Overweight and obesity are directly associated with heart disease, cancer, and diabetes and pose a serious cost-related challenge to employers. As most of the rise in health care spending is traced to the rise in population risk factors, maintaining or reducing the prevalence of disease represents a strategy with large potential payoffs. Tailored communication is a promising communication strategy for influencing health behavior change, including behaviors for weight management. Much of the tailored communication research is based on communication developed for research purposes, yet access to commercially available tailored health programs for worksites is growing. As health risk assessments are increasingly used for setting health programming and insurance priorities in U.S. workplaces and worksites have opportunities to purchase tailored programs, it is important to understand the effect of tailored communication on health risk assessment data. The purpose of this study was to evaluate the long-term effects of a commercially available web-based tailored weight management program on employee weight, body mass index, blood pressure, cholesterol, and blood glucose. The authors compared health risk assessment data at baseline and 2 years later from 101 overweight and obese employees who participated in the tailored weight management program and 137 overweight and obese employees who did not participate in the program. Results show that there were significant mean differences in systolic blood pressure, HDL cholesterol, and blood sugar levels, but each in a clinically undesirable direction. More research is needed to understand the effect of tailored programs used in worksite health promotion.