JRR Tolkien and CS Lewis are famous for their critiques of technology in its form as industrialized and urbanized society. Both of them cast villains as proponents of technology. Tolkien describes Saruman, through the mouth of Treebeard, as having a mind of gears and metal. Lewis’ s Filostrato from That Hideous Strength describes his ideal world as containing metal trees that he can move and re-configure at will. These critiques are reinforced in their letters and collected writings. Tolkien and Lewis were critiquing technology in one aspect, but it is not clear that the same critiques apply to the modern world. Our technology now has shifted from being industrialization to virtualization. Put another way, technology is now data-oriented rather than machine oriented. I propose that some of the same critiques do apply to virtual technology. It still mars the landscape, though it may not be quite so obvious. This paper will engage the philosophy of digital/information technology as well as Tolkien, Lewis, and their derivative writings as the basis for this discussion.