Knowledge distillation has been widely-used to improve the performance of a "student" network by hoping to mimic soft probabilities of a "teacher" network. Yet, for self-distillation to work, the student must somehow deviate from the teacher (Stanton et al., 2021). But what is the nature of these deviations, and how do they relate to gains in generalization? We investigate these questions through a series of experiments across image and language classification datasets. First, we observe that distillation consistently deviates in a characteristic way: on points where the teacher has low confidence, the student achieves even lower confidence than the teacher. Secondly, we find that deviations in the initial dynamics of training are not crucial -- simply switching to distillation loss in the middle of training can recover much of its gains. We then provide two parallel theoretical perspectives to understand the role of student-teacher deviations in our experiments, one casting distillation as a regularizer in eigenspace, and another as a gradient denoiser. Our analysis bridges several gaps between existing theory and practice by (a) focusing on gradient-descent training, (b) by avoiding label noise assumptions, and (c) by unifying several disjoint empirical and theoretical findings.