Devised as a means of downsizing prison population and facilitating the rehabilitation of inmates, employment outside of prison undergoes a limited expansion and a locally differentiated implementation. Actually, the lack of an incentives’ policy, as well as constraining regulations have put the burden of its development on the sole individual and local initiatives, on their capacity to find allies – inside and outside the prison – who accept to participate in its implementation. Furthermore, the measure is perceived as risky by all the actors involved – from the judiciary as from correctional authorities – because it may collide with their common mission of maintaining public safety, a perception that repercuts an additional obstacle to the measure’s implementation.