Decentralized systems have often been associated with effective and inherent opportunities that promote citizen involvement and improve efficiency in the delivery of local services. This paper presents findings from a study carried out among local government practioners in Uganda that aimed at analysing the evolution of the decentralization system and identifying lessons from its past experiences. Three discussion groups of public officials were organised in the Central, East and Northern Districts of the country and tasked to give account for the decentralisation policy as it evolved in the last twenty-five years. The methodology was qualitative and participants gave their own accounts based on experience as practioners in the system. Findings revealed that the ambitious system that was aimed at giving full transfer of political and administrative powers to local communities had fallen short of its expectations and instead met far-reaching shortcomings and challenges. These included diminished local accountability, insufficient human and financial resources, corruption, patronage, and eventual recall by the central government of some of the transferred functions all of which have restricted the implementation of decentralised reforms and putting participation and efficiency in service delivery at stake. The paper recommends a redefinition of the objectives of the decentralisation policy and embracing the lessons learn in the past implementation process.