The Multi-Context Problems Checklist (MCPC) is a new measure of personality-related problems designed for a young adult population. Previously published problem checklists either have little supporting empirical documentation to support their validity or focus on specific kinds of difficulties in specific contexts (e.g., interpersonal, close relationships). The MCPC is a straightforward and easy-to-use instrument covering 6 domains of functioning, takes about 5 minutes to complete, and is intended for young adults ages 18 to 29. Psychometric data are presented in 3 studies. In Study 1, correlations with self- and observer ratings showed scores on the MCPC to be consensually valid, and associations with measures of well-being and personality provided evidence of construct validity. Study 2 added to these findings by identifying specific personality-related problems associated with each pole of each trait of the five-factor model of personality, demonstrating moderate to high test-retest reliability of problem endorsements, and showing strong associations with measures of psychological distress. Study 3 indicated that the MCPC is sufficiently sensitive to capture more frequent problem reporting among individuals undergoing counseling. Problem-trait associations are related to a broader literature on global personality dimensions and psychosocial outcomes at the individual, interpersonal, and social and institutional levels. The MCPC deserves attention from both researchers and clinicians who are interested in assessing personality-related problems in living.