One fundamental measure of a liberal democracy concerns its guarantee of civil and health liberties to prisoners. The study examines the Israeli legislation regarding prisoners’ human rights and access to health services, and analyzes the reasons for the gap between the regulations and their de facto implementation. The main findings include the following: (a) A significant gap exists between the Israeli Prison Service formal regulations for prisoners’ civil and health rights and their actual implementation, and (b) the Israeli Prison Service and the Israeli legislation lack a pragmatic instrument aimed at the protection and preservation of Israeli inmates’ fundamental human rights.