Premorbid obesity is an identified risk factor for eating disorder (ED) development among adolescent males. However, pervasive gender- and weight-related biases about ED inhibit timely diagnosis and treatment among this demographic. This study examined the psychological and medical characteristics of three adolescent males with premorbid obesity who were not diagnosed with atypical anorexia nervosa (AAN) until medical sequelae of malnutrition warranted emergent hospitalization. Factors associated with diagnostic delays among these cases were identified to facilitate increased awareness of this at-risk demographic.