The lived realities of agents involved in educational borrowing or transfer are often omitted as research and discussions reside predominantly at a macro level. Through the lens of a comparative educational change framework synthesising concepts in educational change and comparative education, this study examines the lived experiences of teachers in Singapore implementing differentiated instruction, a form of learner-centred education, borrowed from the U.S. Interviewing and observing teachers, we found that they experienced postmodern and political tensions around sociocultural expectations of teaching, learning, and learners. Simultaneously, they struggled with technological considerations like structural conditions in schools and insecurities around their competencies. These findings spell implications for how we support teachers involved in educational borrowing professionally, intellectually, and emotionally. Educational borrowing on the ground can benefit from the consideration of technological, sociocultural, political, and postmodern perspectives of educational change.