In Western countries, demographic trends indicate an increase in the aging population well into the next century. Because of declining health, many older adults will benefit from residence in assisted living (AL). The purpose of this qualitative study was to explore the experience and contextual influences in everyday decision-making of four older adults in AL using a case study method. Several themes emerged as significant in older adult satisfaction with everyday decision-making (i.e., trigger event, level of physical functioning, inside and outside support systems, past patterns of decision-making). Strategies for assessing and strengthening these contextually relevant factors are discussed.