Nowadays, higher education worldwide is affected by the COVID-19 pandemic. It has affected students’ attendance in the universities and causes universities to close down in more than 190 countries. On the other hand, novice engineers studied only a few lectures related to highway engineering. Their lectures have included very little knowledge about asphalt pavement construction as highway engineering consists of many areas that are not studied in detail during their studying years subject to their traditional education. Due to all mentioned, a new drive to promote online learning paves the way to evaluate our future approach to curriculum development and delivery of educational materials for engineering courses. However, experts can offer solutions to these problems using their past experience. Hence, a system that allows experts to share their experience with other engineers after completing a project is needed. Nevertheless, the web-based expert system for maintaining flexible pavement problems in tropical regions (ESTAMPSYS) designed in this study is a novel concept. Prior to developing this system, the need for such a system was determined through literature review and validated through a questionnaire survey. Experts were interviewed, and a questionnaire survey was conducted to construct the knowledge base of the system. Knowledge was presented as rules and coded in software through PHP programming. Web pages that support the user interface were designed using a framework that consists of CSS, HTML, and J-Query. Furthermore, the system was tested by an array of users engaged in highway engineering, namely, experts, teaching experts, novice engineers, and students. The mean values of the overall system evaluation performed by 20 users using a five-point Likert scale were 4, 4.5, 3.75, 4.25, 5, 4, and 3.5. Expert and user satisfaction prove the effectiveness of the proposed system.