This chapter explores the potential for gamesmanship in technology-assisted discovery. Attorneys have long embraced gamesmanship strategies in analog discovery, producing reams of irrelevant documents, delaying depositions, or interpreting requests in a hyper-technical manner. The new question, however, is whether machine learning technologies can transform gaming strategies. By now it is well known that technologies have reinvented the practice of civil litigation and, specifically, the extensive search for relevant documents in complex cases. Many sophisticated litigants use machine learning algorithms – under the umbrella of “Technology Assisted Review” (TAR) – to simplify the identification and production of relevant documents in discovery. Litigants employ TAR in cases ranging from antitrust to environmental law, civil rights, and employment disputes. But as the field becomes increasingly influenced by engineers and technologists, a string of commentators has raised questions about TAR, including lawyers’ professional role, underlying incentive structures, and the dangers of new forms of gamesmanship and abuse.