The biomedical definition of comorbidity belies the complexity of its lived experience. This article draws on case studies of women with diabetes and various comorbidities in New Delhi, India, to explore intergenerational transactions surrounding suffering in contexts of comorbidity. The analysis synthesizes sociological theories of chronic disease work, psychological theories of caregiver burnout, and anthropological approaches to suffering and legitimacy to explore how, when, and by whom women’s comorbid sources of suffering become routinized in everyday life. The analysis demonstrates, first, that comorbid suffering is not simply a matter of the addition of a second source of suffering to an existing one; rather, it comprises complex interactions between suffering, disability, family dynamics, and quality of life. Second, it illustrates several social routes through which comorbid suffering can fade into the background of everyday life, even when it is severe. Close attention to how suffering works in cases of comorbidity will be important as comorbid conditions become increasingly commonplace around the world.