Organizations for decades have offered a myriad of health benefit options designed to engage employees in their own personal health. These programs have been aimed at supporting a healthier workforce in hopes that, a healthy workforce would also equate to a more productive and engaged workforce. As a result, organizations have developed a myriad of choices that employees can choose from to enhance their personal health (i.e., wellness programs, assistance counseling, health risk assessments, etc.). From a workplace perspective, research in the Human Resource Development (HRD) field, as well as related disciplines, have started to explore connections between work and health. Despite emerging research on work and the working experience, organizationally focused health and wellness offerings have been historically absent from most models of work in HRD. The purpose of this research was to examine how work and the working experience influenced employee decision points around personal levels of health engagement. Using two multiple regression models with data from 206 participants working at a Fortune 500 global logistics company, we explored the linkage between work, health, and employee agency in participating in corporate wellness programs. Through our work, we contribute to traditional engagement theory as well as an emerging framework in HRD— Work Determinants of Health (WDOH)—and provide practical suggestions for how leaders could prioritize employee wellness and health engagement within their organization.