On March 15, 2007, a landmark was reached when the word wiki entered the Oxford English Dictionary Online, after the technology had existed for just under 12 years. Wikipedia's heritage stretches much further back, though, to the many early encyclopedia and knowledge-gathering projects of the ancient world and the impetus to understand the world during the Enlightenment era. In more recent times, the technological developments of the personal computer and the Internet made both wikis and Wikipedia possible, and the free software movement provided Wikipedia with its philosophical stance. This rich history has helped define Wikipedia's goals to provide free information to everyone in the world in their own language and to do so in a transparent, collaborative, dynamic, and open manner. Free software has also given Wikipedia its content license: the GFDL, which ensures that content will remain open, accessible, and freely reusable by anyone. These goals have been a part of Wikipedia since the site's beginnings in 2001. For all its idealism, however, the site has certainly not been immune to criticism of both the model itself and the implementation; in this chapter, we presented some case studies illustrating these criticisms.