This paper examines the Cyprus, Arab-Israeli and Nagorno-Karabakh conflicts as well as their negotiated ceasefires in order to predict the necessary conditions for achieving a mediated ceasefire between Russia and Ukraine. Drawing from these previous cases, this paper argues that a ceasefire agreement would require three primary factors, (1) a state of military fatigue with parties unable to continue fighting (2) significant pressure from external actors who possess influence over the conflicting parties (3) changes in public sentiment or political leadership within Ukraine and Russia.