This is a study of the role that social and cultural context play in Buddhist meditation techniques, especially those that fall under the category of vipassana and related practices. It argues that such contexts inform not only practitioners’ explicit understandings of their practice of these techniques, but also their pretheoretical, tacit, implicit orientations, and even the experiences the practices generate. This is a historically and anthropologically informed philosophical project, but one that also draws upon field-based studies of meditation in particular communities. After discussing some of the basic issues involved in the study of Buddhist contemplative practices, I will discuss several examples of vipassana practices in different cultural, social, and historical contexts, addressing the ways such contexts have shaped the meanings and purposes of the practices. These practices have spanned well over two millennia and have occupied vastly different systems of meaning, from ancient India, where they emerged as techniques of transcending the phenomenal world toward a timeless, ineffable, transpersonal state, to modern North America, where they are taken up by professionals attempting to mitigate stress or to cultivate heightened awareness and compassion. This project traces certain paths that such techniques have taken into the modern world, where they have been reconfigured to take on new meanings and significance, addressing the anxieties, projects, and potentials unique to modernity.