The importance of a cooperative school administrator-school counselor alliance is explored against the backdrop of legal proceedings involving professionals in both disciplines who at different points could have prevented or averted lengthy, energy-draining legal action. Most legal battles involving school administrators and school counselors revolve around child abuse reporting, confidentiality, and advocacy for equitable educational opportunities. An examination of case law, statutes, office of civil rights investigations, and other legal proceedings underscores the implications and consequences of school administrators (e.g., principals and assistant principals) and school counselors neglecting to understand disparate, and often mutual, legal and ethical imperatives. An alliance can afford greater comfort for both educational fields in ambiguous and situational dilemmas that are part of the daily work of school administrators and school counselors. Positive collaboration also can lead to increasing opportunities to develop social capital and better support outcomes for students.