Purpose: This article outlines findings from a sample of 137 vocational rehabilitation counselors regarding their stigmatizing attitudes, burnout levels, work experience, caseload composition, and working alliance with clients who have a range of disabilities and a criminal history. Method: Electronic surveys were sent to vocational rehabilitation counselors in 3 states who met the following criteria: counselors with a master's degree, counselors with diverse and active caseloads, and counselors from geographically diverse states. Data were analyzed using 2-tailed correlation analysis and subsequent regression analysis. Results: VR counselors with more ex-offenders on their caseloads did not have higher stigma or burnout but, surprisingly, did have stronger working alliance. Conclusion: Findings support further research to confirm if specialized caseloads comprised of clients with criminal histories enhance working alliances among VR counselors.