The objective of this research was to study whether automated telephony could be used in paroled offenders to perform daily assessment of variables associated with recidivismin crime, and whether there are grounds for studying the effects of a brief intervention based on these assessments during 30 days following probation. The design included a randomized controlled trial using automated daily assessments and feedback interventions based on Interactive Voice Response (IVR). Participants included paroled offenders (N = 108) during their first 30 days after leaving prison. All subjects were called daily and answered assessment questions. Based on the content of their daily assessments, the subjects in the intervention group received immediate feedback and a recommendation by IVR, and their probation officers also received a daily report by email. Main outcomemeasures (assessed daily) included Stress (Arnetz and Hasson Stress Questionnaire and a revised version of Daily Assessment of Daily Experience), Mood (SCL-8D measuring depression and anxiety), and Use and Urge to Use Alcohol and Drugs (revised version of the Alcohol Urge Questionnaire). Participants were also asked to rate the severity of their most stressful event that day. The outcome variables were analyzed using linear mixed models, presented as group differences between means, 95%CI. Results indicated that the intervention group showed greater improvement than the control group in stress (9.6, 0.5; 18.7, p = 0.038), depression/anxiety (4.6, 0.2; 9.0, p = 0.042), alcohol use (0.8, 0.1; 1.4, p = 0.031), drug use (1.0, 0.5; 1.6, p = 0.000), and in the severity of themost stressful daily event (1.9, 1.1; 2.7, p = 0.000). There were no differences between the groups in the Stress scale and in craving for alcohol and drugs. Overall, the research suggests that in paroled offenders, automated telephony is an effective technology thatmay be used to follow up and to give interventions, resulting in reduced stress and drug use.