Bhutan’s gradual shifting of responsibilities and power from central government authorities to local government bodies was promoted within a history of decentralized practices and as an integral part of transformations in the overall governance system. These phased developments were important preparations for the country’s transition into a Democratic Constitutional Monarchy in 2008, a system that seeks to remain true to both tradition and modernity. Today, local governments in districts and counties are representative institutions legitimized by direct elections. Implementing decentralization has raised nuanced questions that have remained largely at the periphery of mainstream policy discourses. The questions are derived from emerging dynamics, real or perceived, between central and local government institutions, elected leaders and the appointed administration, and new actors and set traditions of decision-making. The decentralization arrangements in the country can be both a cause of and the space to seek solutions to these questions. One may surmise that the purpose of decentralization has been largely development. This is in keeping with broader policy priorities of modernization and development that continues to this day. The ‘twin purposes’ of decentralization, i.e. of development and of empowerment, was part of the original motivations to decentralize to local governments and sees reiteration from time to time. Implementation, however, places intricate demands on the decentralization arrangements as the straightforward tenet of efficient service delivery meets the complexities of power sharing. The chapter seeks to stimulate reflections on these questions within the parameters of the country’s governance history and traditions. In so doing, considering the dearth of research on the effects and implications of the country’s decentralization choices, insights from minutes of Parliamentary discussions, media reports, comparisons between five-year plans, podcasts and various social media platforms have been used to supplement the few publications dwelling into the topic to a serious extent. It concludes by reflecting upon opportunities and context-relevant mechanisms that could potentially mend disconnects, perceived or real, for which decentralization is oftentimes held responsible. A central issue, or possibly solution, lies in finding a balance between centralization and decentralization arrangements suited for the context of Bhutan.