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This Article analyzes the intersection of three aspects of law, lawyering, and Information Age technology and culture, describing how they disrupt and inhibit one another even as they supply possible opportunities for each to grow and innovate. The Article urges that Information Age challenges to traditional legal institutions and thinking become the foundation for reforms to legal systems and individual lawyering. In embracing changes made possible by emerging technology, the Rule of Law may be strengthened globally and the Preventive/Proactive style of lawyering can be re-invigorated. The Article begins by describing the Preventive/Proactive lawyering ("PPL") style, and offers an example within commercial contracting. The Article analyzes how the adoption of this PPL style has been limited by traditional legal institutions and thinking, described using the metaphor of a container. The effectiveness and cultural acceptability of this containerized legal system is being challenged, however, by Information Age methods and attitudes concerning information and its delivery; the nature of individuals and their social groupings; and the legitimacy and purposes of social control. Emerging Information Age culture, however, is largely compatible with the assumptions underlying PPL. As Information Age technology unfolds, preventive/proactive thinking and methods may not only become more popular in everyday lawyering practice, but also may serve as a model for how traditional legal systems may be helpfully reformed. The Article concludes with a set of design principles by which those reforms may be guided.