The social model of disability, accessibility legislation, and the digital transformation spurred by COVID-19 expose a lack of accessibility capacity in the workforce, indicating persistent gaps in academic and professional education. We adopt a socio-cultural lens to examine how the context of education and training influences teaching and learning in university and workplace sectors, and how expert educators manage and negotiate these contextual factors to build accessibility capacity. This paper reports qualitative research with 55 experienced educators using expert panel method and focus groups. Analysis highlights the important disconnects and contextual challenges that educators must navigate and negotiate to affect and embed cultural change. We find that faculty and workplace cultures frequently perpetuate precarity in accessibility education, individualising the responsibility to ‘heroes’ or ‘champions’, while disciplinary and role-based silos limit the scope for raising awareness and developing widescale competency. Conversely, centres of excellence and communities of practice can cultivate and sustain links between education and research, engage expert users, and promote interdisciplinary and cross-role learning environments, where accessibility is increasingly recognised as a shared endeavour. We conclude that greater collaboration between academia and industry can enhance pedagogical understanding, to transform accessibility educational practices and build and sustain capacity for the future.