The current study tested the effectiveness of a self-administered, cognitive–behavioral intervention targeting criminal thinking for inmates in segregated housing: Taking a Chance on Change (TCC). Participants included 273 inmates in segregated housing at state correctional institutions. Reductions in criminal thinking, as assessed by the Psychological Inventory of Criminal Styles-Simplified Version, were found in the general criminal thinking score as well as the proactive and reactive composite scores. Examination of demographic predictors of change (i.e., age, years of education, length of sentence) revealed older and more educated participants decreased in criminal thinking more than younger and less educated participants. For a subset of 48 inmates, completion of TCC was associated with significant reduction of disciplinary infractions. Reductions in reactive criminal thinking predicted reductions in disciplinary infractions. Although further research is needed to determine the effectiveness of TCC in reducing recidivism, the reductions in criminal thinking and disordered conduct suggest this is a promising intervention and mode of treatment delivery. By utilizing self-directed study at an accessible reading level, the intervention is uniquely suited to a correctional setting where staff and monetary resources are limited and security and operational issues limit the feasibility of traditional cognitive–behavioral group treatment.