Islamic boarding schools require coordinated digital support for student administration, payment processing, institutional communication, and basic financial reporting. At Al-Insap Islamic Boarding School, paper records and disconnected files fragmented student, guardian, payment, and transaction data. This study aimed to develop and functionally evaluate a role-based web platform that links guardian-submitted payment evidence to student identities, administrator verification decisions, corresponding financial transactions, payment histories, and period-based reports within a single relational workflow. The application was developed using Laravel, MySQL, Unified Modeling Language, and the Waterfall Software Development Life Cycle. Requirements were identified through observation, document analysis, and interviews with [N] participants comprising [N] boarding-school leaders, [N] administrative officers, [N] financial officers, and [N] student guardians. The system provides administrator functions for student-data management, income and expenditure recording, information publication, payment verification, balance calculation, and period-based reporting, while guardians can upload evidence, monitor verification status, and review payment histories. Functional evaluation used [N] executable black-box test cases grouped into nine categories and applied [real/anonymized/simulated] institutional records. All executed cases produced outputs consistent with the predefined requirements. These results support functional conformity and workflow-level traceability only within the tested scenarios; they do not demonstrate improvements in efficiency, accuracy, transparency, usability, security, satisfaction, or organizational accountability. The platform should therefore be understood as an integrated administrative and payment-tracking system, not a complete accounting or enterprise-management system with ledgers, reconciliation, budgeting, payroll, procurement, standardized financial statements, or formal auditing capabilities.