Recent research has demonstrated that poor release planning is associated with sex offender recidivism; however, whether release planning correlates with actual re-entry experiences has not been investigated systematically. Accordingly, in the present study release planning was rated for 16 child sex offenders, and semi-structured interviews about re-entry experiences were conducted at one, three and six months following their release from prison. As expected, significant positive correlations were found between release planning and re-entry experiences across the follow-up period, indicating that higher-quality release planning is associated with more positive re-entry experiences. Accordingly, it can be assumed that re-entry experiences differ between recidivists and non-recidivists, and hence positive re-entry experiences contribute to a reduction in sex offender recidivism. The implications for the management of offender release, policy makers and society as a whole are discussed.