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Insulin administration remains vital to the treatment of diabetes and although there have been advances in insulin delivery, evidence suggests that many people with diabetes on insulin therapy have suboptimal glycemic management. Recent advancements in insulin administration techniques include connected insulin devices, such as connected insulin pens and pen caps. In this review, we provide an overview of the literature on the use of connected insulin pens and pen caps to further elucidate the clinical benefits and drawbacks of these devices. We discuss the development of these devices, outlining the characteristics of insulin pens and pen caps with regulatory approvals. These devices have different features that can ease the burden of diabetes management, including automatic recording of insulin dose information, tracking of insulin-on-board, bolus calculators, and missed dose alerts. Despite the advantages of connected pens and pen caps, a small percentage of insulin users are currently using these devices, due to many factors, including lack of health-care professional awareness, initial training for prescribers, and setup of the device. Overcoming these barriers and publishing more data demonstrating the glycemic outcomes associated with these systems could improve diabetes management for people living with diabetes. As health-care systems become increasingly digital, connected insulin pens have the potential to allow a data-driven approach to diabetes management for people who are not interested in, cannot afford, or do not have intensive insulin regimens that might warrant use of insulin pumps or automated insulin delivery systems.