In recent years, impacts of information and communication technologies, market enclosures, and the struggle to retain public goods have had significant impacts on the nature of interactions of communities. This chapter examines communities in the context of the knowledge commons–a space by which “a particular type of freedom” (Benkler, 2004) can be practised. It is also an appropriate concept applied to the discussion of communities and the ways they work. As Castells (2003) noted, self-knowledge “is always a construction no matter how much it feels like a discovery,” and this construction is enabled when people work, or associate themselves with each other. In particular, the chapter is concerned about the structure of open content licenses operating within such domains. The chapter first explores the concept of the knowledge commons to understand the types of intellectual property that are distinctive to communities (public, communal, and private). Thereafter, licenses, as a structure, are examined as they may apply within such contexts. A significant influence on the discussion is the contemporary media environment operating in today resulting in the breaking down of boundaries, the blurring of distinctions between an original and a copy, and shifting the nature of production in communities. These debates lead to a case for open content licenses as appropriate structural mechanisms for communities.