A Prompt-Engineering Approach to Develop Scalable, Flexible, and Real-Time Hybrid Micro-Level Personalization in a General Purpose AI Teaching Assistant

Education is one of the most promising real-world applications for Large Language Models (LLMs). However, current LLMs rely on static pre-training knowledge and lack adaptation to individual learners, while existing RAG systems fall short in delivering personalized, guided feedback. To bridge this gap, we present DeepTutor, a fully open-source agentic framework that unifies citation-grounded problem tutoring with difficulty-calibrated question generation. A hybrid personalization engine couples static knowledge grounding with dynamic learner memory, continuously adapting each interaction to the student's evolving needs. The same personalization substrate further extends to adaptive learning workflows, interactive books, and proactive multi-channel tutoring agents. To evaluate personalized tutoring, we introduce TutorBench, an interactive benchmark incorporating customized learner profiles grounded in university-level curricula across five domains. We further propose an LLM-based first-person interactive evaluation protocol that conducts assessments via a profile-driven student simulator. Complementary evaluations on established benchmarks, supported by human-alignment and ablation studies, confirm the framework's robustness and general utility. Results show that DeepTutor improves personalized metrics by 10.8% on average and strengthens general agentic reasoning across five backbone models by 29.4%.

LLMs can personalize education, although current static-prompt tutoring systems struggle to adapt to diverse academic disciplines. We develop and test a system with subject-aware prompting, based on 14 pedagogical features (e.g., tutor scaffolding, student understanding) extracted from raw transcripts. We first train a prompt routing model in a simulation environment, and then deploy it for online adaptation with actual high-school students. The simulation benchmark shows the router outperforming two static baselines ($0.694$ vs. $0.647$ and $0.64$, $p<0.001$). A/B testing ($N=656$ conversations from 359 students) shows sim-to-real transfer where the model switches from analytical to scaffolding learning strategies. Our adaptive prompt selection mechanism improves instructional efficiency, maintains pedagogical quality and reduces interactions by around 3 turns ($p=0.007$). While a greedy router achieves a comparable exercise conversion rate with the baseline ($19.1\%$ vs. $19.6\%$), a stochastic router that samples strategies leads to a higher conversion rate ($28.1\%$).

Educators face significant challenges in creating engaging, personalized assignments that accommodate students' diverse interests and cognitive abilities. Traditional one-size-fits-all assignments frequently lead to decreased student engagement and increased reliance on unethical practices such as plagiarism. To address these challenges, we present Taklif.AI, a platform that leverages Large Language Models (LLMs) to automatically generate personalized assignments tailored to individual student interests. Unlike existing AI-powered educational platforms that personalize based on academic performance metrics alone, Taklif.AI incorporates students' extracurricular interests and cultural contexts into the assignment generation process through a structured prompt engineering pipeline with input and output guardrails. The platform employs a serverless architecture on AWS with Next.js, using Llama 3.3 70B as the primary LLM via LiteLLM for multi-provider load balancing and LangChain for prompt orchestration. We describe the system architecture, the prompt design methodology, and the guardrails framework that ensures output quality. Preliminary user acceptance testing with 68 participants (65 students and 3 educators) indicates positive reception, with 84% of participants rating the personalization feature as beneficial. We discuss the platform's current capabilities and limitations, and outline directions for rigorous empirical evaluation of learning outcomes.