This paper examines the advertising risk-taking propensity of not-for-profit organisations (NFPs) – a sector of growing economic and social importance. Much of their advertising over the past few years has been risky and controversial. The question as to why this has happened is framed within the strategic and advertising risk literature. Evaluation of data from a mail questionnaire found that hardly any of the leading paradigms fit the NFP sector. A variety of explanations are offered based upon the nature of the NFP organisation and potential weaknesses in theory. Managerial implications and possible avenues for future research are offered.