Background: The World Health Organization notes that diabetes, a chronic disease, is a silent epidemic, and by 2020 there will be a 54% rise in the total number of individuals diagnosed with this disease. These are alarming figures that have significant repercussions for the quality of life of individuals and their families as well as for the financial stress of health care systems globally. Early detection and proactive management of diabetes is essential. The Diamond solution provides diabetes self-management by enabling patients to send details about their blood sugar readings at specific times to their nominated care coordinator to receive recommendations for diet and exercise and insulin titration. Objective: The aim of the study was to assess the usability, acceptability, and fidelity of the Diamond diabetes monitoring device for patients with gestational diabetes mellitus (GDM). Specifically assessed were (1) patient compliance, (2) patient satisfaction, (3) level of glycemic control achieved, and (4) health professional satisfaction. Methods: Using a design science research perspective, the Diamond diabetes monitoring device solution was adapted to the Australian health care environment. Once the solution was deemed fit for purpose by the director of the OB/GYN clinical institute and on securing all relevant ethics approvals, a 2-period 2-arm nonblinded crossover clinical trial was conducted for 8 weeks total time with crossover at 4 weeks to establish proof of concept, usability, and fidelity. The patient perspective was assessed by using structured questionnaires at 4 specific stages of the project, while the clinician perspective was captured via semistructured interviews and unstructured questionnaires. Results: The 10 patients studied reported preferring standard care with the technology solution to standard care alone. Further, all clinicians involved concurred that the technology solution greatly assisted their ability to provide higher value patient-centered care. They also noted that it was extremely helpful for assisting in systematically monitoring glucose levels and any/all changes and trends. Conclusions: Based on these initial findings, we offer a holistic pervasive approach to enable the achievement of value-based, patient-centered care in chronic disease management. Key lessons include the importance when designing such solutions to focus on the two primary user groups (patients and clinicians).