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Educational technology's role in supporting Self-Regulated Learning (SRL) and Adaptive Learning Technology's (ALT) personalized assistance for learners are growing. Leveraging context-aware user data collection in technology-enhanced learning shows promise, but addressing pedagogical concerns throughout the learning-teaching process remains challenging. Learners may perceive ALT as not tailored to their needs, impacting their attitudes towards these systems. This study investigates the potential of combining Natural Language Processing (NLP) with ALT to enhance real-time contextual adaptive learning for SRL support. Through a one-year co-design phase with a high school, we developed and evaluated the ALT, finding positive reception. Integrating NLP and ALT offers promising future enhancements for sustainable SRL support.