This paper examines civil society organizations’ (CSOs) experiences monitoring Poverty Reduction Strategy Papers and Highly Indebted Poor Country expenditures in several countries, including Bangladesh, Cameroon, Ghana, Uganda, and Zambia. It provides detailed descriptions of CSOs monitoring structures and evaluates the ability of CSOs to monitor effectively. The study concludes that limited access to data, a lack of skilled human resources, and a lack of political will constitute major challenges to the deepening and expanding of CSOs monitoring activities. It also argues that CSOs monitoring is valuable for reasons beyond its effects on fund management, including its contributions to community empowerment and the decentralization of power.