The Oslo Accords of 1993 promised to bring peace between Israelis and Palestinians, and the Comprehensive Peace Agreement of 2005 promised the same for the Sudanese. These were different agreements designed to deal with different problems in different contexts. But they did reflect a specific approach of liberal peacebuilding that generated almost identical problems. This paper attempts to examine the parallels in the way the two agreements faltered and unravelled, producing what one commentator described as “spirals of insecurity”, becoming the trigger for new rounds of conflict. It argues that the problems do not lie merely in the gradualism and ambiguities of the two agreements, as many have argued regarding the Oslo Accord, but additionally in the continued commitment of the protagonists to mutually exclusive and fervently espoused objectives, thus hampering the cooperation demanded by a gradualist approach. I conclude that in cases where such deep commitments to irreconcilable objectives persist, the gradualist approach should be significantly modified to take account of realities.