Many convicted individuals do not enter or complete treatment programs in prisons, which limits effective rehabilitation and prevention of recidivism. Treatment readiness is suggested to be an important construct when addressing this problem. Nevertheless, the underlying processes (e.g., how readiness factors interact) are not well studied, and even less is known regarding readiness in the sub-population of individuals convicted of sexual offenses. This paper aims to open up the “black box” and explore psychosocial and context-specific processes behind treatment readiness from the vantage point of the individuals’ lived experiences. In-depth interviews were conducted with 19 adult men convicted of sexual offenses in Swedish prisons, treatment participants (N = 13) as well as non-participants (N = 6). The thematic analysis illustrates readiness obstacles in terms of unintended antagonistic forces in the correctional system operating in the opposite direction of rehabilitative objectives. Nonetheless, a hypothesized relational mechanism, looping disruption, initiated by a non-punitive and supportive response (from prison staff, therapists, close ones, or inmates) to the convicted individual’s negative behaviors or emotions, appeared to reverse such negative, punitive loops, contributing to the mobilization of treatment readiness. Implications for theory, policy, and practice are discussed.