The phenomenon of understanding lies at the heart of the qualitative inquiry enterprise. Drawing on the tradition of philosophical hermeneutics, this article discusses the following four conditions under which understanding unfolds: (a) the difference between knowing and understanding; (b) understanding as learning rather than reading; (c) understanding as relational and hence requiring openness, dialogue, and listening; and (d) understanding as entailing the possibility for misunderstanding. The article closes with some brief comments on the implications of this investigation for what it means to be a qualitative inquirer.