As universities transitioned in-person classrooms to virtual classrooms, instructors faced challenges and changes in how they conduct their classes and teaching style trying to keep virtual classrooms as similar to in-person as much as possible through the use of group work in breakout sessions. Within these breakout sessions, students are expected to work together to complete an assignment. Through 669 surveys and 19 interviews, our paper outlines the successes and challenges of breakout sessions and teamwork in virtual learning environments faced by professors, graduate teaching assistants, and students. Our findings show the importance of pedagogical research for online environments, the student need for persistent instructions and check-ins to facilitate teamwork in breakout sessions, and strong justification for the use of breakout sessions in online courses. Based on our findings, we propose design recommendations to address the challenges highlighted within the classroom and software used by instructors and students. Our work contributes and extends previous CSCW and HCI research in online distributed teamwork and education.