Mobile tablet devices and applications have the potential to help type 2 diabetes patients in the self-management of their disease. However, users must be equipped with an appropriate level of digital literacy in order to use the tools and technologies effectively. This study reports from an exploratory mobile health (mHealth) pilot program that was conducted at a large, local clinic in Canberra, Australia. The research team provided digital training and support opportunities to participants as part of the longitudinal study. The aim of the research project was to examine the diverse range of participant digital literacy and how it impacted on self-management and the adoption of mHealth. Mid-study results from online surveys conducted at 2 and 5 months after enrolling 28 participants in the pilot program revealed that digital engagement is crucial to the patients’ participation in mHealth activities. Support, by way of digital training, was essential to the patients’ sustainable use of the devices and applications for health care.