More than 20 years after its radical marketoriented reform, the Chilean health care system shows serious equity and fairness problems. Private insurance companies have used ex-ante as well as ex-post risk selection to avoid the affiliation of poorer and older enrolees presenting higher risks. The coexistence of a solidarity-driven public sector and a for-profit private sector operating with risk-adjusted premiums has led to a twotier health insurance system. Unpredictable, often existentially threatening co-payments have become an serious problem for the users of the Chilean health care system, and coverage-lacks have become a major menace for patients. Private insurers supplement "Cream Skimming" and risk selection with contracts calling for significant out-of-pocket payments for health services. This article develops and applies a methodology to measure and compare systematically the impact of user charges for varying levels and complexity of treatment in the public and private health care sector. Co-payments in the private sub-sector show enormous variation, are hyper-regressive and discriminate not only against the ill, but also against the members of the lower socio-economic classes once they have passed the high access barriers. As cost-sharing affects the financial coverage and thus the accessibility of health care, it has become an important mechanism of quality skimping and active disenrolment. Private health insurance companies are relatively well prepared to cover costs for a wide array of traditional health problems; they fail, however, to respond for the costs of other leading diseases in Chile. The private system seems to be poorly prepared to face the challenges of the epidemiological transition in emerging countries.