This paper is the third part of an ongoing research project by Andersson et al. 2014 using Interactive Voice Response, an innovative automatic telephone assessment to study Swedish paroled offenders in the first 30 days after prison. Repeated measures of qualitative reports on daily most stressful events (stressors) and quantitative severity ratings (stress) were used to study the perception of stress in the immediate prison release phase. Adding to the knowledge about prisoners’ reentry by exploring paroled offenders’ perception on daily stressful events and the stress intensity associated with these was the main purpose of this essay. Following a phenomenological approach, daily stressful events could be categorized into social, psychological and physical stressors and an insight in the everyday complexities through the reports of paroled offenders could be provided. While social stressors build the largest category, physical stressors are on average perceived as most severe. Overall stress severity shows an increase over the duration of the study period. The findings further support the feasibility of daily automated telephone assessments in the context of the Swedish Prison and Probation Service. Keywords: immediate prison release, Interactive Voice Response, paroled offenders, stress & stressors, transition phase