ABSTRACT This paper explores the ways in which Leonardo da Vinci's anachronistic skepticism of Renaissance perspective and his subsequent invention of sfumato prefigure contemporary digital technology and its ability to literalize this formal technique. Marcos Novak and Char Davies offer parallel theories on the permeable boundaries among objects and between physical and virtual worlds. The resultant theories, like those of Leonardo, offer new conceptions of space and representation that challenge those who suggest the digital world will subvert the physical. Briefly comparing Leonardo's initial revisions to Renaissance perspective to those realized through digital technology, this paper examines radical revisions of the notions of space and boundary and the ways in which those revisions challenge the traditional goal to aptly represent the physical world via linear perspective.