Objectives <p>Recidivism remains a significant challenge for the criminal justice system, and employment is a known protective factor against recidivism. However, only about 25% of the more than 600,000 individuals released from state and federal prisons each year find employment within 12 months. This underscores the need for effective vocational training programs to enhance employability. <i>Virtual Reality Job Interview Training</i> (<i>VR-JIT</i>) is an evidence-based practice shown to improve interview skills and employment outcomes for returning citizens when integrated into prison-based programming. This study reports a mixed methods implementation processes evaluation of <i>VR-JIT</i> within two trades-focused prison employment readiness programs. </p> Methods <p>Instructors (<i>n</i> = 4) and program administrators (<i>n</i> = 2) completed surveys and semi-structured interviews to report on <i>VR-JIT</i>’s initial implementation process outcomes (e.g., feasibility, appropriateness, acceptability) and barriers and facilitators of delivery. Residents (<i>n</i> = 56) completed post-intervention surveys assessing usability and acceptability. Qualitative data were analyzed using the Consolidated Framework for Implementation Research (CFIR) and thematic analysis. </p> Results <p>Staff reported <i>VR-JIT</i> as highly acceptable, appropriate, and feasible to deliver with high fidelity. Residents rated the intervention as highly usable and acceptable. Key facilitators included realism of the simulation, opportunities for repetitive practice opportunities, and comprehensive training and support. Structural barriers, such as schedule interruptions and limited resources (e.g., staffing), posed challenges to sustained delivery. </p> Conclusion <p>Findings inform implementation strategies for technology-based employment interventions in correctional settings and advance implementation science in prison-based reentry programming.</p>