This article addresses the challenges of supporting students' engagement with complex, challenging texts. How do teachers sustain students' interactions with texts that many see as irrelevant to their lives? How do they provide space to name and challenge the simplistic or problematic portrayals of cultures and communities often found in the texts we are required to teach? In this article, the author presents answers to these questions with the belief that these obstacles are worth overcoming. The author details three activities that have helped her support students in understanding; engaging with; and critiquing complex, challenging texts: guided role-play, a prereading activity that helps readers activate relevant prior knowledge; points of contact, an activity used to highlight and raise questions about textual biases; and collaborative reenactments that support readers in bringing character interactions to life. (Contains 3 figures.)