In a period where digital transformation has become a buzzword in every industry, the higher education sector can also be further improved using digital transformation. This study explores the limitations faced when supervising and evaluating the interns manually and develops an information systems-based solution to overcome such identified limitations. The Department of Information Technology, Faculty of Management Studies and Commerce, University of Sri Jayewardenepura in Sri Lanka was selected as the case by adopting a case study approach in qualitative research. Data was collected by interviewing the stakeholders of the process and observing the manual documents to determine the limitations of the manual process. Web-based technologies such as HTML and PHP were used to develop the system. Further rounds of interviews were held with the same stakeholders to validate the ISES. Shortcomings in the manual process including the tediousness of manual document keeping, the burden of interns in frequently visiting the university, absence of a centralized communication platform for all stakeholders in the process were revealed as themes from the thematic analysis. A web-based information system termed ISES was developed and validated as the outcome of this research to streamline the process of internship supervision by eliminating the above limitations. Novel findings were added to theoretical areas of how internship supervision could be improved by digital transformation while the ISES system developed offers a workable alternative for any university that allows internships as a requirement for degree programs to improve efficiency and effectiveness.