The S. D. Bechtel, Jr. Foundation, a spend-down foundation sunsetting in 2020, invested in four major education initiatives during its final decade of grantmaking. A firm believer in the importance of building and sharing knowledge, the Foundation also made significant, complementary investments in evaluation that were intended to help grantee partners improve their work and to capture lessons learned that funders, nonprofits, policymakers, and other education actors might benefit from. This essay offers a high-level comparison of the evaluation approach taken in each initiative and shares reflections on why we took the paths we did.