This chapter reports findings of a study of five East African Cooperatives (in Kenya and Uganda) that seeks to identify the macro-, meso- and micro-level factors that facilitate and/or block the development of smallholder farmers from gaining greater access to growing milk markets. Methods include in-depth interviews of cooperative boards and management as well as sample surveys of cooperative members. Macro-level economic development factors account for differences between Kenyan and Ugandan cooperatives. Meso-level characteristics of regional milk markets within countries explain additional variance between cooperatives. The most important source of cooperative performance, however, is the quality of cooperative leadership. This highlights the importance of developing cooperative governance experience, technical and accounting skills, leadership training, large organization comprehension, member benefit orientation and principal–agent professional relationship discipline – all attributes necessary for principal-oriented governance and leadership. These issues should be addressed prior to investing resources in development assistance programmes.