Structured journaling interventions have been used successfully in a variety of settings (e.g., mental health, addiction) and recent research has indicated that journaling with incarcerated individuals may be beneficial in reducing recidivism. The purpose of the current study was to implement and examine the effectiveness of a set of five self-directed workbooks in a community supervision context and evaluate their utility from the clients’ point of view. Despite organizational changes impeding implementation at one site and low participation rates, which led to issues of low power during analyses, the preliminary results combined with previous research suggest that self-directed workbooks may have potential for reducing both technical violations and recidivism among individuals on supervision.