The concern in Australia about boys and girls leaving school early has become prominent in social, political and educational arenas over the past two decades. The Apparent Retention Rate (ARR) to Year 12 indicated that in 2002, 19.3% of females and 30.2% of males left before completing Year 12 in Australian schools (Commonwealth of Australia 2003). Despite the steady rise in completion rates for boys, the ARR of 69.8% in 2002 is deemed to be low considering that the successful completion of Year 12 has important benefits to students. How well Australian boys perform during the compulsory years of schooling has generated consistent interest from academics, school personnel and state education departments alike. Considerable research nationally (Ball & Lamb 2001; Collins et al. 2000; Lamb et al. 2004, McMillan & Marks 2003) and internationally (Arnot et al. 1998, 1999; Cullingford 1990, 1999, 2002; Erskine 1999; Fine 1991) has highlighted that boys experience problems at school in terms of learning, behaviour, achievement and participation when compared to girls. In particular, the retention of boys to Year 12 has been problematic. This paper reports on themes identified as common with 22 school leaving boys from three different social contexts – provincial, rural and metropolitan – and two sites were chosen from each social context. Analysis of the themes will provide greater clarity to what motivated their early school leaving decisions.