This paper describes some of the major points of progress and challenges in health management of dairy cattle in the last 25 yr. A selection of the leading contributors in the field is acknowledged. Specific advances in the areas of transition cow management, epidemiology, udder health, applied immunology, housing design, calf health, and health-monitoring tools are described. The greatest advances in dairy health in the last 25 yr have been the shifts to disease prevention, rather than treatment, as well as from focus on individual animals to groups and herds. A fundamental advancement has been recognition of the multifactorial nature of almost all diseases of importance in dairy cattle. Epidemiology has been a critical new tool used to describe and quantify the interconnected risk factors that produce disease. Another major advance has been redefining disease more broadly, to include subclinical conditions (e.g., subclinical mastitis, ketosis, rumen acidosis, and endometritis). This expansion resulted both from improved technology to measure function at the organ level and, just as importantly, from the evolution of the health management paradigm in which any factor that limits animal or herd performance might be considered a component of disease. Links between cattle and people through consideration of environmental or ecosystem health are likely to further expand the concept of disease prevention in the future. Notable successes are decreases in the incidence of milk fever, clinical respiratory disease in adults, contagious mastitis, and clinical parasitism. There has also been improved protection through vaccination against coliform mastitis and bovine virus diarrhea. Since 1980, average herd size and milk production per cow have increased dramatically. Despite these increased demands on cows’ metabolism and humans’ management skills, the incidence of most common and important diseases has remained stable. Great progress has been made in understanding the biology of energy metabolism and immune function in transition dairy cows, the time at which the majority of disease occurs. Coupled with an emerging understanding of how best to provide for dairy cows’ behavioral needs, transition cow management promises to be the foundation for progress in maintenance and enhancement of the health of dairy cows in the next 25 yr.