This paper examines the opportunities,challenges and constraints of undertaking community-baseddevelopment (CBD) programming in Timor-Leste, particularlythrough the lens of community-based provision ofeconomically productive infrastructure. During an extendedperiod of weak central governance in the aftermath of TimorLeste s turbulent independence struggle, external actorsmainly foreign donor agencies and international NGOs broadlyfavoring a community-based approach played a dominant rolein the country s reconstruction. In light of Timor Leste spolitical history and geographic isolation, it is notsurprising that weak social capital and logistical obstacleshave hampered CBD efforts, leaving Timor Leste with a mixedtrack record of success. Based on a longitudinal stocktaking of CBD projects and face-to-face interviews with keyactors in government, NGOs and the donor community, threespecific initiatives are examined in detail with a view toelucidating key successes, constraints and opportunities aswell as lessons learned that can inform the shifting policy environment.