This research focuses on diabetic patients who undergo multiple daily injections therapy (MDI) for their diabetic management. MDI therapy is usually considered challenging and difficult to maintain. For this reason, patients might not able to maintain a good level of adherence to the insulin medication. As a step to improve the adherence level among diabetics, we would like to propose a reminder system that can promote a change in the patients’ behavior. This paper is divided into two scopes: the first scope concerns the evaluation of current technologies within diabetic management; while the second scope focuses on testing the proposed system among a number of patients. The results from this usability study demonstrated that there was some improvement within the adherence level among participants. We concluded that these types of systems have the potential to ease the diabetic management and improve the adherence to insulin medication.