Documentation of prison life is widely recognized as a vital tool to build the collective conscience and to confront the unlawful suppression and denial of Palestinians’ political and legal rights. To date, however, little research has addressed the particular conditions for Palestinian political prisoners from occupied East Jerusalem. In 2008 Addameer published a special paper on the socio-economic and legal challenges facing Jerusalemite prisoners in an effort to fill this gap [1]. The following paper aims to build on this report by discussing the current conditions of Jerusalemite political prisoners in the context of the Oslo “Peace Process” agreements. As well as addressing the interrogation and trial procedures pertaining to political prisoners from East Jerusalem, this paper reviews the history of the Palestinian political prisoner movement during and after the bilateral agreements of the Oslo years (1993-2000), and addresses how these agreements have affected Jerusalemite prisoners’ due process rights and negotiated prison releases. Finally, this paper will highlight the broad socio-legal and political questions surrounding Jerusalemite political prisoners.