Pembelajaran sejarah di tingkat sekolah menengah sering kali terjebak pada metode hafalan pasif, yang menyebabkan rendahnya kemampuan berpikir kritis dan minimnya empati historis siswa. Kegiatan pengabdian masyarakat ini bertujuan untuk mentransformasi pembelajaran sejarah di SMA Katolik Santo Yusup Surabaya melalui implementasi platform asisten virtual berbasis Artificial Intelligence (AI) bernama "Kak Sarah". Platform ini dikembangkan menggunakan model Successive Approximation Model (SAM) yang terintegrasi dengan Design Thinking, memanfaatkan teknologi Retrieval-Augmented Generation (RAG) untuk menyajikan simulasi peran naratif dan dialog sokratik yang akurat. Implementasi dilakukan melalui pelatihan guru dan uji coba langsung di kelas yang melibatkan siswa kelas XI. Hasil evaluasi menunjukkan dampak signifikan, di mana rata-rata nilai kemampuan berpikir kritis siswa kelas eksperimen meningkat drastis dari 53,22 (pre-test) menjadi 88,06 (post-test). Peningkatan ini jauh melampaui kelas kontrol, dengan signifikansi statistik (p=0,005). Selain aspek kognitif, validasi ahli materi dan media mengonfirmasi kelayakan platform sebagai media pembelajaran adaptif. Program ini berhasil menjembatani kesenjangan teknologi di sekolah mitra dan menciptakan pengalaman belajar sejarah yang mendalam (deep learning) serta menyenangkan. Abctract History learning at the secondary school level is often trapped in passive rote memorization methods, leading to low critical thinking skills and a lack of historical empathy among students. This community service activity aims to transform history learning at SMA Katolik Santo Yusup Surabaya through the implementation of an Artificial Intelligence (AI)-based virtual assistant platform named "Kak Sarah." The platform was developed using the Successive Approximation Model (SAM) integrated with Design Thinking, utilizing Retrieval-Augmented Generation (RAG) technology to present accurate narrative role-playing simulations and Socratic dialogues. Implementation was carried out through teacher training and direct classroom trials involving 11th-grade students. Evaluation results showed a significant impact, where the average critical thinking score of experimental class students increased drastically from 53.22 (pre-test) to 88.06 (post-test). This improvement far exceeded the control class, with statistical significance (p=0.005). In addition to cognitive aspects, validation from subject matter and media experts confirmed the platform's feasibility as an adaptive learning medium. This program successfully bridged the technological gap at the partner school and created a deep, enjoyable history learning experience.