This randomized trial evaluates whether automated telephony could be used to perform daily assessments in 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, 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. The outcome variables were analyzed using linear mixed models. The intervention group showed greater improvement than the control group in the summary scores (M = 9.6, 95% confidence interval [CI] = [0.5, 18.7], p = .038), in mental symptoms (M = 4.6, CI = [0.2, 9.0], p = .042), in alcohol drinking (M = 0.8, CI = [0.1, 1.4], p = .031), in drug use (M = 1.0, CI = [0.5, 1.6], p = .000), and in most stressful daily event (M = 1.9, CI = [1.1, 2.7], p = .000). In conclusion, automated telephony may be used to follow up and to give interventions, resulting in reduced stress and drug use, in paroled offenders.