The relationship of insight with the social behaviors of outpatients with severe mental illness (SMI) was investigated. Participants’ engaged in two social interactions (i.e., stigmatizing and nonstigmatizing), each with a different research confederate. The participant’s behavior was later coded for the presence of various self-presentation and social skill variables. Results indicated that greater insight was associated with better overall social skill, less observed strangeness, and greater self-disclosure of one’s mental illness. Furthermore, the three measures of insight, one based on self-report and two interview-based, were all highly intercorrelated, suggesting that they are measuring a similar construct. Finally, consistent with previous research in the area, greater insight was associated with less severe psychiatric symptoms. Implications of these findings for future research are discussed.