This chapter analyzes the failure of the Vienna Talks (2005–2007) regarding Kosovo’s final status through the lenses of ripeness, readiness, and spoiler theories. It argues that the conflict was “unripe” for resolution due to the absence of a “mutually hurting stalemate” for Serbia, which relied on a diplomatic “shield” from Russia to resist compromise. The text highlights an asymmetry in readiness, where Kosovo accepted the Ahtisaari Plan’s supervised independence while Serbia, acting as a “total spoiler”, rejected any loss of sovereignty. Consequently, the deadlock in the UN Security Council and the failure of the subsequent Troika process legitimized the Western “departing train” strategy, which paved the way for Kosovo’s coordinated declaration of independence.