There has been longstanding debate about whether the level of complexity of questions received at reference desks and via online chat services requires a librarian's expertise. Continued decreases in the number and complexity of reference questions have all but ended the debate; many academic libraries no longer staff service points with professional librarians. However, convenient, proactive online chat services could reverse the trends. This paper provides results of a study of reference question complexity following implementation of a proactive chat service. The study reveals changes in the complexity of chat questions that may have implications for staffing online reference services.oincident with the rise of information literacy efforts and the simplification in the online environment, there has been a dramatic decrease in reference questions. According to ACRL's Academic Library Statistics, the number of reference transactions in doctorate-granting institutions declined 49 percent between 2000 and 2012, and nearly all the questions that remain are directional, basic search questions and questions related to library operations.1 These point-of-need questions, regardless of the medium over which they are conducted, served multiple purposes. At the most basic level, they provided support for the mechanics of library research, helping users navigate multiple information silos and the physical organization of the library. Although, on the surface, support for these questions related to the mechanics of library research, they also provided an opportunity for broad research support. The librarian had sufficient knowledge of the curriculum, the publication patterns of disciplines and subjects, and thesis and topic development to provide broad research support. In the case of student researchers, the librarian had the opportunity to reach the student at a teachable moment, reinforcing course content, guiding the student in formulating a research topic that was practical and appropriate for the given assignment, and then providing guidance in evaluating sources. The components of the reference transaction-support for the mechanical aspects of library research and the broader research expertise-were so tightly interwoven that many librarians assumed that, if information literacy instruction were integrated into the curriculum, doi:10.5860/crl.76.7.959 crl15-725