Career indecision among Madrasah Aliyah graduates remains a persistent problem in Indonesian secondary education. This problem is further complicated in schools that combine a general curriculum with pesantren (Islamic boarding school) routines. This study examines the implementation of specialization guidance (layanan peminatan) within the guidance and counseling program at MA Matsaratul Huda, Pamekasan, and its impact on students’ career planning readiness. A qualitative descriptive design was used, involving 12 informants: the school principal, five teachers (including the guidance and counseling teacher, subject teachers, and homeroom teachers), and six twelfth grade students who had participated in the specialization service. Data were collected from 2 to 29 July 2026 through observation, semi structured interviews, and documentation, and were analyzed inductively through data reduction, display, and conclusion verification, with credibility strengthened through prolonged engagement and triangulation across observation, interview, and documentation sources. Findings show that specialization services combined classical and individual strategies, integrating formal in class sessions with informal approaches, and drew on report card achievement, psychological observation, and students’ self reported interests as assessment instruments. According to informants’ accounts, the service was perceived to strengthen self understanding, reduce confusion in choosing further education, and build confidence through sustained teacher support, with success also reflected in several students’ university admission outcomes. Supporting factors included institutional commitment, parental involvement, and dedicated facilities; inhibiting factors included pesantren schedule conflicts, distance related parental restrictions, and an unintegrated formal schedule. These findings extend trait and factor and career development perspectives to the pesantren based madrasah context, with implications for Islamic career guidance practice.