Chapter 2 examines Israel’s foreign policy amid the rise to power, in 1992, of the Labour party under the leadership of Yitzhak Rabin. It explains how Israel redirected its foreign policy from entrenchment to engagement, which rested on three pillars: scaling down the Israeli occupation, relinquishing territory in exchange for peace agreements with the Arab states, and putting a premium on diplomacy in Israel’s Middle Eastern foreign policy while keeping military force as a viable foreign policy tool. The chapter accounts for the decision-making process during key events such as the deportation of 415 Hamas members, Rabin’s failed peace proposal to Syria, via the ‘deposit’, and the decision to launch the Oslo peace process with the Palestinian Liberation Organization (PLO). The chapter adds to the literature in two ways. First, by providing new information on Israeli foreign policy decision-making towards the peace processes with Syria and the PLO. Second, by tracing how and why Prime Minister Rabin and Foreign Minister Peres imposed engagement, as Israel’s preferred post-Cold War foreign policy stance, on the government and the security network.