This paper aims to critique and develop neo-Vygotskian work in mathematics education from (i) within the Vygotskian and activity theoretic tradition, and where necessary from (ii) a Bourdieusian perspective. First, I critique Roth and Radford’s (2011) version of Cultural-historical Activity Theory, suggesting that a classroom episode presented as developmental might be seen as a process of alienation. I trace this to the institutional structure of schooling, in which curriculum and pedagogy are alienated from the learner’s everyday sense. Next, I examine and critique the Vygotskian ‘Funds of Knowledge’ approach to critical mathematics education, which seeks to overcome alienation by subjecting the curriculum to the needs of the poor communities the school serves. Here, the critical point on alienation in the Vygotskian approach is better argued in Bourdieu’s perspective on educational institutions as reproductive of class domination. Finally, the paper discusses the extent to which these critiques pertain to Vygotskian activity theory in general or only to these versions in particular and draws implications for the development of a critical mathematics education perspective in a synthesis of perspectives from Vygotsky and Bourdieu.