Abstract. Critical thinking skills among students (santri) in Islamic boarding schools generally remain limited, partly due to the continued dominance of rote-memorization methods that leave little room for independent analysis. Meanwhile, amid the massive flow of digital information, santri are expected to filter and critically assess the validity of ideas independently. This study aims to describe the planning, implementation, and evaluation of the Bahtsul Masail program and its impact on students' critical thinking at Al-Istiqlal Tanimulya Islamic Boarding School. A qualitative case study approach was employed. Four informants were purposively selected, consisting of the pesantren caretaker, a mushohih (validating teacher), and two santri with differing educational backgrounds and lengths of involvement. Data were collected through in-depth interviews, observation, and documentation, then analyzed using the Miles and Huberman interactive model. The findings show that program planning is built upon an orally transmitted intellectual tradition rather than formal written documents, covering the formulation of objectives, themes, role distribution, and a tiered system of classical-text references. Implementation follows the stages of muqaddimah, shifatus su'al, ta'bir, i'tirodl, and tashih, which consistently train students' analytical and argumentative skills. Evaluation is conducted through direct observation without a standardized written instrument, emphasizing depth of reasoning over frequency of speaking. The program is shown to gradually shift students' critical thinking from the reception stage toward comprehension, analysis, evaluation, and eventually approaching critical creation, in line with the duration of involvement and mastery of supporting linguistic tools. Keywords: Bahtsul Masail, Critical Thinking, Islamic Boarding School Abstrak. Kemampuan berpikir kritis di kalangan santri pesantren pada umumnya masih tergolong rendah, salah satunya disebabkan oleh dominasi metode pembelajaran hafalan yang belum banyak melatih daya analisis mandiri. Padahal, di tengah derasnya arus informasi digital, santri dituntut mampu menyaring dan menilai kebenaran suatu gagasan secara mandiri. Penelitian ini bertujuan mendeskripsikan perencanaan, pelaksanaan, dan evaluasi Program Bahtsul Masail serta dampaknya terhadap peningkatan daya kritis santri di Pondok Pesantren Al-Istiqlal Tanimulya. Pendekatan yang digunakan adalah kualitatif dengan jenis studi kasus. Empat informan dipilih secara purposif, terdiri atas pengasuh pesantren, seorang ustadz mushohih, serta dua orang santri dengan latar belakang pendidikan dan lama keterlibatan yang berbeda. Data dihimpun melalui wawancara mendalam, observasi, dan studi dokumentasi, kemudian dianalisis dengan model interaktif Miles dan Huberman. Hasil penelitian menunjukkan bahwa perencanaan program dibangun dari tradisi keilmuan yang diwariskan secara lisan tanpa dokumen formal, meliputi penetapan tujuan, tema, pembagian peran, serta penjenjangan referensi kitab kuning. Pelaksanaannya berlangsung melalui tahapan muqaddimah, shifatus su'al, ta'bir, i'tirodl, hingga tashih, yang secara konsisten melatih kemampuan analisis dan argumentasi santri. Evaluasi dilakukan melalui pengamatan langsung tanpa instrumen tertulis baku, dengan penekanan pada kedalaman nalar dibandingkan intensitas berbicara. Program ini terbukti mendorong pergeseran bertahap daya kritis santri, dari tahap penerimaan menuju pemahaman, analisis, evaluasi, hingga mendekati kreasi kritis, sejalan dengan lamanya keterlibatan dan penguasaan ilmu alat santri. Kata Kunci: Bahtsul Masail, Berpikir Kritis, Pesantren