In this three-year, mixed methods case study, the benefits and challenges of online learning for at-risk high school students were examined. A key finding was that at-risk students identify the benefits and challenges of online learning to be the same. While students appreciate the opportunity to work ahead and study at their own pace, they see it as a challenge to be responsible for their own learning and manage their time. The authors of this paper argue that, with proper support structures in place, students who are at-risk for dropping out can overcome challenges and find success in an online learning environment.