Within a communication predicament of aging and disability framework, this study examined the impact of two types of contextual variation on perceptions of older adult assertiveness within problematic service encounters. Young (N = 66) and older (N = 66) participants evaluated conversational scenarios in which a visually-impaired older woman responded either passively or assertively to denial of requested assistance with reading needed information. Both older and young participants viewed the assertive older woman as more competent and as more likely to achieve her goals in future conversations than the passive older woman. The assertiveness advantage was greater in the community setting than in the hospital and for the more serious situations. Implications for education are discussed. (Contains 2 tables.)