When structured effectively, online discussions can create safe and brave spaces (Murphy et al., 2020) for students to engage in meaningful dialogue surrounding traditionally difficult topics, like gender and sexuality. Yet it can be challenging to motivate students to participate in online discussions (Moore, 2021). In this chapter, we show how the #digitalpowerups strategy provides an innovative and effective way for instructors to engage students in higher-order online discussion by developing Habits of Mind skills, such as applying past knowledge to new situations, thinking about your thinking (metacognition), listening and understanding with empathy, thinking interdependently, responding with wonder and awe, and striving for accuracy (Al-Zakri & Al-Jubair, 2020; Costa & Kallick, 2009).