Objective: The aim was to evaluate in-office discussions of ADHD and psychiatric comorbidities. Method: Naturally occurring interactions among 11 psychiatrists, 32 patients and their parents were recorded, with a focus on "complicated" patients (i.e., having or suspected to have [greater than or equal to] 1 psychiatric comorbidities and/or learning disabilities in addition to ADHD). Participants were interviewed separately post visit. Transcripts were analyzed using validated sociolinguistic methodologies. Results: Some 62% of patients were male, with an average age of 12.5 years, and 79% had a family history of ADHD. Visits were psychiatrist-driven, focusing on medication management and school performance, leaving management of comorbidities largely unaddressed. Post visit, 78% of parents and psychiatrists disagreed on patients' "most concerning behavior." Parents most often reported concern about aggression and oppositionality. Psychiatrists and parents emphasized different aspects of patients' personality, using deficit- and strength-based models, respectively. Conclusion: Psychiatrists and parents interpreted the relationship between ADHD and comorbidities differently. The significant incidence of misalignment regarding worrisome behaviors warrants further exploration. (Contains 4 tables, 1 figure and 1 note.)