After its founding in 1985 and subsequent multiple changes in leaderhip, Taiwan's National Health Insurance, NHI, finally underwent full reform in 2013 to yield its current second Generation Policy. NHI not only has gained international prominence, but also has achieved incredibly high rates of satisfaction and is often cited as a miracle in nationalized health insurance models. However, its compulsory single-payer plan has drastically affected development of the medical industry. Most prominently, as new medical graduates move towards fields such as Ophthomology, Dermatology, and Aesthetic Medicine that offer higher reimbursement to workload ratios, specialities including Internal Medicine, Surgery, Obstetrics and Gynecology, Pediatrics, Emergency Medicine, and Anesthesiology are becoming unsuccessful in recruiting a new generation of medical providers. Using document analysis,this paper focuses on how NHI has affected the field of Anesthesiology, particularly looking into data and analyses pertaining to anesthiology personnel (anesthesiologists and nurse anesthetists), workload, salary, quality, and medical malpractice. Results show insufficiency in anesthesiology personnel, 60-hour week workload per anesthiologist who staffs four operating rooms, salary less than half of what similar practitioners in the US receive, poorer anesthetic quality with a 24-fold higher anesthesia-related mortality when compared to US practices and 12-fold higher when compared to Japanese practices, and both higher likelihood of and payout for medical malpractice compared to other medical fields. In light of such issues, the solution lies in yet another complete reform of NHI – abolishing the current payment system based on case number and anesthetic type and replacing it with one based on patient’s physical status. Furthermore, Nurse anesthetist personnel training also needs to be reformed, pursuing a model similar to that of the US while clearly outlining the field’s procedural boundaries. In addition, the Taiwan Society of Anesthesiologists also needs to play a more prominent role in quality assurance, as well as in aiding practitioners navigate dispute issues. All of these changes will be instrumental to improving the current state of Anesthesiology in Taiwan.