Insulin is an effective treatment for achieving tight glycemic control and improving clinical outcomes in patients with diabetes. While insulin therapy is required from the onset of diagnosis in type 1 disease, its role in type 2 diabetes requires consideration as to when to initiate and advance therapy. In this article, we review a case study that unfolds over 5 years and discuss the therapeutic decision points, initiation and advancement of insulin regimens, and analyze new data regarding the advantages and disadvantages of tight management of glucose levels.