Organizations have become more permeable — integrating more influences from the outside world — as participants engage in such online diversions as trading stocks, engaging in multiplayer games, or viewing images of their children in daycare. Availability of these activities has brought the potential for abuse but also new opportunities. Constructive uses of online recreation and play can enhance many workplaces (especially high-tech and information-saturated ones) and perhaps ultimately make them more productive. Human resource (HR) professionals can become active in exploring and tailoring constructive recreation strategies for specific workplace contexts. Many organizational roles today demand high levels of creativity and mental flexibility, and constructive uses of online recreation can help individuals gain fresh perspectives. This chapter proposes that these complex issues be resolved through participatory approaches, involving workgroups and HR professionals in discussions as to what constitutes “constructive recreation,” as well as in development and dissemination of effective and fair organizational policies.