Retirement-aged workers with chronic conditions are increasingly engaged in late-life careers in the policy context of delayed retirement initiative. However, it remains uncertain as to how chronic conditions and employment-based social health insurance interact to affect health-related working capacity and late career participation in this group of people. Using data from the China Health and Retirement Longitudinal Study (CHARLS) and the discrete choice model, this study finds that chronic conditions are negatively associated with health-related working capacity (- 0.400,  < 0.01) and late-life career participation (- 0.170,  < 0.01). Employment-based health insurance is positively associated with health-related working capacity of retirement-aged workers (0.432,  < 0.01), but is negatively associated with their late-life career participation (- 1.027,  < 0.01). Moreover, employment-based health insurance could weaken the negative associations between chronic conditions and health-related working capacity (interaction = 0.285,  < 0.05) and late-life career participation (interaction = 0.251,  < 0.05). More fine-grained policies for delayed retirement are needed to focus on the long-neglected health of retirement-aged workers with chronic conditions.