We examined the complex relationship among work, health, and health insurance, which has been affected by changing demographics and employment conditions in the United States. Stagnation or deterioration in employment conditions and wages for much of the workforce has been accompanied by the erosion of health outcomes and employer-sponsored insurance coverage. In this article we present data and discuss the research that has established these links, and we assess the potential impact of policy responses to the evolving landscape of work and health. The expansion of insurance availability under the Affordable Care Act may have helped reduce the burden on employers to provide health insurance. However, the act’s encouragement of wellness programs has uncertain potential to help contain the rising costs of employer-sponsored health benefits.