The emergence of Generative Artificial Intelligence (GenAI) technologies is transforming the epistemological and operational foundations of educational assessment, particularly within adult learning contexts. This chapter explores the pedagogical, ethical, and infrastructural implications of integrating GenAI into adult education systems across Southeast Asia. Drawing on contemporary theoretical frameworks—ranging from andragogy and transformative learning to critical digital pedagogy—it critically examines how GenAI reshapes assessment logics, redistributes epistemic authority, and reconfigures learner agency. Through a contextual lens, the chapter interrogates regional disparities in policy governance, digital infrastructure, educator readiness, and cultural alignment. Five interrelated domains are analyzed: governance fragmentation, infrastructural inequalities, programmatic integration, digital literacy and ethics, and strategies for inclusive innovation. While GenAI holds potential to enhance personalization, adaptivity, and reflective assessment practices, its effective implementation demands a paradigm shift in both pedagogy and policy. The chapter advocates for an ethically grounded, equity-driven, and context-responsive approach to AI adoption—one that foregrounds human-centered learning and regional diversity. Ultimately, it positions GenAI not as a panacea, but as a sociotechnical mediator whose impact must be shaped by inclusive governance, critical pedagogy, and participatory educational design.