Despite rapid growth in online enrollment within higher education, persistence and completion rates remain lower for online courses than face-to-face courses. This discrepancy between the two modalities indicates a need to better understand students’ self-regulated learning (SRL) within online learning environments. Students with higher SRL skills demonstrate higher academic achievement than those who do not, and so it is critical to investigate the topic of SRL because it is so closely tied with achievement online. This study used a sequential, explanatory mixed methods approach to better understand the experience and actions of undergraduate students in an asynchronous online course who possess varying levels of self-regulation. In the quantitative phase, participants completed the Motivated Strategies for Learning Questionnaire which gave a self-reported snapshot into students’ motivation, self-regulating skills, and learning strategies. Trace log data from the learning management system (LMS) was additionally collected during four weeks of the semester. During an interim phase, three focal participants were selected and a semi-structured interview protocol was developed for the qualitative phase. The qualitative phase consisted of data collected through interviews with each of the focal participants, and observations of the three participants throughout the semester. Results suggest that while students appreciate the flexibility of an online course, flexibility can also lead to challenges. The flexible nature of a course appeared most challenging during online group work, when taking an online class for the first time, or when time management was poor. It was also found that students with higher levels of SRL strategies tend to dedicate specific time and places to work on coursework, and demonstrated a propensity to log in to the course LMS earlier and more frequently during each course week. Conversely, it was found that a student with lower SRL abilities did not dedicate a specific time or place to studying for the course, and tended to miss group discussion deadlines. Finally, it was found that an online instructors’ presence, frequent communication, use of video posts and discussions, and outlining weekly expectations were helpful teaching strategies which encouraged students to maintain motivation and SRL within the course.