There is a continually growing demand for mental health evaluations and services in both courts and law enforcement agencies. In addition, the use of mental health professionals as expert witnesses continues to extend beyond traditional judicial applications. The question then arises, how do we distinguish between criminal intent, psychiatric illness and immaturity? Can a child be considered not guilty by reason of insanity, guilty but mentally ill, or to have diminished capacity? This Clinical Case Conference examines the conflict regarding the prosecution of children and what it reveals about the negotiation and navigation of legal boundaries in light of advances in our knowledge and understanding of both psychosocial and neuro-development. A number of questions are examined including: can an eight year old boy accused of killing his father be considered criminally culpable? What is the court's approach to juveniles who are accused of homicide? Should a minor be interviewed without counsel present? Should children be afforded the same legal rights as adults? Does an eight year old boy have the capacity to stand trial? Should children be viewed as adults for purposes of legal criminal status?