For decades, AI applications in education (AIEd) have shown how AI can contribute to education. However, a challenge remains: how AIEd, guided by educational knowledge, can be made to meet specific needs in education, specifically in supporting learners’ autonomous learning. To address this challenge, we demonstrate the process of developing an AI-applied system that can assist learners in studying autonomously. Guided by a Learner-Generated Context (LGC) framework and development research methodology (Richey and Klein in J Comput High Educ 16(2):23–38, https://doi.org/10.1007/BF02961473, 2005), we define a form of learning called “LGC-based learning,” setting specific study objectives in the design, development, and testing of an AI-based system that can facilitate Korean students’ LGC-based English language learning experience. The new system is developed based on three design principles derived from the literature review. We then recruit three Korean secondary-school students with different educational backgrounds and illustrate and analyze their English learning experiences using the system. Following this analysis, we discuss how the AI-based system facilitates LGC-based learning and further issues to be considered for future research.