The aim of this paper is to revisit Husserl and Dilthey’s 1911 correspondence in order to develop a deeper perspective on a tendency in critical phenomenological research: the tendency to historicize lived experience. I argue for two theses: first, while both Husserl and Dilthey recognized that lived experience is always historically situated, they diverged in their approaches to the interpretation of historicity—Husserl adopting a transcendental approach, and Dilthey a hermeneutic approach. Second, while Husserl’s treatment of historicity is in tension with critical phenomenology’s commitment to historicizing the phenomenological attitude itself, Dilthey’s treatment suggests that our historicity needs to be interpreted as something that is itself socially and historically conditioned. For this reason, Dilthey’s attempt to achieve a hermeneutic conception of understanding offers insight for critical phenomenology’s treatment of the relationship between phenomenology and history.