Medication adherence is defined as the extent to which a patient takes his or her medication as prescribed by their healthcare provider. One third to one half of all patients in the United States do not take their medication as directed, resulting in nearly $100B in avoidable hospital costs per year. Recent efforts to improve medication adherence in patients with multiple comorbidities have turned to case management and disease management programs. Connected monitoring devices offer an alternative- or supplement- to frequent nurse visits and outreach. These devices enable frequent monitoring and intervention but can also generate large volumes of data that can be difficult for care teams to manage. The present study explores the use of one such device- a technology-enabled, connected pillbox. Given the continued emphasis on bending the cost curve in US healthcare, clinical validation of tools that may improve the management of costly chronic diseases, such as diabetes, is essential.