Learner-centred educational approaches, like differentiated instruction (DI), have been gaining popularity worldwide through the process of educational borrowing. Teachers' experiences with educational change are complicated when the educational ideas they encounter are transferred from abroad. This mixed method study examined how ten teachers in Singapore implemented and experienced DI, an educational approach from the USA. Findings revealed that when the destination conditions are more aligned with source conditions, Singapore teachers experience greater successes in their DI implementation, specifically in creating environments that support learning, building on quality curriculum, and leading and managing the classroom. When teachers faced cultural, technological, and political misalignments, they encountered greater obstacles, specifically, in using assessment and adapting instruction to student variances. Findings spell implications for greater synergy across educational change and borrowing work, including more criticality when borrowing educational ideas across countries and the need to foreground contextual peculiarities in both source and destination countries.