This article explores four essential questions that have emerged from recent case law governing fiduciaries. The questions raised form a composite inquiry into fiduciary regulation. Firstly, is there a shift in the fiduciary paradigm? The courts have shown an eagerness to test the boundaries of the fiduciary status, both in expanding and withdrawing the status for different appointments. Secondly, is there an expansion of fiduciary duties beyond the “no-conflict” and “no-profit” duties? Thirdly, what is the “irreducible core” – if any – of fiduciary obligations? This article contends that fiduciary duties can be classified into “selflessness oriented” and “competence oriented” duties, with the former constituting the “irreducible core”. Lastly, what are the exceptions to the “non-intervention” principle? The courts normally accord a wide margin of appreciation to a fiduciary’s exercise of discretion. Besides the “breach of fiduciary duty” exception, this article suggests that equity can draw inspiration from administrative law in the regulation of public officials.