This chapter explores the evolving relationship between humans and artificial intelligence (AI) as partners in learning. Grounded in Douglas Engelbart’s vision of man–machine symbiosis, we outline the development of AI-powered learning systems capable of personalizing feedback, adapting to cognitive states, and enhancing knowledge retention. In addition to these promises, the chapter critically examines the risks our current technology landscape poses to learners, such as device dependency, information overload, distraction, and cognitive manipulation. In response to these challenges, the chapter challenges designers and creators of information systems to prioritize deep engagement, learner autonomy, and critical reflection. Shifting from passive information consumption to active knowledge construction is a prerequisite for a future in which AI systems are not just tools of efficiency, but trusted partners in our lifelong learning journey.