This article proposes a theoretical framework for integrating artificial intelligence with systems thinking to address complex societal and environmental challenges. The framework contrasts two integration approaches grounded in distinct onto-epistemological foundations: one drawing on Martin Heidegger’s critique of technology, and the other on Donna Haraway’s notion of sympoiesis. In the first, AI is understood as the culmination of the technological mode of revealing (Gestell); in the second, it acts as a catalyst for oddkin (unexpected partnerships) and becomes a sympoietic companion to what this paper terms poietic-systems thinking. The paper is structured in three parts. First, it employs a systemic-phenomenological methodology to construct interpretive contextual models that clarify the core conceptions of AI (technological and sympoietic) and systems thinking (poietic-systems thinking). Second, drawing on the author’s research and other scholarly work, it illustrates how each conception of AI can be integrated with systems thinking through concrete examples. Third, it develops theoretical scaffolding that supports these models. Armed with this framework, the paper revisits the initial examples to consolidate a deeper understanding of the two integration approaches. The article concludes with reflections on the education of future systems thinkers, advocating for cultivating capacities suited to sympoietic engagement.