The legal academy has made surprisingly little systematic effort to understand the barriers to corporate engagement in pro bono assistance and the strategies most likely to address them. This article seeks to help fill the gap. It explores the development of pro bono among in-house attorneys, analyzes the barriers to corporate pro bono engagement, and identifies some of the best practices that corporations employ to increase pro bono participation within their legal teams. It draws both on trade and academic publications, and on original empirical research involving some two hundred responses to a survey distributed through the Association of Corporate Counsel (ACC) and the Corporate Legal Operations Consortium (CLOC). Those responses, amplified by selected follow-up interviews and published sources, offer a window into the challenges and opportunities for corporate pro bono programs.