Graduate students hold several roles and responsibilities (i.e., learner, employee, teaching assistant, researcher, caregiver, etc.). Due to COVID-19, and the abrupt transition to virtual workplaces and learning environments during the spring 2020 semester, many graduate students encountered complex experiences and the blending of roles and responsibilities. This qualitative study included interviews with 22 graduate students about their experiences during the COVID-19 online transition at a land grant university. The four emergent themes included: (a) graduate students’ complexity of roles and experiences, (b) challenges and barriers experienced, (c) support structures available to graduate students, and (d) lessons learned and implications for the future. Recommendations for practice included creating opportunities for peer-connections and collaboration within virtual learning and work environments and professional development for course instructors in emergency remote teaching (ERT) and virtual settings. Recommendations for research included an investigation of best practices of online written interview methods, longitudinal study of graduate students as they move beyond graduate school to determine how ERT has affected their new roles, and further examination of graduate students’ needs and preparedness for delivering and receiving ERT