One possible explanation for the individual differences in outcomes of stress is the diversity of inputs that produce perceptions of being stressed. The current study examines how combinations of contextual features (e.g., social isolation, neighborhood quality, health problems, age discrimination, financial concerns, and recent life events) of later life contribute to overall feelings of stress. Recursive partitioning techniques (regression trees and random forests) were used to examine unique interrelations between predictors of perceived stress in a sample of 282 community-dwelling adults. Trees provided possible examples of equifinality (i.e., subsets of people with similar levels of perceived stress but different predictors) as well as for the identification both of contextual combinations that separated participants with very high and very low perceived stress. Random forest analyses aggregated across many trees based on permuted versions of the data and predictors; loneliness, financial strain, neighborhood strain, ageism, and to some extent life events emerged as important predictors. Interviews with a subsample of participants provided both thick description of the complex relationships identified in the trees, as well as additional risks not appearing in the survey results. Together, the analyses highlight what may be missed when stress is used as a simple unidimensional construct and can guide differential intervention efforts.