Digital services have increased muzakki expectations for zakat reports that are open, easy to access, and verifiable. This change creates a challenge for traditional pesantren, which have long relied on trust in the kiai and administrators. This study explains the relationship between trust and administration in zakat reporting, identifies the institutional pressures that encourage change, and develops a digitalization framework suited to the pesantren context. The study used a qualitative single-case design at a salafiyah pesantren in West Java. The main data came from an in-depth interview with one key informant and were checked through observations of recording practices and reviews of cash-report drafts and transaction receipts. The data were analyzed thematically using Institutional Theory, Stewardship Theory, and the Technology–Organization–Environment (TOE) Framework. The findings show that administration is not viewed as replacing trust. Financial records are understood as part of hisab, a way to protect the institution’s good name, and evidence of responsible fund management. Mimetic pressure, or the push to follow more transparent and digital zakat institutions, was perceived as more urgent than regulatory and professional pressures. The main barrier was limited technical capacity rather than a lack of commitment to trust. The study proposes an Adaptive Digitalization Model with technical, organizational, and cultural pillars. The model is an initial framework that requires further testing. System-based trust can strengthen, rather than replace, personal trust.