This chapter analyzes the process from the failed Rambouillet agreement to UN Security Council Resolution 1244 (1999) through the lenses of ripeness, readiness, and spoiler theories. It argues that the conflict was “ripened” by international actors who engineered a “mutually hurting stalemate” through NATO’s air campaign and the threat of a ground invasion. The text details how the G-8 agreement, facilitated by a German diplomatic initiative, provided a necessary way out by framing the settlement under UN authority rather than NATO. The analysis highlights the strategic management of Russia by transforming it from a spoiler into a co-custodian that facilitated Milošević’s capitulation. The chapter concludes that the final resolution was a forced settlement imposed by great powers which effectively ended Serbian rule in Kosovo.