This chapter addresses the collaborative aspects of digital libraries as a special case of Computer Supported Collaborative Work (CSCW). Libraries always had social and cultural roles, and worked as a dedicated place for learning, research and sometimes also for opinion exchange and debates. The Internet era gave birth to digital libraries which can also represent a whole range of collaborative functions. The suitable collaborative functions are different for young students, general public or scientists and also different in the view of the user’s goals, such as finding content, finding answers or creating new content. The collaborative aspects of these library functions are described here in details with typical examples. Despite of these examples, many librarians think that digital libraries failed to ride the waves of emerging web technologies, and current digital libraries cannot serve general information needs well enough, so they are not among the first sources of information and collaboration support any more. An important moment in the evolution of DL systems was the appearance of Web 2.0 technology and social computing. The Web 2.0 brought not only fancier user interfaces, but enriched functionality for building communities and collaborating extensively through the Web. Library 2.0 was the late response of the librarian community for social sites, since Library 2.0 is user-centered, with focus on rich social interactions through multi-media content. Moreover, for many, Library 2.0 is not about technology, but about a new philosophy of constant evaluation and innovation with the help of library users. In fact, Library 2.0 allows the users to change the library in many ways. The challenges for libraries within the Web 2.0 era are summarized here, along with the research issues waiting to be solved, as we think that the prospects of collaborative functionalities are far reaching and they could become a key motivation for using digital libraries.