The high school classroom setting is transitioning to meet the needs of the 21st century learner. Advancements in technology, such as the Internet and software platforms for web-based learning, have led to an increase in online learning over the last decade. The number of adolescents taking online courses has also increased due to these technological advancements and requirements from state departments of education for students to have an online learning experience in order to graduate from high school. This multi-site case study examined students' experiences and factors that influenced their satisfaction in their online courses at four high schools. The ultimate goal was to determine which specific factors led to satisfaction or dissatisfaction for students in these courses in order to help educators improve the online learning experience for their students. The results of the study indicated that the majority of the high school students were satisfied with the convenience and opportunities that the online learning environment provided for them. Communication and feedback were found to be vital components in determining whether or not the students had a positive experience in their courses. The data from this study can be used to provide insight for educators into the contributing factors that lead to satisfaction and dissatisfaction in the online learning environment and assist them in making the overall online learning experience positive for students.