The ever-increasing deluge of unsolicited e-mail, or spam, results in millions of dollars of economic loss, fosters criminal activity, causes un-told user frustration, and threatens to undermine the viability of e-mail as a communication medium. Attempts to stem this tide have thus far been unavailing. The arrival of federal regulation on the scene has not helped matters and, by thwarting earlier state regulation, has created an intractable conflict. On the one hand, narrowly focused state anti-spam laws are now preempted by the federal act. On the other hand, broad attempts to regulate spam, although escaping preemption, collide directly with the First Amendment. This Note examines the marginal regulatory area left in place at the intersection of federal regulation and constitutional boundaries. It further reexamines several assumptions underlying the current case law and regulation of spam, and suggests that altering these assumptions may enable new approaches to deal with this pervasive problem.