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The United States detains more people per capita than any other country. This may be related to criminal justice policies that focus more heavily on punishment than on helping people successfully reintegrate after incarceration. This exploratory study aimed to compare a country that has improved its recidivism rates, post incarceration, to the United States, and to examine possible explanations. Singapore, despite strict criminal laws, invests in programs that support people while they are incarcerated. In addition, Singapore has invested in reentry reform and policy to help people reenter society after incarceration. Using survey methodology, we examined self-reported psychological needs of autonomy, competence, and relatedness in a male population reentering society after incarceration, comparing the U.S. (n=34) and Singapore (n=17). Results demonstrate statistically significant differences with participants in the U.S. reporting higher levels of autonomy, competence and, unexpectedly, relatedness. Our findings reflect how cultural values shape people’s experiences when reentering society after incarceration. Future research will expand the study to more participants in the U.S. and Singapore.