This paper examines the relationship between psychological contract breach and insomnia among older workers (aged 40 years and up). Drawing upon the conservation of resources theory, we conceptualize breach as a stressful event characterized by a perceived threat, failure to gain, or actual loss of valued resources, which increases psychological distress and insomnia. Moreover, we hypothesized that older workers' generativity concerns would act as a personal resource that would buffer the negative impact of breach. We tested our proposed model in 2 studies (Study 1 = 123; Study 2 = 168) of employee–spouse dyads. Results revealed that psychological distress mediated the relationship between psychological contract breach and insomnia. These mediated relationships were significant for those with low, but not for those with high levels of generativity concerns. These effects remained significant even after controlling for perceived organizational support (i.e., a social exchange mechanism). Theoretical and practical implications are discussed.