Building on recent efforts to bridge transformative learning and world language education (Clifford & Reisinger, 2019; Johnson, 2015; Randolph & Johnson, 2017), this article explores how perspective-shifting can be fostered among L2 learners through critical reflection tasks staged across collegiate language curricula. A range of reflection tasks designed to decenter the self from existing assumptions, beliefs, and values as learners try on and respond to cultural perspectives different from their own is presented, focusing on the developmental needs of learners at different instructional levels. The study investigates how beginning to advanced collegiate L2 learners perceive working with structured reflection (SR) tasks across two German programs in the United States (an R1 state university and a private liberal arts college). Analysis of student surveys (n = 237) shows that L2 learners largely valued doing reflective work and that some learners found SR helped them to think about and evaluate their learning and facilitate perspective-shifting.