This chapter covers a qualitative analysis of interviews conducted approx. 1.5 years after the release from prison of persons convicted of sex offenses and violent offenders. First, the method is described, covering the interview guidelines, sample recruitment, perspectives of the qualitative interview analyses, and the analyses themselves. The findings offer insights into the post-release realities faced by these offenders, highlighting areas of concern, such as stigmatization, financial challenges, employment struggles, and disrupted social relationships, alongside emotional adjustment difficulties. The qualitative analyses uncover additional themes pertinent to desistance and recidivism, exploring participants’ self-representations, coping strategies, and the interplay of risk and protective factors. Lastly, the chapter delineates different pathways for general and offense-specific recidivists. It concludes with an examination of the concept of masculinity as it emerges from the study’s results, adding depth to the understanding of post-release trajectories.