In this article, I examine a public-private partnership project in West Bengal, India, that trains and deploys people from marginalised castes as digital health workers in rural areas. Although digital technologies offer new opportunities for access to the medical sector, caste hierarchies inherent to the field persist, reinforcing and perpetuating caste-based inequities. This is evident in the division of labour, shaped by caste dynamics and justified through the distinction between professional knowledge and technical skill. The widely-used metaphors of the doctor—and by extension the software—as the mind, and the health workers as foot soldiers, rely on and further entrench long-standing hierarchies of expertise where privileged castes do knowledge work while marginalised castes literally do the footwork. Nevertheless, health workers actively challenge these hierarchies and foreground their creative contributions. While caste lives on in projects of ‘empowerment’, particularly through the limited and limiting imaginations of health workers’ structural position, health workers find ways to visibilise and value their labour and expertise. I argue that their assertions and aspirations may open up new possibilities for thinking about ‘empowerment’. Overall, recast(e)ing medicine implies that caste in the health sector is being simultaneously perpetuated and reimagined in ambivalent and partly contradictory ways.