Educational leaders' experiences with legal issues remain relatively unknown. Using an electronic survey, this study explored educational leaders' (N = 441) experiences with legal issues and with perceived levels of legal preparedness. Results revealed that years of experience and ethics training courses variables were statistically significant with perceived levels of legal preparedness. The legal issues with the highest frequency reported by educational leaders included suspected child abuse, reports of bullying/harassment, and whether a student poses a danger to other students. Implications for educational leaders and educational training programs are provided.