The use, administration, and monitoring of medications within assisted living residences (ALR) represents an ongoing problem for people who live in, work in, and oversee this type of long-term care. Some proponents argue that these settings should promote the independence, choice, and privacy of residents; but when it comes to medications, these goals create a predicament both within and outside the walls of the ALR. This article defines medication management as a social situation involving multiple actors with complex relations, social worlds, and discourses. Situational analysis is used to analyze data from a 5-year ethnographic study of 6 settings in Maryland. I explain how 2 dominant discourses, safety and autonomy, disguise other important issues by demanding more attention than deserved.