Both international instruments and supranational jurisprudence impose a positive obligation upon national authorities to asist prisoners to maintain contact with outside world. Rights to be visited, sending and recieving letters, making telephone calls or leaving prison due to particular purposes under special permission all play a crucial role in the process of an offender’s treatment and reintegration into society as well. However, importance of compassionate leave enabling prisoners to pay a special visit to relatives suffering from a life-threatening disease or to attend funerals if loved-ones passed away can in no way be compared with others, as that type of permissions mostly rest upon humanitarian grounds. Law no.5275 on Execution of Criminal Sentences and Security Measures had only given convicts such a chance with considerable restrictions till a number of amendments made in relevant provisions between 2011 and 2013. Amendments that improved the legal framework not only eased the process, but also included detainees in the scope. In this article, compassionate leave granted to detainees and convicts on the occasion of their relatives’ death or life-threatening illness is discussed on the base of legal amendments and its implemantation.