Today, in many western countries, acceptance of alternate forms of healthcare such as Chinese medicine (CM) is increasing. In fact, countries such as Australia, Canada, and England are going so far as to set regulations, education, and standards regarding the practice of CM in these respective countries. Further, we can see the integration between western and Chinese medicine delivery of care and treatments in many instances. Information Systems and Information Technology (IS/IT) can be a key enabler in assisting this integration. The following study examines aspects of such integrations using IS/IT and identifies that CM IS/IT is more likely to succeed when there is synthesis between key aspects of the unique environment and user requirements. This perspective is supported theoretically by adapting Churchman’s Inquiring Systems to frame CM as a combination of Hegelian and Kantian inquiring systems with the support of Singerian, Lockean, and Leibnizian inquiring systems and Knowledge Management (KM) features. Based on this, the study then proposes a new design for a patient management system in clinics and hospitals.