The use of learning media is currently growing rapidly. Today, many studies use computers as adaptive learning media for students; one example is the hypermedia learning environment (HLE). HLE media was developed to assist students in learning, such as the current situation of the Corona Virus Disease 2019 (COVID-19) pandemic which requires all learning activities to be carried out online. One of those affected fields is the education field, where all learning activities are transferred online, so HLE web-based learning can help students to keep learning from home. HLE is currently being developed to improve students’ abilities in the self-regulated learning (SRL) process. In SRL, there is an important component in it, namely self-monitoring. However, in its development, the developed HLE is not based on self-monitoring. In this study, an adaptive HLE was developed based on students’ self-monitoring abilities. In its development, the HLE system used the agile development method, namely Scrum. The initial data collection for student classification was the self-regulatory inventory (SRI). SRI was used as an instrument to measure students’ self-monitoring ability. The data were then processed to classify students into three classes, namely high, medium, and low. Subsequently, the results of the classification of student abilities were used to develop learning aids in HLE. The development assistance provided was in the form of text and videos that were adjusted to the level of student self-monitoring. From the results of the development, it was found that all HLE functions could run well. The system was tested on twelve students to determine the level of usability by using the system usability scale (SUS). The results were classified as good category, with a score of 72.92. Further research can apply this method to students and measure the effectiveness of the system that has been developed.