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Teens have emerged as a significant market segment, especially with respect to online goods and services. This increased market presence is likely to foreground the contract infancy doctrine, which permits a person under age eighteen to void a contract with a few exceptions. This article provides solid foundations for a discussion of where the doctrine fits in the face of a rising youth market and the digital revolution. Part II covers the general parameters of the infancy doctrine and dispels the notion that the doctrine will not be applicable to online services. This part critiques the one case that has addressed the infancy doctrine in the online arena — A.V. v. iParadigms, LLC. Although this case appears to create or expand an infancy doctrine defense based on the use of benefits, the court misapplies the law. Part II also addresses a possible secondary explanation of iParadigms and the seemingly eternal question of whether the infancy doctrine can be used as a “sword,” whatever that means in various jurisdictions and contexts. It then explores a variety of infancy doctrine defenses and illustrates that they are sufficiently narrow to provide little comfort for online vendors and service providers. Part III focuses on the peculiarities of online contracting. It briefly provides context for the current state of contract law doctrine and the increasing laxity in maintaining traditional protections. This part then reviews the major objections to enforcing many terms of service or end-user agreements and assesses whether other contract doctrines provide sufficient basis for policing their abuses. Part III then concludes that, if the infancy doctrine needs to be limited to better accommodate current market needs, the online licensing agreement is not the best place to begin. Part IV predicts the collision of the infancy doctrine and a market ever more greedy to engage minors. It addresses minors’ economic power, whether online businesses are less at risk because they do not take cash, and the extent to which a parent or other entity secondarily guarantees the payment of online financial promises. It next considers the more subtle economic costs associated with minors’ ability to avoid contract terms even if the service is free or the right to payment is not challenged. Lastly, Part IV outlines the options available and offers recommendations for how online service providers could and should respond to an upswing in infancy doctrine claims. Certainly, the infancy doctrine may become an unmanageable factor in digital market economics. But dramatic changes in contract law should not occur without serious consideration of historical values and long-term implications, especially in an arena where the risk of contract abuses is increased. At least with respect to online agreements, the infancy doctrine should be enforced — and perhaps publicized to encourage its use.