In recent years, a significant problem that has manifested in the quest to capitalise on the pedagogical potential of technology in schools is that veteran teachers are unwilling to integrate these resources into their practices. Given that veteran teachers comprise up to 40% of teachers, their lack of use is important. This paper aims to shed light on the issue of detachment by presenting empirically based findings of a five-year, grounded theory examination of the technology practices of a small group of veteran teachers. Data included classroom observations, teacher interviews and document analysis of teacher and school planning documentation, student focus groups, interviews with teaching colleagues and key school technology personnel observation. Analysis included the application of the teachers' data to a framework of dilemmas teachers encounter when expected to change their practice. In using this process, change fatigue and knowledge insecurity (brought about by cultural and political changes to their contexts) were prominent factors which contributed to the teachers' lack of technology use. Identifying their challenges opened scrutiny to the myriad of factors they drew on when making decisions about how and whether to use technology in their practice. The longitudinal analysis of the data showed that as these dilemmas alleviated, the teachers became more committed to educational technology. The findings inform how we can move forward from the issue of veteran teachers' lack of use of technology to how to support this group in the development of their practices. In particular, the need for a re-imagining of professional learning to one which focuses on reshaping cultural and political aspects of technology practices. This includes changes to the management of technology-related policy changes as well as facilitating learning communities that promote a valuing and sharing of relevant knowledge amongst teachers and students.