The High Court’s 1998 decision in Project Blue Sky Inc v Australian Broadcasting Authority, with its close attention to specific statutory context and purpose, has had an important influence on Australian administrative law. Not least, it appears to have led to some “repatriation” of freestanding standards of administrative legality. Yet close analysis reveals that this evolution is best understood as part of broader dynamic, namely a two-stage search for flexibility in judicial review principles – in response to changing contexts and new challenges. The first stage has seen some careful calibration of principle to statutory context, and the second a calibration to consequence (as reflected in the new “materiality” overlay in jurisdictional error doctrine). This search for flexibility builds agility into the principles but appears to come at some cost – including to the consistency, predictability and normative influence of administrative law. These evolutions, and the attending dilemmas, warrant close consideration as Australian administrative law has perhaps found itself at a new crossroads.