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In recent years elderly men became the fastest growing age group in the prison estate in England. The growth of elderly prison population had significant implications for the prison service. Studies demonstrated high prevalence of chronic mental and physical health conditions among elderly prisoners, many of whom are seriously or terminally ill. English law provides for an early compassionate release of prisoners. However, this provision has been rarely used, because the Secretary of State has unlimited discretion over this issue and no independent scrutiny mechanism exists to check this decisions in terms of reasonableness. While the European Convention on Human Rights does not explicitly protect compassionate early release of prisoners, many situations in which elderly prisoners find themselves might raise the issue of legality of the continued imprisonment. In the light of these developments, the present research examines interplay between compassionate release of elderly prisoners, prohibition of cruel and unusual punishment and right to liberty under the ECHR. It argues that despite the discretionary nature of compassionate release laws and the lack of explicit protection under the ECHR, the continued imprisonment of elderly prisoners in some situations could constitute cruel and unusual treatment or punishment under the ECHR.