In university academic advising, identical questions can require different answers depending on a student’s department, admission cohort, and degree program, causing profile-blind retrievers to surface plausible but inapplicable evidence. We present proFILL, a method for transforming hoBIT, our college’s current rule-based advising chatbot, into a profile-aware retrieval-augmented generation (RAG) system. Rather than requiring a complete user profile upfront, proFILL progressively acquires only the profile attributes needed for each query, guided by both the query intent and the initially retrieved evidence, and uses them to condition retrieval over a profile-aware index. Extensive experiments and a human preference study show that proFILL outperforms diverse RAG baselines, is preferred by target users, and remains effective with open-weight models for cost-effective on-premise deployment.

Large-scale introductory CS courses, often enrolling thousands of students, struggle to provide personalized support and encourage active participation. While recent large language models (LLMs) have enabled AI teaching assistants at scale, most existing systems remain reactive, responding only after students explicitly initiate queries. We present SCALA, a student-centered AI learning assistant designed to provide proactive support for students. SCALA introduces predictive query management, a mechanism that generates likely student questions and answers ahead of lectures. Students may choose to view these pre-generated question–answer pairs or engage in interactive conversations with our tutoring model via the same interface. We evaluate SCALA through a semester-long deployment in an undergraduate Python course with over 1,500 students, and find that predictive queries are frequently selected in practice and substantially overlap with real student questions. Based on student feedback, learners preferred SCALA’s responses to their real queries over alternatives such as GPT-4o. These results suggest proactive support as a promising direction for future development of AI-powered teaching assistants. We will release our codebase and interactive demo upon acceptance.