Background In 2020, many family members were thrust into the role of caregiving for a relative with COVID-19 with little preparation, training, or understanding of the disease and its symptoms. Objectives To explore the barriers to and facilitators of caregiving experienced by family caregivers of patients with COVID-19 who had been in intensive care in the pandemic’s earliest months. Methods In-depth qualitative interviews were conducted by web conference with 16 adults recovering at home after intubation for COVID-19 in an intensive care unit at a major academic medical center and their primary caregivers from March to August 2020 (N = 32). Thematic qualitative analysis was done using Watkins’ rigorous and accelerated data reduction technique with MAXQDA software. Results Seven themes emerged regarding factors that facilitated or posed barriers to care: other health conditions that increased complexity of care, interactions and experiences in the health care system, COVID-19’s proliferation into other areas of life, the psychological well-being of the patient-caregiver dyad, experience of support from the dyad’s network, the role of caregiving in the dyad, and contextual circumstances of the dyad. The themes often included both barriers and facilitators, depending on the experience of the dyad (eg, feeling encouraged vs fatigued by their support network). Conclusions Understanding how patients with COVID-19 and their caregivers experience illness management across the recovery journey can help clarify the COVID-19 care-giving process and identify intervention targets to improve overall health and well-being of the care dyad.