In response to growing diversity in school and the need for a future-ready educational system, the Ministry of Education (MOE) has prioritised differentiated instruction (DI) as one of six areas of practices Singapore teachers are encouraged to learn. Against this background, this study uses a qualitative comparative approach to perform a secondary analysis of data from two qualitative studies: one on Singapore teachers’ perceptions and the other on their implementations of DI. Findings reveal teachers’ concerns clustered around sociocultural, political, technological, and postmodern issues as they grapple with DI, an educational approach borrowed from the U.S. Participants’ perceptions and implementations point to the complexities involved in learning educational ideas arising from contexts that hold different assumptions around teaching, learning, and students, and that are structured differently. Findings spell implications on how ideas accompanying educational change need to be analysed and localised to enhance teachers’ learning and practices, as well as how professional development, educational structures, and support for teachers need to be refined to account for contextual variances.