Abstract: This paper addresses the evolution of metaphors for the Internet and shows how they have constrained and determined the development of cyberlaw. Within the law, metaphors mold the framework of discourse, determining the scope of appropriate questions about and answers to various social and legal problems. Courts and commentators employ metaphors as heuristics to generate hypotheses about the application of law to novel, unexplored domains. Metaphors structure the way lawyers conceptualize legal events, as they infiltrate, consciously and unconsciously, legal discourse. Under the classic formalist view of common law analogy as syllogism, analogical reasoning from precedent begins with the establishment of a rule behind a case or group of similar cases. Judges then apply the rule fairly mechanically to the case at hand to yield a result that is understood through the background of precedent. In contrast to figurative literary metaphors, highly structured analogical, metaphorical mappings may be used to make persuasive, logical arguments. Like all metaphors, however, legal metaphors possess a paradoxical quality, embodied in the constant tension between the legal metaphor's literal incongruence and metaphorical congruence with reality. Metaphors whose metaphorical congruence with reality is perceived as dominant, such as the "marketplace of ideas" metaphor in First Amendment jurisprudence and the "bundle of sticks" metaphor in Takings clause jurisprudence, will continue to have analogical value and will be perpetuated through judicial opinion and scholarly commentary. Conversely, legal metaphors erceived as having greater literal incongruence with reality, such as the slavery metaphor of African Americans as chattels, will lose their value and be discarded. While metaphors aid humans in comprehending abstract concepts and legal doctrines, they also may limit human understanding by selectively highlighting various aspects of an issue while suppressing and marginalizing others. Unreflective use of metaphors can lead lawyers to take for granted the "realities" that metaphors enable. A bad metaphor can also simply lead to bad decision making. For example, Cass Sunstein argues that the "marketplace of ideas" metaphor has turned the right to free expression into a degraded form of commerce. This paper seeks to explore the evolution of metaphorical inferences as applied to the Internet within legal commentary and judicial opinions. Three metaphors in particular will be examined: the information superhighway, cyberspace, and the Internet as "real" space. Given the Internet's ongoing evolution as an unstable and ever-changing technology, courts and commentators have faced perpetual difficulty in mapping metaphors to it. Changing social constructions of the Internet as necessitated by its evolving underlying technological architecture have supported, or conversely eroded, a particular metaphor's literal congruence with reality. The purpose of this paper to make transparent the different conceptions of the Internet courts and commentators are sub silentio employing, and the various sociological, technological, and ideological conceptions of the world that support them.