Doing and teaching critical literacies (CL) is complex, unpredictable work. In this article, we explore an unexpected turning point, and "teachable moment", with postgraduate students in a South African university. We focus on a redesign task created to scaffold postgraduate students' developing understanding of critical literacy theory and research into contextually applicable praxis. However, the cohort which this study is based on struggled to master key concepts and make the move toward praxis. At this juncture, of struggle and problem-solving, we (lecturers, researchers, tutors, and students) encountered collaboration as a turning point in doing redesign as a critical-creative-affective practice. A critical analysis of lecturer/tutor reflective vignettes of pedagogy and space, students' collaborative, multimodal redesigns of a university advertisement, and semi-structured focus groups with students reveals the "conditions of possibility" enabled by collaborative redesign. We present a multivoiced case study and discuss three main findings: (1) collaboration, negotiation, and discussion as critical-creative-affective practices in redesign, (2) the role of safe space(s) for promoting students' grappling with CL as praxis, and (3) students' discursive-material design of (hyper)inclusivity. Overall, we argue that a key contribution of this article is a nuanced understanding of the role of collaboration and dialogue in CL pedagogy, extending conceptualizations of dialogue/dialogic in critical literacies. That is, there is a need for dialogue as both critical-creative-affective exploration with text and meaning-making that is contingent on the nature of classroom space. We conclude with educational implications which are highly specific practices, tools and principles embedded in the case study that can be (re)imagined and adapted for a range of (literacy) contexts, while the detail and depth of the case study provides a vivid account of what this means in practice.