This research investigates the association between judge's and target's personality and personality judgment accuracy. Participants (N = 466) completed personality testing, a social interaction task with a partner, and then rated their partner's personality. Participants initially interacted together for 3 min and then in 1 of 3 interaction conditions (interpersonal closeness, competition, cooperation) for 45 min. Personality judgment accuracy was quantified by the convergence between self-reported and rater-reported personality at each time point. We evaluated the association between information quantity (i.e., time), information quality (i.e., social context), and personality on accuracy. Results indicate a) accuracy improved over time, b) participants in the interpersonal closeness condition were most accurate, and c) judge's agreeableness was positively associated and target's extraversion was negatively associated with accuracy. Findings indicate information quantity and quality influence how personality-relevant information is acquired from other people and some personality traits are associated with personality judgment accuracy.