The research subject is the conditional release practice of the convicted from district prison. The analysis was performed by considering the risk factors of recidivism that prison and the courts of competent jurisdiction take into account when recommending and granting parole. On the basis of the Ministry of Justice and Public Administration directive (2013), the recidivism risk assessment instrument was introduced in our penal practice, and it was based on the OASys (Offender Assessment System) instrument. In the district prisons practice, The Questionnaire on the Risk Assessment for the Convicts Sentenced to Imprisonment up to Three Years (UPROKZ3) is used for the assessment of recidivism, which is the reduced version of the OASys instrument. The introduction of these instruments should overcome the use of general guidelines when assessing the risk of recidivism and the conditional release proposals, which led to voluntarism and arbitrariness. The research was conducted on a sample of 68 criminal records of the convicts who served their prison sentence in the District Prison in Užice. All convicts were evaluated by the UPROKZ3 questionnaire. During the period between January 2016 and June 2016, the convicts submitted a request for the allocation of parole, and the courts of the competent jurisdiction made decisions to grant it. The research results indicated that the courts of the competent jurisdiction granted parole more frequently than the prison recommended it. Inconsistency between the prison proposals and the courts of competent jurisdiction decisions was observed in 19.2% of the cases.