The transition from prison to society is a challenging period for offenders released from prison. Recidivism rates are high, and the offender’s situation can change rapidly. Advances in technology in recent decades have provided new ways for correctional agencies to provide the level of supervision and immediacy needed to help prisoners to successfully re-enter society. One such area of advance is the widespread use of mobile phones and related developments in communication technologies, such as Interactive Voice Response (IVR), an automated telephony system. The overall aim of this thesis is to investigate the feasibility of using IVR to assess and intervene on everyday stress-related acute risk factors for crime among prisoners on parole. Paroled offenders (N=108) performed daily assessment during their first 30 days after leaving prison. Before release, they also completed a baseline assessment of stable risk factors, including personality, substance use problems, and mental health problems. Data on criminal recidivism one year following parole was collected from the Swedish Prison and Parole Service. After release, all subjects were called daily and answered assessment questions. Based on the content of their daily assessments, subjects in the intervention group received immediate feedback and a recommendation by automated telephony, and their probation officers also received a daily report by email. Although the intervention had no effect on criminal recidivism, the intervention group showed greater improvement than the control group on several of the acute dynamic risk factors studied. Several of these factors could predict criminal recidivism with marginal accuracy, and could provide incremental predictive validity beyond the baseline risk level of stable risk factors, i.e. problematic drug use and impulsiveness trait. In conclusion, IVR may be a feasible way to assess and intervene on daily stress-related acute dynamic risk factors among prisoners on parole.