Historic changes in healthcare reimbursement and payment models due to the Affordable Care Act in the United States have the potential to transform how providers care for chronic diseases such as diabetes. Payment experimentation has provided insights into how changing incentives for primary care providers can yield improvements in the triple aim: improving patient experience, improving the health of populations, and reducing costs of healthcare. Much of this has involved leveraging widespread adoption of the patient-centered medical home (PCMH) with diabetes often the focus. While evidence is mounting that the PCMH can improve diabetes outcomes, some PCMH demonstrations have displayed mixed results. One of the first large-scale PCMH demonstrations developed around diabetes was conducted by the Commonwealth of Pennsylvania. Different payment models were employed across a series of staggered regional rollouts that provided a case study for the influence of innovative payment models. These learning laboratories provide insights into the role of reimbursement models and changes in how practice transformation is implemented. Ultimately, evolving payment systems focused on the total cost of care, such as Accountable Care Organizations, hold promise to transform diabetes care and produce significant cost savings through the prevention of complications.