Limited research has been conducted into the teaching primary principalship in Australia, as the focus has tended to be on full time school principals. It has often been assumed that the principalship role in smaller primary schools is a ‘scaled down’ version of a full time primary principalship and that similar leadership and management challenges apply. There is limited recognition of the unique challenges of teaching primary principals who have the dual roles of school management and classroom teaching responsibilities in devolving school systems. A mixed method research design was developed to explore the current issues, challenges and concerns of teaching primary principals in three school systems in New South Wales. In-depth interviews with teaching primary principals informed the development of a Teaching Primary Principals Perception Survey (TPSPS) which was forwarded to Department of Education and Training, Catholic and Seventh-day Adventist teaching primary principals in New South Wales. This paper explores the issues challenges and concerns of teaching primary principals in New South Wales and provides recommendations to address challenges associated with the dual role of teaching and leading a small primary school.