The mainstreaming of the optional Transition Year (TY) programme in 1994 was a significant innovation in Irish second-level schooling. TY offers schools and teachers extensive freedom to devise imaginative curricula with a particular emphasis on personal and social development and education for citizenship. In this study, an historical perspective identifies ambiguous attitudes to TY since its origins in 1974. The relevant literature on key concepts associated with schools as organisations, educational innovation and resistance, young people’s learning, school leadership and teacher development is reviewed. A central focus of the study involves exploring the attitudes to TY of students, parents, teachers and school leaders using a combination of qualitative and quantitative methods. A consistent pattern through the emerging data is that students are more mature as a result of the TY experience. Young people’s confidence grows, student-teacher relationships are enhanced and opportunities to explore adult and working life are seen as distinct benefits. Individual schools tend to domesticate TY according to their particular histories, traditions, values and contexts. Domestication involves highlighting features of the TY guidelines that fit with schools’ existing identities and neglecting others. The quality of school leadership, particularly by principals and TY co-ordinators, is identified as critically important for effective implementation of the programme. Parents’ attitudes to TY tend to be positive, though they consistently express a desire for more information about the programme. TY’s relationship with other second-level programmes is seen as problematic and significant tensions are identified. The second part of the research involved seeking the perceptions of and attitudes to TY of senior personnel in nine key agencies involved in the making, shaping and implementing of education policy were sought. Discussion resulting from both sets of data examines paradoxical positions where some features of TY are embraced and others resisted. Policy weaknesses are seen as contributing to ambiguous attitudes. Enthusiasm for the innovation is tempered by covert resistance that isolates TY in a type of parallel universe and ensures the hegemony of existing arrangements in schools, notably, the established Leaving Certificate programme and the associated ‘points system’. Current practices which ensure that some young people benefit from six years of second-level schooling and other receive five is seen as unjust and deserving of policy-makers’ urgent attention. Policy implications of the findings, particularly for teachers’ professional development, are discussed.