Journaling has been utilized successfully in a variety of settings (e.g., mental health, addiction) and recent research indicates that journaling with incarcerated offenders may help reduce recidivism (e.g., Proctor, Hoffman, & Allison, 2012). The purpose of the current study was to implement and examine the effectiveness of a set of self-directed workbooks in a community supervision context and evaluate their utility from the clients' perspective. These workbooks were developed to assist probation officers in increasing the community success of offenders. Each workbook targets a different factor (e.g., criminal attitudes, motivation to change) essential to managing offender behaviour. Despite organizational changes impeding implementation and low participation rates (n = 32) which led to issues of power during analyses, the preliminary results combined with previous research suggest that self-directed workbooks may have potential in reducing both technical violations and recidivism among supervised offenders. Implications, limitations, and directions for future research are discussed.