Pesantren is one of the Islamic educational institutions that has an important role in character building and community diversity. In managing pesantren finances, the implementation of technology is crucial to improve effectiveness and efficiency. One of the innovations adopted is the cashless payment system, as carried out by Pondok Pesantren Nurul Jadid Paiton Probolinggo through the e-Bekal Santri NJ application. Although it provides various benefits, the use of cashless payment is still faced with various challenges, both from internal and external pesantren. The programme evaluation shows a diverse response from various related parties, ranging from santri guardians who appreciate the ease of monitoring to cooperative guards who experience technical difficulties. Renewal and improvement of application features are needed to improve the transaction process and increase the acceptance of cashless technology in the pesantren environment. This research uses a qualitative descriptive approach to explain the cashless payment implementation mechanism at Pondok Pesantren Nurul Jadid, highlighting the important role of financial management in dealing with financial risks and utilising technology in the Society 5.0 era.