The vending machine industry has evolved from conventional to connected machines. Vending machines are currently in wide use and typically involve a remote machine holding a plurality of products or items to be dispensed after receiving money from a purchaser. The industry has gone beyond just delivering snacks and is developing new and sophisticated retail solutions for both large and small companies. In this study, a qualitative inquiry was conducted in one of the branch universities of the largest public universities in Malaysia. A total of three vending machine entrepreneurs were qualitatively interviewed individually. Interviews were transcribed and analyzed to find a common theme. As a result, three challenges were identified: using a lot of paper, being time-consuming, and having no alert process. Contract renewal is significant and should not be taken for granted and it is a far-sighted move for a business manager to use the most efficient process from start to end. The respondent agreed that the current renewal process is redundant and time-consuming. Therefore, the researchers proposed to all the parties to reduce the hassle of renewing the contract. Based on this research, the authority department in public or private universities can develop an innovation in monitoring systems to improve the process. The results can provide suitable coping strategies for business owners to have the best practices for a contract renewal mechanism.