With the first commercially available smart insulin pens, the predominant insulin delivery device for millions of people living with diabetes is now coming into the digital age. Smart insulin pens (SIPs) have the potential to reshape a connected diabetes care ecosystem for patients, providers, and health systems. Existing SIPs are enhanced with real-time wireless connectivity, digital dose capture, and integration with personalized dosing decision support. Automatic dose capture can promote effective retrospective review of insulin dose data, particularly when paired with glucose data. Patients, providers, and diabetes care teams will be able to make increasingly data-driven decisions and recommendations, in real time, during scheduled visits, and in a more continuous, asynchronous care model. As SIPs continue to progress along the path of digital transformation, we can expect additional benefits: iteratively improving software, machine learning, and advanced decision support. Both these technological advances, and future care delivery models with asynchronous interactions, will depend on easy, open, and continuous data exchange between the growing number of diabetes devices. SIPs have a key role in modernizing diabetes care for a large population of people living with diabetes.