Secondary students are often challenged to make sense of conceptually complex content area texts. Text-based discussion has the potential to facilitate comprehension by engaging students in collaboratively constructing their understanding of important ideas and relationships among ideas while interacting with a demanding text. However, teachers often find it difficult to construct prompts for discussion that effectively facilitate deep thinking. This article describes a professional development process in which middle and high school teachers analyzed texts and prepared plans with prompts to facilitate thinking in the context of text-based discussion. Teacher responses to this experience included (a) implementing the planning process using strong disciplinary knowledge, demonstrating student learning; (b) striving to create a thoughtful discussion plan while balancing competing demands for instructional focus, (c) constrained by required, low-quality curricular materials; and (d) contesting the demands of the professional development experiences.