This article reports research from a qualitative case study of three preservice English teachers who participated in the Web Pen Pals project, a university--secondary telecollaborative partnership which paired preservice English teachers enrolled in the author's young adult literature course with local middle school students in online chat rooms to discuss young adult literature. The goal of the project was to help preservice teachers learn how to facilitate literature discussions from a critical literacy stance. This article reports findings from analysis of the questioning strategies one preservice teacher used to facilitate critical talk online with adolescents. Findings suggest preservice teachers can bring traditional expectations for discussion to the CMC environment that work against the goals of critical literacy. Implications for future instruction are shared. (Contains 3 tables and 1 figure.)