The use of psychoactive medications to augment behavioral and psychosocial interventions in schools has significantly increased within the last few decades. Yet, advising, administrating, and supervising the dispensation of medication (including psychostimulants and psychoactive substances) tend to be some of the most risky tasks of school administrators and personnel. Medication administration is not only an increasing source of civil and administrative liability for school districts, but may lead to legal questions for school counselors, psychologists, and social workers. In response to growing concerns, this article provides guidelines necessary for safe medication administration and monitoring in the school setting. Federal, state, and district guidelines are reviewed. Possible implications for school and district policy makers, principals, teachers, school nurses, school psychologists, social workers, counselors, and parents are outlined.