In the 1990s, artists enthusiastically embraced the creative and archival dynamics of the digital interface. In recounting the parameters of this history and its institutional context, this chapter reflects on the range of interactive interfaces embraced by the artistic community, from the CD-Rom to net.art. While individual artists collaborated with programmers and designers to expand the limits of artistic expression, emergent arts organizations and archives worked with artists to develop portable platforms for their artworks. The expanding power of the internet and informal international networks of new media arts provided unanticipated opportunities for building broad and diverse artistic collectives. In recognition that digital formats were far less stable than initially imagined, preservation developed into a predominant concern of new media art curators, often in tension with the artists’ enthusiasm for the embrace of unpredictable and unstable formats and their affection for the artistic ephemerality associated with performance, installation, and online interaction. Ironically, the archival celebration of memory, interactivity, and digital durability that propelled artistic creation in the early 1990s became the new millennial threat to new media’s archival future.