather unique and unfamiliar roles. Child labor laws, liability laws and issues, and risk management directly impact operations of STW programs. Vermont and other states have formed statewide STW risk management committees, prepared risk management manuals, and provided multiple training sessions to all involved. STW stakeholders must understand the financial and legal exposures they are subject to when placing students off campus as part of an academic program. Key questions relate to health care insurance, who is responsible for insurance costs, coverage needed for various STW activities, and state and federal legislative mandates. Five major types of insurance are briefly described. Issues that need closer scrutiny and, in some cases, federal action include delineating the employment relationship, defining nonpaid work based learning, producing a national technical assistance guide, workers' compensation and paid work-based learning, student health and safety on the job, a central information source, definitions of insurance coverage, insurance product review and development, and liability in areas other than physical injury. Tables of insurance options for various activities and an STW risk matrix are included. (SV)