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The lived realities of agents involved in educational borrowing and change are often omitted as research reside predominantly at a macro level. Using a comparative educational change framework that synthesises concepts in educational change and comparative education, this study examines how ten teachers in Singapore implemented differentiated instruction, an educational approach 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, and how educational change necessitates a comparative and contextually-sensitive lens.