When the history of healthcare and insurance in the US is examined, it is clear the patient has become more and more removed from the payment process. Insurers including Medicare moved to pay providers more quickly and eliminated pre-payment by the insured customer beyond a typical small co-payment. The patient is not clear regarding costs and lacks incentives to control spending. The payment process has deviated so far from the traditional accounting three-way payment match that fraud and other issues have surfaced in billing and payment error. This article presents suggestions from accounting’s three-way match process used in purchasing to carefully outline problems and challenges in US healthcare. Discussion and ways to adapt the popular accounting framework for healthcare are presented within the historical context of the changing healthcare reimbursement and payment process. Areas for future research are also included.