This Article explores those features of electronic surveillance that have made it challenging to regulate effectively. In balancing interests, lawmakers must create a workable law for an exceedingly complex topic, rein in law enforcement agents without crippling them, and draw a line between prohibited and permitted conduct despite society's ambivalence about surveillance. This Article demonstrates that lawmakers met those challenges when they regulated traditional wiretapping, but they have failed to meet them in the online context. It argues that the law should extend the significant restrictions on wiretapping to online surveillance, just as judges did in the case of video surveillance in the 1980's. The similarities among online surveillance, video surveillance and traditional electronic surveillance strongly suggest that the legal framework that protects the privacy of telephones and private spaces should be extended to protect the privacy of the Internet.