The implementation of the Core Tax Administration System (Coretax) has transformed tax administration and reporting mechanisms, requiring taxpayers to strengthen their digital capabilities. An initial assessment of 50 financial staff members at Universitas Negeri Yogyakarta (UNY) identified difficulties in tax reporting. This community service program aimed to improve employees’ literacy and skills in completing and reporting Individual Annual Tax Returns through Coretax while establishing a sustainable assistance mechanism within UNY. The program employed a participatory capacity-building approach and problem-based training through needs identification, initial literacy mapping, socialization, practical training, assistance through the Tax Clinic, evaluation, and institutional capacity strengthening. Assistance was supported by Coretax digital modules, tutorial videos, and self-verification checklists. The results showed that reporting difficulties were related not only to conceptual understanding of taxation but also to procedural skills in using the digital system. A combination of socialization, case-based practice, and individual assistance helped participants understand reporting procedures and resolve technical difficulties. The developed learning media supported independent learning, while strengthening internal tax volunteers and developing standard operating procedures aimed to establish institutional assistance. The program demonstrates that digital tax administration transformation requires stronger tax literacy, digital literacy, and procedural capacity to promote employee independence and sustainable internal support.