This exploratory research addresses the state of student self-regulation (SR) in an online secondary school. Students are more likely to be successful, especially in online schools, when they are self-regulated. Understanding these students' current SR abilities can facilitate targeted interventions. Data for this study was gathered from a student survey and interviews of students, parents, and teachers from an online secondary school. Quantitative and qualitative analysis revealed that many students perceived their SR as being adequate to strong and that students were more aware of the help-seeking and time management dimensions of SR than of the other dimensions. This awareness aligned with the structure of the school that emphasized these two SR activities. Findings also indicated that poor mental health had a strong dampening effect on a student's SR abilities and that students' understanding of motivation was tied to their ability to overcome difficulties and to complete work. Finally, students' character traits seemed to both precede and support the development and use of SR dimensions. These findings suggest that targeted support for SR dimensions; an understanding of how mental health affects SR; the role of motivation; and an emphasis on character growth can support and promote SR growth.