By most accounts, Blackboard and WebCT are among the most hated pieces of commercial software ever. Yet despite this, the two have captured most of the university learning management software market. When the two companies merged, creating a monolith in educational software, pundits hailed it as an opportunity for open source. What opportunity, though? Despite the hated commercial software, open source alternatives, such as Sakai, Moodle and Bodington still claim only a small market share. We need to recognize that open source software remains, even for those who want to use it, difficult to use and even more difficult to install. We need to recognize that interoperability remains a challenge and that issues such as licensing, patents and digital rights management lurk as hurdles to be faced in the future. And most of all, we need to recognize that open source software, if it seeks merely to emulate commercial software, will always lag behind commercial software. What would a successful open source strategy look like? This talk will look at some successes, and some failures, and draws some conclusions.Keynote, Oct 24, 2005.