This paper looks at the two decades of lessons learned from the development assistance in Afghanistan, with a focus on World Bank experience. It reviews the World Bank–ARTF operations and engagement since 2002 to assess the extent to which they have been relevant and responsive to the country’s temporally evolving developmental needs. The paper studies the effectiveness of the macro-operational features, project designs, and policy approaches of the World Bank–ARTF portfolio in terms of service delivery, organizational-level capacity building, and improvements in governance and institutional environment. Finally, the paper addresses the question of whether the World Bank and the ARTF donors have been able to adapt to reflect the ‘lessons learned’ over time.