Background: Insulin treatment is an essential hormone replacement therapy for the survival of people with type 1 diabetes and is often used for treatment in type 2 diabetes, particularly as the disease progresses. Advances in insulin therapy have been made since its discovery, including production of human insulin and development of insulin analogs with improved efficacy and safety profiles. The different types of available insulin formulations allow health care professionals to personalize treatment to an individual’s needs. Generally, insulin requires parenteral administration via subcutaneous injection owing to very low oral bioavailability. Methods: This article reviews the human, technological, economical, and regulatory factors affecting the performance of insulin pens and the relationship between them. Opportunities and challenges that insulin pen injections may encounter in the future are also considered. Results: Insulin delivery devices, together with other factors, influence dose accuracy, convenience, and quality of life, contributing to easier medication administration with high efficacy and safety. For patients, ease of use, fast and accurate drug delivery, and painless injection are the most valuable features of an insulin injection device. For manufacturers, technological feasibility and economic viability also need to be considered when developing injection devices. Conclusion: Insulin pen injectors are generally preferred over vial and syringe, although access may be limited in some health care systems. Insulin pen injectors can adapt to different insulin regimens and formulations and have the potential to acquire dosing data in real time.