Background: Court-involved students, such as those in foster care and the juvenile justice system, generally experience high incidences of both acute and chronic trauma, adversely impacting their educational well-being and overall academic trajectory. Utilizing perceptions of teachers and other school staff, this study explores the challenges and needs of school personnel working with this student population. Methods: Participants were school personnel employed at a Midwest, urban, public charter school during the 2012-2013 academic year. Focus groups explored the perceptions of school staff members working with court-involved students to develop a staff training curriculum. Focus groups also were conducted after the training intervention to get feedback from participants and identify remaining challenges. Focus group data were analyzed and results were member-checked with study participants. Results: Findings included 7 major themes (14 subthemes) regarding student behaviors that were challenging for school staff to manage. Themes included trauma-related behaviors, attachment-related behaviors, staff preintervention needs, intervention feedback, and staff postintervention needs. Conclusions: Teachers and school staff can play a role in the educational well-being of court-involved youth. However, they need trauma-specific knowledge and resources to be effective. [This study was funded by Title funds as defined under the Elementary and Secondary Education Act of 1965, provided by the United States Department of Education, Beverly A. Baroni, Principal, Clara B. Ford Academy.]