For the working rural mother, one key source of support for breastfeeding is the employer. The purpose of this article was to examine workplace barriers and facilitators to breastfeeding in a small rural American community following the passage of the Affordable Care Act in 2010. We used a qualitative research design: semi-structured interviews with major employers and low-income working breastfeeding mothers, and a focus-group with another group of employed and unemployed breastfeeding low-income mothers. While some businesses accommodate breastfeeding mothers, few actively promote breastfeeding. Lack of compliance with the new law, inadequate breastfeeding information for mothers, and lack of support from co-workers and supervisors emerged as the main barriers to successful workplace breastfeeding. To improve workplace breastfeeding support significantly there is need for authentic collaboration among maternal-child and rural health agencies and businesses in creating breastfeeding-tolerant, flexible, and forward-looking work environments that, at a minimum, satisfy the law.