Digital health management is increasingly pivotal in the care of patients with diabetes. The aim of this review was to evaluate the clinical benefits of using smart insulin pens with connectivity for diabetes management. The search was performed using PubMed and PubMed Central on May 15, 2019, to identify publications investigating the use of insulin pens. Studies evaluating insulin pens with connectivity via Bluetooth/Near Field Communication, with an associated electronic device enabling connectivity, or with a memory function were included in the review. Nine studies were identified in the search. Overall, these studies lacked data on smart insulin pens with a connectivity function, with eight of the available studies investigating only pens with a memory function. The studies focused primarily on assessing patient preference, usability, and technical accuracy. The number of studies assessing clinical outcomes was small (n = 3). However, the majority of studies (n = 8) reported that patients preferred smart insulin pens because they increased confidence with regard to diabetes self-management. These results suggest a lack of published data regarding smart insulin pens with connectivity for the management of diabetes. However, the available published data on usability and patient preference suggest that the use of smart insulin pens holds promise for improving and simplifying diabetes self-management.