BACKGROUND: The Deep South of the United States, and Louisiana in particular, bears a greater burden of obesity, diabetes, and heart disease compared with other regions in the United States. Throughout the COVID-19 pandemic, there has been a substantial increase in telehealth visits for diabetes management to protect the safety of patients. Although there have been significant advancements in telehealth and chronic disease management, little is known about patient and provider perspectives on the challenges and benefits of telehealth visits among people living with diabetes and providers who care for patients with diabetes in Louisiana. OBJECTIVE: This study aimed to explore barriers, facilitators, challenges, and benefits to telehealth for patients with diabetes and health care providers as they transitioned from in-person to remote care during the early COVID-19 pandemic to understand potential optimization. METHODS: A total of 24 semistructured qualitative interviews were conducted with 18 patients living with diabetes and 6 clinicians who served patients with diabetes to explore their experiences and perceptions of telehealth services for diabetes care. Approximately half of the participants identified as Black or African American, half as White, and 75% as female. Interviews were recorded, transcribed, and coded by experienced qualitative researchers using inductive and deductive techniques. A narrative, descriptive approach to the patient and clinician journey framed the study, including the development of internal journey maps, and reflexive thematic analysis was applied to the transcripts, with special attention to barriers and facilitators. RESULTS: In total, 5 themes illustrated barriers and facilitators for participants: convenience, safety, and comfort are the benefits of telehealth for patients and clinicians; yet telehealth and in-person visits are valued differently; the convenience of telehealth may have a downside; technology acts as a double-edged sword; and managing expectations and efficiency of the visit experience was an important factor. Individual experiences varied in relation to several factors, including comfort level and access to technology, health system protocols for providing telemedicine, and level of diabetes control among patients. CONCLUSIONS: Recommendations for optimization include providing support to help guide and inform patients about what to expect and how to prepare for telehealth visits as well as allowing clinicians to schedule telehealth and in-person visits during discrete blocks of time to improve efficiency. Further research should address how hybrid models of telehealth and in-person care may differentially impact health outcomes for patients with diabetes, particularly for people with multiple chronic conditions in settings where access to technology and connectivity is not optimal.