Literacies are always learned in particular social places and spaces, and the nature of a site shapes the experiences people have of learning literacies there. This paper considers the experiences of staff in two contrasting workplaces: an early years centre, and an adult education college. Both are educational workplaces, and staff are engaged in extensive literacy practices relating to recording and accountability, which they colloquially term ‘the paperwork’. In both sites, this paperwork is a source of struggle. However, closer analysis based on interviews and observations showed that there were significant differences between people’s experiences of learning accountability paperwork practices in the two sites. The paper identifies the key characteristics of these sites which seemed to foster or discourage the development of ‘mastery’ or ‘skilled knowledgeability’, drawing on situated learning theory. These site-specific characteristics are related to the broader processes of commodification of education within which the sites are situated.