This paper is intended to frame and inform a discussion about philanthropy and community change among foundations and others committed to improving low-income communities and the circumstances and opportunities of the people who live in them. Based on interviews with a diverse group of foundations, community change organizations, and evaluators and technical assistance providers, as well as on previous Chapin Hall experience, the paper examines lessons from what has been accomplished to date and reports strategies some foundations have found helpful to address the challenges of this work. The authors identify challenges within three core dimensions of philanthropic activity, how foundations think about community change, how they do their community-change work, and how they learn from their efforts. The paper addresses the clarity, realism and completeness of foundations' goals and strategies, the alignment between foundations' thinking and their practice on-the-ground, and the adequacy of current methods to inform, assess and revise foundation thinking and practice. Interviews suggest that many funders of community change feel that they are at a juncture where critical assessment and debate can lead to increased effectiveness in their community-change work, and they are eager to take on that challenge.