The reintegration of imprisoned extremist offenders into society is an essential condition for a successful disengagement and deradicalization process. However, several factors can impede reintegration, such as restrictive conditions of imprisonment that complicate transition management. Additionally, strict supervision orders and the police treatment of released offenders as so-called “dangerous persons” can further hinder the rehabilitation and reintegration process. While these factors can negatively impact the sustainability of an ongoing process, this is not always the case. This article examines how released offenders perceive the restrictive conditions of imprisonment and the post-prison control framework, including supervision orders and police monitoring, and how they address the effects on their own rehabilitation and reintegration process. The study focuses on six individual cases of released Islamist extremists who had already begun to distance themselves from extremist ideologies while in prison. Narrative biographical interviews form the empirical basis of the analysis. The article concludes with recommendations for action regarding imprisonment conditions, particularly during transition management, as well as the conditions and instructions imposed by security authorities after release from prison.