Debates typically invoke an image of individuals arguing over the merits of opposing viewpoints. However, the term has a softer, more deliberative sense that connotes reflection, discussion, and consideration. The 2009 WebWise conference, titled "Digital Debates," was conducted in this spirit, with panelists and attendees engaged in complex discussions about emerging digital media and their role in cultural and educational institutions. The discussions focused on key questions facing museums, libraries, and related organizations: How do institutions strike a balance between their own missions and the needs of communities when developing social media strategies? What are the rights and responsibilities of cultural institutions to their collecting missions and to their audiences? How can institutions collaborate to leverage resources and outreach without compromising organizational identity or brand? And in these uncertain economic times, what strategies are needed to balance innovation with the demands of maintaining core services? Experts addressed these issues in four major sessions whose formats varied from discussions to provocations to formal presentations. Serving as "bookends" to these sessions were two keynote addresses that explored the effect of cloud computing and the next generation of Internet users on cultural institutions. Woven throughout the formal program were impromptu debates posed during question and answer (Q&A) periods and in a back-channel forum ("Today'sMeet") where attendees contributed to a live, online comment stream. This report provides another, more traditional, format--that of a "conference proceeding." It includes speaker biographies, information on project demonstrations, and full text of the keynote papers. It also includes a summary of all the WebWise sessions and the discussions they engendered about important digital debates within the cultural community. The sessions' topical pairings (e.g., online communities and institutions, rights and responsibilities, identity and collaboration, edge and core) provided a framework for exploring these debates and uncovering the continuing challenges and opportunities they pose for cultural organizations. (Contains 61 footnotes.) [The Pre-Conference Workshop section of this report was written by IMLS Senior Program Officer Charles Thomas.]