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Pharmacies are key sources of medication information for patients, yet few pharmacies have implemented appropriate practices to serve patients who have low health literacy. To better understand facilitators and barriers to pharmacies' adoption and implementation of health literacy tools, we conducted a comparative case study of eight heterogeneous pharmacies, guided by Rogers's Diffusion of Innovations model. Data was collected through interviews, site visits, and review of documents and analyzed using cross-case analysis. Several factors related to the characteristics of the pharmacy and the tools affected decisions to use the tools or not. Facilitators to implementation included staff resources, leadership support, technical assistance (e.g., guidance on how to do focus groups, access to an electronic version of the pharmacy staff survey), and the ability to implement discrete sections of the tool. Barriers to implementation included the overwhelming length of tools, lack of leadership support, and pharmacies' unpredictable, fluctuating workload. The results from the case studies provided several key lessons learned and insights that helped shape the final phase of the project. Specifically, during our recruitment efforts we found that individuals connected to a college or school of pharmacy expressed the greatest interest in using the health literacy tools. Moreover, during our case studies the majority of pharmacies actually willing and able to implement one or more of the health literacy tools—and especially the Assessment Tool—had a pharmacy practice faculty, resident, or student spear-heading the efforts. These findings led the project team and ´óÏóÊÓƵto explore the value of further supporting faculty, residents, and students in future health literacy/quality improvement initiatives by providing curricular modules to ultimately improve the health literacy practices of pharmacists and pharmacies.