The cultural heritage preservation community now functions largely within the environment of digital technologies. This article begins by juxtaposing definitions of the terms "digitization for preservation" and "digital preservation" within a sociotechnical environment for which Google serves as a relevant metaphor. It then reviews two reports published twelve years apart under the auspices of the Council on Library and Information Resources. "Preserving Digital Information" presented an insightful and visionary framework for digital preservation in 1996. "Preservation in the Age of Large-Scale Digitization" explores the implications for preservation practice of the digitization of books and, by implication, our cultural heritage in general. These juxtapositions frame four dilemmas for preservation relating to the impact of environmental storage, new challenges to preservation quality, threats to audiovisual heritage, and an emerging expertise gap. The article concludes with recommendations and observations on making difficult choices.