The manual nature of requesting documents in paper form and over-the-counter payments has continued to exist in many higher education institutions, thus creating long lines, misplaced forms, delays in processing, and exposure to document tampering. To counter these issues, this study designed and developed NU DROP, a secure, web-based system that uniquely integrates document requests with online payment processing in a single platform tailored for Higher Education Institutions (HEI). The system allows for online document requests, status tracking in real time, and multi-channel payments (with online facilities, such as GCash and PayMaya, and over the counter via SM Bills). The development process followed the Scrum methodology and took into consideration interviews, field observation, and document analysis. Key contributions include: 1) an end-to-end process unifying the registrar-accounting-user workflows; 2) QR-based verification to detect tampering of issued PDFs using server-validated cryptographic hashes; 3) inclusive payment options catering to both e-wallet and cash-based users; and 4) role-based dashboards with audit logging for transparency and accountability. Early stakeholder walkthroughs show evidence of better turnaround time visibility, less manual follow-up, and more consistent recordkeeping.