For many released prisoners, the period following release is characterized by extreme challenges. The ability to overcome such challenges depends on the services, level of supervision, and type of support available. One type of support offered by the Israeli Prisoners’ Rehabilitation Authority provides a supervisory and rehabilitative framework for reintegration after release from imprisonment, with an emphasis on employment. The present study examines the subjective experiences of ex-prisoners on their journey from incarceration through reentry and reintegration while participating in supervision, treatment, and employment intervention operated by the Israeli Prisoners’ Rehabilitation Authority. Semi-structured interviews were conducted with a sample of released prisoners who successfully completed Israeli Prisoners’ Rehabilitation Authority supervision between 2014 and 2019. The interviews reveal four main themes that in turn identify pathways to “better lives” through the reintegration process.