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Teachers are pivotal to the success of educational change. Yet, when reforms involving educational ideas borrowed from abroad are introduced, rarely do we pay attention to how context shapes teachers’ learning, perception, and implementation of ideas from abroad. Using a qualitative comparative approach, I analysed data from two qualitative studies around Singapore teachers’ perceptions and implementations of DI to distil how contextual elements shape teachers’ interactions with new educational ideas. Findings reveal that when teachers encounter differentiated instruction, issues related to sociocultural, political, technological, and postmodern perspectives surfaced. This suggests a need for enhanced sensitivities towards and unpacking of educational approaches—in professional development and support for teachers—that foregrounds contextual variances.