The present article addresses the question of whether, and to what extent, critical thinking should make attunement to current social and political landscapes central to its practice. I begin by outlining what I consider to be the basic positions in the debate about the political contextualisation of critical thinking, which are referred to as the crypto-Enlightenment and the critical pedagogical models. I argue, on the basis of various strands of research, that there is a prima facie case to be made in favour of the critical pedagogical position that favours forefronting the social and political context of critical thinking and thinking in general. I then draw attention, however, to problems of coherence and justification in the critical pedagogical position, before turning, finally, to an alternative grounding of critical thinking that takes seriously the historical and social contextualisation of thinking without the coherence problems of critical pedagogy. My conclusion is that while the critical pedagogical model is right to point to the fatal incompleteness of Enlightenment-style critical thinking due to its failure to properly acknowledge the norm-saturated nature of historical consciousness, critical pedagogy itself fails to offer a coherent alternative to the problem of integrating value and rationality in a more full-blown grounding of critical thinking. I suggest that a hermeneutical model that integrates the rational, axiological and historical moments in consciousness provides a more satisfying foundation for understanding the trajectory and purpose of critical thinking.