Workplace wellness programs are extremely popular with employers, aiming to promote better health while preventing and controling diseases for employees and their dependents. Such wellness plans can be incorporated into the employer's group health plan or act as a stand-alone plan. Plans range from providing education about unhealthy lifestyles, to granting financial incentives for attaining certain health standards (e.g., cholesterol level) - the latter with a better chance of improving health and preventing disease. Offering financial incentives under a wellness program is not new. Congress affirmed the use of financial incentives under HIPPA through their expansion under the ACA, in an effort to balance employers' interest in wellness programs against HIPAA's prohibition of discrimination on health status. Recent EEOC regulations are under attack under the ADA and GINA, affirming the use of certain financial incentives in voluntary wellness programs that use medical exams and/or request genetic health information. A district court in the District of Columbia vacated those regulations until 2019, sending the EEOC back to the drawing board in formulating its guidance. In the meantime, employers struggle with offering these wellness programs in the face of potential litigation. This article traces the legal journey that workplace wellness plans have had to travel as they comply with a variety of different federal statutes, each with different goals and outcomes.