This article employs Rittel and Webber's "wicked" problem as a heuristic device for enhancing understanding about National Assessment Program--Literacy and Numeracy (NAPLAN) testing in the Australian education context. Using a research project with seven independent schools in New South Wales, Australia, which analysed NAPLAN data from primary (elementary) students in years 3 and 5, this article highlights the "wicked" nature of the problem of NAPLAN testing, and standardised testing more generally. The research project, as a catalyst for the article, evidenced a set of difficulties, particularly for smaller primary schools, and highlighted the ways in which these schools experienced many of the challenges that the literature indicates are evident in the current regimes of standardised testing. The article focusses on problematising NAPLAN's use in Australia and uses the literature to critique its application. It then outlines Rittel and Webber's criteria that determine whether a problem might be "wicked" and applies this as a lens for considering NAPLAN testing. In problematising NAPLAN testing and applying wicked problem theory to the issue, this article asserts that many of the challenges can be managed and indeed may empower and liberate stakeholders.