Adolescent patients with obesity are at significant risk of developing an eating disorder (ED), yet due to their higher weight status their symptoms often go unrecognized and untreated. Although not widely known, individuals with a weight history in the overweight (BMI-for-age ≥85th percentile but <95th percentile, as defined by Centers for Disease Control and Prevention growth charts) or obese (BMI-for-age ≥95th percentile, as defined by the Centers for Disease Control and Prevention growth charts) range, represent a substantial portion of adolescents presenting for ED treatment. Given research that suggests that early intervention promotes the best chance of recovery, it is imperative that these children’s and adolescents’ ED symptoms are identified and that intervention is offered before the disease progresses. This report presents 2 examples of EDs that developed in the context of obese adolescents’ efforts to reduce their weight. Each case shows specific challenges in the identification of ED behaviors in adolescents with this weight history and the corresponding delay such teenagers experience accessing appropriate treatment.