The Individuals with Disabilities Education Act (1997) requires identification of emotional disturbance by special education criteria. It also requires that emotional disturbance be distinguished from social maladjustment. In some cases, a thorough evaluation of the child's character pathology can aid in this determination. While methods such as the Rorschach, BASC, and MMPI-A are useful in understanding behavior and personality, psychopathy assessment may be particularly useful for organizing opinions in this matter. In this article we discuss the relevance of psychopathy's two-factor structure in formulating a schema for making the differentiation between emotional disturbance and social maladjustment and review methods for gathering information about this troublesome aspect of character pathology. © 2004 Wiley Periodicals, Inc. Psychol Schs 41: 849–860, 2004.