Prospective retirees must decide when to stop working and when to claim Social Security retirement benefits. Information about how work and claiming are connected is conveyed in a mailing to prospective retirees, and by online resources detailing the tradeoffs. Still, many prospective retirees do not fully understand the implications of these joint decisions, given the complex formulas and uncertainties. This project assesses how well prospective retirees understand the impact of continuing to work on Social Security benefits, as well as their confidence in understanding this issue. It also explores the effects on people’s understanding of the tradeoffs of two alternative presentations: one that graphically describes the actuarial properties of the trade-off, and one that aggregates earned income and Social Security benefit streams, rather than showing SSA benefits in isolation.