Bringing community individuals into closed institutions—in some designed to keep their constituencies away from the community—is an effort expected to encounter barriers from the start. Moreover, the art materials coming through the door appear dangerous and the effort to allow an art workshop is not worth it because the non-utilitarian end products seem rather useless. That and the students looking suspiciously like the detainees, to staff unhappy to disturb the status quo, to participants themselves appearing hesitant to start in—make more barriers appear than welcome mats. This chapter explores the reasons to expect such barriers and the solutions to overcome them.