This study analyzes the firm’s decision to offer and contribute to retiree health insurance. We apply a binomial probit model and an interval regression model to analyze the likelihood of offering and the proportion of costs contributed by the firm. Our findings indicate that while firm characteristics affect the probability that a firm offers retiree health insurance, financial performance and alternative insurance options significantly affect the firm’s generosity towards its cost. This study expands on previous research by including potentially important policy-related measures to the more limited set of firm and workforce characteristics that have been typically employed.