On July 28, 2013, Israel agreed to release 104 Palestinian prisoners, clearing a final hurdle to re-starting Israeli and Palestinian negotiations after a three-year hiatus. This gesture, seen as long overdue by the Palestinians, was seen as giving into terrorists by the Israelis. Given the fact that many in the Israeli governing coalition openly oppose a two-state solution, and Palestinian frustration with the U.S.-led negotiation process led to its bids for statehood at the United Nations in 2011 and 2012, what explains the parties’ return to the negotiating table? Twenty years after the signing of the Oslo Accords, Israeli settlements have dramatically expanded, Palestinians are internally fragmented, and little to no progress has been made on the core issues under contention. Given these inopportune aspects, along with a general opinion among many policy makers and scholars that the Oslo peace is highly problematic, if not defunct, why are the parties coming to the table now? In order to answer this question, we will explore contending negotiation and decision-making models, including the concept of “ripeness”, utility maximization versus risk aversion, the framing of risky choices, and the contingency model for third party interventions. After applying different explanatory models to the case of the Israeli-Palestinian negotiations, we will discuss their strengths and weaknesses and ascertain which model best fits the current reality.