This paper examines the history of epistemological conceptualizations of the library, considered
as a technology. Drawing from Heidegger’s philosophy, a technology is a way of human relating to the world. At its best, this relationship is in terms of belonging and understanding, but modern information technologies may not foster such aims very well. Heidegger links understanding to questioning; thus, this paper paper explores questioning in the library as a path to reorient the library more concertedly toward understanding. As a first stage in such work, this paper explores the history of questioning in the library. The library was originally conceived as an educational institution that afforded questioning, personal relationships and understanding. As time wore on, the library was transformed into something more like a business, where answers and information were provided as economic resources. This paper provides grounds for a renewed conceptualization of the library as a site for understanding and questioning. If the field is to reorient toward understanding, a deeper appreciation for questioning will be required.