The transition from individual and dependent learning style into collaborative and self-regulated learning is a challenge for new students in higher education.Self-monitoring process is one of the methods that can be used to answer the challenge.In addition,lecturers also need to monitor students' understanding about certain topics.A web-based selfmonitoring tool was developed using prototyping paradigm and user-centered design process.The features of the tool include create prompts,view the students' answers by the prompt or student's name,and give feedback to the students based on keywords appeared on their answers.Usability testing was conducted to measure how usable is the system.We then revised the system from the users' recommendations.