Purpose: Already at high-risk for adverse consequences associated with daily living, youth experiencing homelessness face additional barriers to health and well-being during the COVID-19 pandemic. The purpose of this study was to identify the self-reported experiences and healthcare needs of youth experiencing homelessness as services in the community began to shut down at the beginning of the pandemic. Method: From May through November 2020, qualitative data were obtained by telephone or Facebook messenger from 20 youth (M = 22.4, SD = 2.64 years) who had been enrolled in a longitudinal intervention study. Results: Content analysis of qualitative data yielded 5 categories and 1 overall theme. Categories were resource availability, financial instability, mental health, relationship conflict, and maladaptive coping. The overall theme was multiple losses. Youths lost jobs, means of financial support for self and family, access to social and healthcare services, meaningful and important relationships, and skills and controls over high-risk behaviors such as substance abuse. Conclusions: Having similar experiences such as social isolation as those of high school students during the pandemic, the youths in this sample experienced multiple and simultaneous losses, needing time to grieve, and leaving them once more at high-risk for adverse outcomes.