Differentiated instruction (DI) is an effective instructional strategy to maximize individual students’ abilities; in practice, however, its implementation appears to be problematic. To better understand teachers’ perspectives on DI and the effect different teaching contexts can have, we explored teachers’ interactive cognitions of DI in their regular lessons and in “talent lessons.” Four stimulated recall interviews were conducted with a sample of secondary school teachers (n = 4) in the Netherlands. We found that teachers’ interactive cognitions varied depending on the context. More specifically, it appeared that in the “talent lessons,” teachers focused more on small groups or on individual students than they did in the regular lessons. Also, regardless of context, teachers often take student characteristics into account, but how they do this varies among teachers. This study provides a valuable starting point for professional development trajectories and aimed to develop teachers’ implementation of DI while taking individual differences among teachers into account.