Our encounter with cultural heritage is changing because of the expansion of digital media. Engagement with heritage, particularly for younger people, is often through digital surrogates, such as virtual reconstructions or digital artifacts. Social interactions at sites and heritage discussions are increasingly transferred to the digital sphere. Apart from this independent and uncoordinated digital activity by communities, there is also a growing exploration of its potential by heritage professionals and organizations. Besides using information technology initially for data capture and the management of collections and sites, numerous cultural institutions are also experimenting with digital media to communicate in new ways and attract new audiences. This is a two-way process: not only have digital technologies influenced heritage management and understanding, but wider heritage interpretation issues have also affected how digital tools are being employed. The chapter examines the potential and range of digital heritage applications, and the challenges and theoretical issues these raise.