The very word monasticism brings to mind images of walls and enclosures, suggests qualities of isolation and separation. As recent work on both medieval and early modern monastic foundations has demonstrated, though, the convent wall was actually quite permeable. In this special issue of JMEMS, essays explore the ways in which monastic foundations are complexly imbricated in their local communities as well as in far-reaching political, economic, and textual systems. One of the aims of this issue is thus to use the topic of monasticism to rethink a variety of boundaries that have long shaped studies of medieval and early modern history, literature, and religion. The essays in this volume consider monastic traditions, institutions, texts, and practices comparatively and internationally. They also consider early modern English monastic communities in their Continental environments.