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A good job has long been considered a key milestone on the road to desistance after incarceration. In-prison vocational training programs provide individuals with skills and credentials to foster opportunities in middle-skills jobs post-release. Even though vocational training programs are on offer in three-quarters of US prisons, little is known about whether these programs live up to their promise. Drawing on insights from the literature on the labor market experiences of individuals with criminal records, we highlight that vocational training may primarily affect \textit{where} individuals work post-release. This paper then estimates the impact of in-prison vocational training on sector-specific job attainment using an instrumental variable design. We find that vocational training participants are significantly more likely to secure employment in their training sectors after release compared to similarly situated peers. However, these sector-specific employment gains are short-lived, challenging the notion that vocational training leads directly to stable employment in the middle-skills jobs they target. Notably, however, trainees are more likely to remain employed in the second half of the year, and experience significant overall earnings increases during this period. This suggests that rather than securing the steady jobs they received training for, trainees may be leveraging their initial work experience in their sectors of training to transition into more sustainable employment journeys in other sectors.