The COVID-19 pandemic has led to an intricate disruption of the provision of healthcare worldwide. In Greece, as per March 2021, patient visits to the outpatient medical facilities have ceased due to the widely applied lockdowns and restrictions imposed by the government. Therefore, it has become increasingly hard to sustain the same quality of care to individuals with Diabetes mellitus (DM), a chronic and challenging condition affecting up to 10% of the Greek population.1 Medication-prescribed diabetes, in particular, concerns 720,764 individuals in the country. Emerging evidence regarding the interplay between COVID-19 and anti-diabetic medications has compelled healthcare professionals to reconsider the treatment of these individuals. Although they are at high risk of contracting SARS-CoV-2, at the same time they have limited or no access to healthcare due to the COVID-19 restrictions. This paper reflects on the authors’ relevant experience in the outpatient diabetes center of the hospital “Tzaneio” in the city of Piraeus, Greece during the trying times of the COVID-19 pandemic.