This article investigates the challenges facing decentralised governance in poor and underdeveloped areas in Eastern Indonesia. The Timor Tengah Selatan (TTS) regency in West Timor in Nusa Tenggara Timur province is taken as a case study. Indonesia’s radical decentralisation programme applied a national model of decentralised governance, not taking into account the different conditions applying to disadvantaged regions (daerah tertinggal, DRs). In the TTS regency, decentralised governance is underperforming in two core areas – administration and fiscal viability – while making some progress in political decentralisation. Governance is restricted by limited social capacity, a poor resource base, and a lack of investment capital and infrastructure. The question then arises: if the uniform model of decentralisation is not performing adequately in TTS, is there a more appropriate model of local governance and central subnational relations that can better perform in DRs? While not detailing the features of a new model, this article identifies the areas requiring policy development.