We presently lack a good theory for when we should permit parties to litigate using a pseudonym, and American and European legal systems differ sharply on the question. This essay attempts to leverage one of the developments associated with the information age to make progress towards a satisfying answer. The relevant development is the newfound ease with which one can air a grievance pseudonymously or anonymously via online feedback sites, rating sites, and similar forums. Given the availability of these sometimes attractive alternatives to litigation, the legal system should answer the question of whether to permit a party to litigate as a “John Doe” by determining whether a particular grievance is optimally resolved via legal dispute resolution mechanisms or the self-help alternatives that have arisen online and elsewhere. These alternative mechanisms are markedly inferior to litigation at addressing certain types of disputes and markedly superior at addressing other sorts of controversies. Many of the factors most relevant to determining whether a dispute is best addressed in a court or in a less costly forum – such as the existence of legal issues of first impression, the public relations sophistication and reputational stakes of the parties, the existence of material factual disputes, the degree to which the parties’ conduct violates existing social norms, and the magnitude of the harms suffered – are not easily discerned at the outset of litigation. It therefore may be optimal to permit a party to litigate to final judgment using a pseudonym and to consider revealing the litigant’s identity at the conclusion of proceedings. Such determinations could be based on either a balancing test that weighs the relevant aforementioned factors or a less precise bright-line rule, such as “prevailing party pseudonymity.” The essay examines how such approaches would have played out in Doe v. Smith, a Seventh Circuit invasion of privacy case that expressed misgivings about permitting pseudonymous litigation despite quite sympathetic facts.