There has been growing interest in medical-legal partnership (MLP), a model which connects healthcare facilities with legal clinics to help address clients’ civil legal needs (e.g., evictions and child custody matters). More research is needed on best practices for legal needs screening and identification of subpopulations vulnerable to complex legal issues. In this study, we examined client intake and other linked administrative data from the Connecticut Veterans Legal Center which is partnered with the Veterans Affairs Connecticut Healthcare System. We aimed to examine (1) the frequency of accurate client self-reports of legal issues as compared to the legal issue identified by an attorney, (2) the extent to which clients reported repeated past and current legal issues, and (3) associations between clients’ mental health diagnoses and number of self-reported legal issues. Among 73 clients in the sample, 47 (64.4%) had a match between their self-report legal issue and the attorney-identified legal issue and 46 (74.2% of 62 clients who reported past and current issues) had at least one repeated issue. In adjusted Poisson regression models estimating the association between mental health diagnosis and clients’ number of current legal issues, clients with posttraumatic stress disorder (b = 0.32, 95% CI = 0.01, 0.63), and alcohol use disorder (b = 0.45, 95% CI = 0.15, 0.74), reported more current legal issues on average compared to those without these diagnoses. Future research should examine how best to identify and support clients’ legal needs, and how these needs interact with mental health challenges.