One barrier to medication adherence in pediatric populations is difficulty swallowing pills. Some children may not have prerequisite skills for pill swallowing, while others may have developed conditioned anxiety from repeated negative experiences. Eight children with attention deficit hyperactivity disorder or autistic disorder participated in behavioral training to increase cooperation with pill swallowing. A pill-swallowing protocol was utilized during practice sessions with placebo "pills" of increasing size to implement systematic desensitization. Seven of the 8 children swallowed medication with a therapist. Six of the 8 children maintained treatment gains over time. Interventions used to succeed with these children are presented along with methods to reduce conditioned behavioral distress.