Generational change is believed to be transforming the educational and employment preferences of medical trainees. In this article, we examine generational tensions in interviews with policy leaders and clinicians on workforce issues within one subset of the Australian medical profession: general practitioners who provide care to people with HIV in community settings. Integrating the accounts of policy leaders (n = 24) and clinicians representing the ‘first generation’ (n = 21) and ‘next generation’ (n = 23) of clinicians to do this work, shared and divergent perspectives on the role of generational change in shaping professional engagement were revealed. While those engaged in the early response to HIV believed younger clinicians to be less interested in the scientific and political dimensions of HIV care and more concerned about financial security and life balance, the next generation both countered and integrated these beliefs into new ways of conceptualising the value and appeal of this field of medicine. Critical appraisal of the assumptions that underpin generational discourse is essential in appreciating the changing views of providers over time, particularly in fields of medicine which have featured significant historical turning points.