This study has brought together two seemingly socially extreme population subgroups to compare their health and social well-being. These groups had in common restricted living arrangements and aspirational enrollment. As well, they are part of the population-based Thai Cohort Study (TCS) of 87,134 adult Open University students residing throughout the country. Analysis was restricted to men aged 20-39 years resulting in 711 monks, 195 prisoners and 29,713 other cohort members. For physical health, we have found certain conditions such as tuberculosis or malaria much more common among prisoners, while goiter and liver diseases were more common among monks. This could be due to prison living arrangements for the former and region of residence for the latter. For other social outcomes, lower trust, higher economic stress and lower personal well-being was noted for prisoners compared to other groups. Findings here with regard to spirituality and religion are encouraging with almost no difference reported between prisoners and other cohort members implying that trust-building and other social intervention for prisoners could be activated through prevalent religious beliefs and practices and with continuing support from Thai prison authorities.