The global spread of digital learning indicates a degradation of the current traditional teacher-centred approach to schooling, replaced by a form of teaching and learning where digital education leads personalised learning (Benade, 2015). As the digital age continues to shape the context of modern education, scholars are exploring new ways of bridging Western and Eastern perspectives on education in order to better understand the role of critical pedagogy today. Freire’s (2021) critical pedagogy emphasises that traditional forms of education tend to reinforce educator power structures, which may trigger inequalities. Critical pedagogy can promote the idea that education should be a process that liberates the capacity to learn rather than a merely mechanical means of imparting knowledge or skills. Eastern Confucianism, represented by Confucius (770–481 BCE), pointed to the importance of moral behaviours, such as 'Jen'(Benevolence), 'Li’ (Ritual), and 'Zhi'(Wisdom), which emphasised the role of the teacher in society (Tan, 2015). Thus, Paulo Freire's critical pedagogy and Confucianism both offer unique perspectives on ways to re-imagine education in the digital age (Freire, 2015; Tan, 2015). This paper explores how the educational theories of two philosophers from the East and West, Confucius and Paulo Freire, as can offer a critical understanding of digital education.