Diabetes-related complications, including hypoglycemia, hyperglycemia, and diabetic neuropathy with foot ulcers, present significant health challenges in Canada and the USA. Advances in wearable technology have helped with early detection and ongoing monitoring, improved patient outcomes, and reduced healthcare costs. This chapter provides a narrative review outlining the role of wearable health devices, such as smartwatches, continuous glucose monitors (CGMs), and other digital health tools in diabetes management, emphasizing their applications, effectiveness, and challenges, based on a review of articles from 2018 through 2024 focusing on secondary data from peer-reviewed articles, government reports, and case studies. Additionally, it examines regulatory policies, accessibility barriers, and health equity concerns in these regions. The review highlights the potential of wearable technologies to support in-place care and empower self-management while addressing the need for improved affordability, expanded access, and targeted education programs for underserved communities to enhance the effectiveness and adoption of these innovations in diabetes care. This research seeks to contribute to a better understanding of the role of wearable technology in improving health outcomes in Canada.