Employment law is currently unequipped to decide rights and obligations in many online work scenarios. We simply do not know how the courts will address the dramatic divergence between existing law and the realities of the modern online workforce. But, it is worth remembering that courts have already grappled extensively with the general question of how to apply existing rules to the Internet. Cases dealing with online property, contract, tort, and crime can help us project how courts might approach the novel and perplexing questions sure to arise in online work disputes.

This Article identifies three basic approaches: (1) the “blind eye,” in which courts essentially ignore the fact that the activity is taking place online and apply existing law without adjustment; (2) analogy or functional equivalency, in which the courts look to directly or functionally analogous real-world legal scenarios to guide their decisions; and (3) “context-driven” analysis in which courts recognize at the outset the crucial differences presented by online environments, then, by disposing of certain doctrinal elements, adding others, or crafting entirely new standards, endeavor to reconcile existing law with situations its authors could never have envisioned.

This Article focuses mostly on cases from the earlier years of cyberlaw, before doctrines developed and legislatures acted. It offers something of a roadmap to practitioners, online employers, and potential employee plaintiffs, explaining how courts and administrative bodies first struggled to cope with the migration of regulable activity into a virtual environment.

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