Decisions in student affairs often require the integration of multiple knowledge bases (O'Brien, 2018). Although learning and development have historically been core values of the profession (Evans & Reason, 2001), legal demands on student affairs professionals have grown with increasing responsibility for compliance in areas like Title IX and campus speech policies (Kaplin & Lee, 2014; Lake, 2011). While guidelines for relevant legal training exist (American College Personnel Association & National Association of Student Personnel Administrators [ACPA & NASPA], 2015), student affairs professionals come from a variety of educational and professional backgrounds (Wesaw & Sponsler, 2014). Using a focused reanalysis of data derived from a constructivist grounded theory study of legal reasoning in student affairs, we explored how practitioners think about their own training in the law as well as how they perceive colleagues with advanced legal training (e.g., law degrees, participation in continuing education).