This paper explores an innovative assessment approach designed for master-level students enrolled in a Communication and Technologies program, and it addresses the challenges posed by the use of generative AI tools in higher education settings. Rather than prohibiting the use of AI, we developed “Devil’s Advocates Wear AI” (DAwAI), a novel activity and assessment method that deliberately incorporates AI in an assistive role while ensuring authentic learning. DAwAI adapts the “think-pair-share” pedagogical strategy into a semester-long exercise where students first independently develop reflective learning journals on course topics, imagining positive future applications in their careers. Subsequently, each student anonymously critiques the work of one peer, supported by AI tools which help them identify unconsidered perspectives, whilst having to document their prompting strategies and AI interactions. The approach concludes with revealing identities and sharing all reflections with the class. This methodology promotes continuous engagement with course content, develops critical thinking and futures literacy, teaches responsible AI utilisation, and reduces opportunities for academic misconduct by emphasising personal reflection. Preliminary observations indicate strong student engagement, particularly among technically inclined participants. The assessment demonstrates how AI can serve as a meaningful dialogue partner in education, transforming evaluation into an integrated learning opportunity rather than merely an end-point measurement. Future research will compare experiences across different student populations and analyse the complementary use of visual elements observed in submissions.