Patients visit their community retail pharmacy on a regular basis to receive their prescription medication and to purchase over-the-counter (OTC) medications for their self-care needs. Despite the availability of written instructions on medication labels and pharmacist education, there is compelling data that patients do not take their medications optimally, and medication errors occur, leading to significant morbidity and mortality. Except for information design of product labeling (which focuses on the patient), the focus of human factors and ergonomics work has been directed on the pharmacist and pharmacy work system, where patients are generally recipients of information and drugs instead of being active and equal team players to the physician and pharmacist. This chapter describes several projects that should be considered as in the early stages of patient ergonomics work in the community retail pharmacy setting. These projects include those that have been conducted to improve the usability and understandability of written instructions on prescription labels and OTC medication packaging. They have further focused on improving patient behaviors for vulnerable populations, such as those with low health literacy and older adults. Moreover, this chapter also presents the impact of physical environment, for example, as illustrated through differences between a pharmacy drive-through visit and an in-person visit. Lastly, a case study illustrates how patient stakeholders and a focus on patient work can inform the development of a system redesign in the community pharmacy to improve OTC medication safety.