How similar or different are so-called neo-trusteeship and traditional United Nations (UN) trusteeship? To find answers to this question this chapter first explores four understandings of neo-trusteeship, ranging from international territorial administration to neo-trusteeship as a governing mode of international politics. Ideas and practices of neo-trusteeship influence international politics to this day, since their unprecedented rise in the early 1990s. However, neo-trusteeship, like its predecessor, has been subject to substantial criticism. By comparing two cases of neo-trusteeship, namely the administrations in Kosovo and East Timor, the chapter discusses two of the most problematic aspects of neo-trusteeship: The still persisting lack of accountability of trustees, and the legacy of dependency fostered by neo-trusteeship in both countries. The chapter argues that, while apparent differences with traditional UN trusteeship exist, neo-trusteeship indeed has failed to substantially “break with the past” of colonial trusteeship, through avoiding control by local populations and its missing support for sovereignty and self-determination. Consequently, neo-trusteeship remains fundamentally contested both conceptually and in practice.