Instant messaging and text chat, online collaborative whiteboards, web conferencing and other synchronous Web 2.0 tools are increasingly finding their way into higher education and are available in both commercially-branded and open source varieties. This chapter describes best practices and challenges in using these new tools, focusing on free and open source software for synchronous course delivery, collaboration, learning activities, and technical support, based on the author’s experience in online teaching and online-teaching support. Synchronous tools can provide immediate and efficient communication for instructors, learners and support staff, fostering community and establishing a heightened sense of social presence. An increasing number of practitioners in the field of distance learning are using synchronous tools to reach their learning and support objectives (Murphy and Rodríguez Manzanares, 2008). Today, free and open-source tools offer similar functionality as costly enterprise systems. This chapter will describe these new open source tools, the types of needs that drive their use, and strategies for effective use and implementation