This paper examines leadership strategies that are most likely to engender success in schools that may be defined as facing challenging circumstances. First, it presents an overview of the relevant literature in order to illustrate distinctive challenges that tend to be encountered in these environments, as well as strategies that are adopted for dealing with such challenges. Secondly, the paper reports on a Western Australian qualitative study of four principals leading primary schools facing challenging circumstances. The paper concludes with a discussion of the implications that may be drawn from the resultant theoretical and empirical insights for policy and practice as well as for future research endeavour.