This dissertation is a collection of three essays. In the first essay, I ask whether jail-based immigration enforcement leads to the profiling of Hispanics by municipal police. I leverage a natural experiment to examine the effects of 287(g) jail partnerships on traffic stops and arrests by municipal police in North Carolina in the late 2000s. I find that stops of Hispanic drivers fell in the wake of 287(g) agreements, and show that this fall was driven by changes in Hispanic road use. While I cannot unambiguously disentangle police and driver behavior, I find no evidence that municipal police officers increased pretextual stops and arrests of Hispanic drivers. Despite this, the signing of 287(g) agreements appears to have prompted Hispanic out-migration and changes in driving behavior, adding to a growing body of evidence on the ripple effects of local-federal immigration enforcement partnerships. The second essay examines the suitability of the Dutch Prison Climate Questionnaire (PCQ) for use in the USA by assessing its psychometric properties using survey data from Pennsylvania. Prison climate surveys are uniquely positioned to identify how the quality of prison life differs both within and between institutions. A comparison of psychometric results between the Netherlands and the USA shows several striking similarities between the two countries, pointing to areas where the factor structure of the survey might be improved. The essay concludes that while the PCQ shows potential for standalone use in the USA, further work would be required to use the tool in explicitly comparative research. In the final essay, I explore the impact of prison-based vocational training programs on labor market outcomes after individuals are released from prison. Using data from one East Coast state, I exploit a natural experiment to estimate the impact of vocational training on sector-specific job attainment. I find that vocational training participants are much more likely to work in their sectors of training compared to similarly situated individuals and earn more in those sectors than their peers. The evidence that participants are more likely to work overall is much weaker - suggesting that vocational training is changing where individuals find work, more so than whether they find work. The significance of these findings rests on the fact that prison-based vocational training programming can successfully steer individual employment trajectories post-release.