(1) Background: During the two-year-long siege from the COVID-19 pandemic, a significant proportion of doctor visits transitioned from in-person to virtual. Scare evidence is available to assess the quality of patient-provider communication via the platform of telemedicine, especially for PrEP care within primary care settings. (2) Methods: Participants included 18 primary care providers and 29 PrEP-eligible women. Through content analysis and thematic analysis, facilitators and barriers embedded at different levels of telemedicine were identified and assessed. (3) Results: Women and providers reported pros and cons regarding their telemedicine experiences during the initial wave of COVID-19. Both groups of participants agreed that telemedicine visits were more convenient, efficient, and comfortable than in-person visits. However, without face-to-face interactions, some women felt less empathy, caring, and connected with their providers during virtual visits. Health providers expressed concerns with telemedicine, including patients’ privacy, lack of intimacy between patients and providers, and delayed lab work. (4) Conclusions: Our data indicate multi-level factors may affect telemedicine experience among PrEP-eligible women and health providers. Participants expressed concerns that may further entrench these long-existing health disparities in healthcare. Proactive efforts from policymakers, health professionals, researchers, and stakeholders are urgently required to tackle identified barriers and to pave the way for the new infrastructure that ensures health equity in society.