In 2008, the Annie E. Casey Foundation (AECF) reviewed its grant portfolios and results achieved to date in order to strengthen its future grant making and operations, including how it funded, planned, and used evaluations. AECF selected Community Science to compile lessons learned by foundation staff from the many evaluations in which they had participated over the years. To accomplish this, we interviewed 19 foundation staff (including the foundation’s evaluation and program staff and senior leadership), the foundation’s evaluation consultants, and evaluation leaders in philanthropy. Community Science’s final report to the foundation included: findings and recommendations to improve the practice and use of evaluation by the foundation; future opportunities, challenges, and trends of evaluation within AECF and in the philanthropy field in general; and the decisions, choices, and lessons learned by the foundation in conducting the evaluation of its the ten-year, multisite comprehensive community initiative, Making Connections. This report informs the foundation and the field about how the practice and use of evaluation has evolved in philanthropy. (2008)