One of the most consistent findings in literature on the termination of criminal careers concerns the successful resolution of obstacles to reform by a would-be desister. In order to better understand the role of probation supervision in encouraging the processes associated with desistance, the Tracking Progress on Probation project investigated the effects of probation supervision on the criminal careers and behavior of 199 probationers. This chapter provides an outline of the main findings, highlights the complex and interdependent relationships between the main variables of interest, social context, motivation, and probation supervision, and examines the implications of the findings for probation work. Finding highlights include: (1) probation supervision appears to have had little impact upon the resolution of obstacles by probationers and (2) motivation and social and personal circumstances appeared to have been far more important factors in determining the extent to which obstacles were faced and resolved, producing desisters. In conclusion, it appears that probation is slightly missing its target. References