This study aims to explore pupils' affective engagement with school and music during their transition to secondary school. A gender comparison is also being made to ascertain any differences that may exist between boys and girls during this time. A sample of 182 pupils completed two questionnaires (attitudes to school and attitudes to music) three times (at the end of Year 6, at the beginning and end of Year 7). A series of one-way repeated measures analysis of variance tests showed that pupils' overall attitudes to school dropped significantly from the end of Year 6 to the end of Year 7 with their enjoyment towards school and their satisfaction with the work environment declining. Pupils' attitudes to music presented a significant fall at the end of Year 7 after a slight improvement at the beginning of secondary school. Girls held consistently more positive attitudes towards school and music than boys. It is suggested that pupils' attitudes are malleable and responsive to environmental change and, therefore, this problem can be remedied if appropriate interventions are put into place particularly regarding the teacher-pupil relationship and pupils' perceived autonomy in their learning.