Creating and maintaining effective pension regulatory and supervisory structures that secure the interests of the participants and beneficiaries is crucial for systemic stability and economic growth. This paper focuses on the supervision of privately managed, defined contribution pension systems and attempts to clarify key factors that determine the setting and operational activity of pension supervisory structures. Intensity of supervision is measured and compared across a sample of eight countries, using a scoring system that factors in elements that are common to the operational activities of supervision. The results of the exercise show consistent patterns of intensity of supervision activities in relation to the level of economic development, the depth of financial markets, the legal traditions, and the administrative settings of the pension systems in the countries observed. As of yet, there are no best practice models for pension supervision. Nevertheless, consistent supervisory practices can be derived from matching context with supervisory methods to guide policymakers in their decisions.