The purpose of this study was to examine personality characteristics of Internet sex offenders who were on federal probation and had presented for mandated psychological evaluations. Offenders convicted of contact offenses were compared to noncontact offenders in regard to demographic characteristics and selected MMPI-2 primary clinical, Restructured Clinical (RC), and Personality Psychopathology Five (PSY-5) scales. A total of 52 male subjects (26 contact and 26 noncontact offenders) were included in this archival study. The results showed no significant differences between groups in regard to basic demographic characteristics. The MMPI-2 scale results tended to be within normal limits and more similarities than differences were observed between the 2 groups. However, noncontact offenders scored significantly higher than contact offenders on Scale 0 (Social Introversion) and on RC2 (Low Positive Emotions). In addition, although the difference on INTR (Introversion/Low Positive Emotionality) was not statistically significant, a clinically meaningful difference was found in which noncontact offenders scored higher than contact offenders. The noncontact Internet sex offenders in the present study showed greater social introversion, shyness, and discomfort in social situations than contact offenders. They also displayed less capacity for positive emotions and more depressive features. It may be that the greater social isolation displayed by noncontact offenders puts them at increased risk for depressive symptoms, though additional research on this possibility is needed. These findings confirm the importance of addressing social relationship patterns, depressive features, and related concerns in the initial assessments of Internet sex offenders. Other findings, clinical implications, study limitations, and suggestions for future research are also discussed.