Pre-exposure prophylaxis (PrEP) is a highly effective biobehavioral strategy for preventing HIV acquisition. Although PrEP uptake has increased steadily, discontinuation rates are high among members of key populations like gay and bisexual men (GBM). Understanding the challenges that arise for PrEP users is key to better PrEP implementation and sustained use over time. We report on barriers that arose for PrEP-using GBM, as well as facilitating factors that aided PrEP persistence, with the goal of informing PrEP implementation efforts. In 2015-2016, 103 PrEP-using GBM in NYC completed qualitative interviews about their engagement with PrEP, including their experiences navigating PrEP-related medical care. Interviews were transcribed verbatim, coded, and analyzed thematically. Over half of participants (53%) received their PrEP-related care from their primary care provider (PCP), one-third (33%) from a community-based health clinic, and 13% from multiple medical providers. Emergent themes regarding the barriers and facilitators to PrEP persistence fell into two categories: insurance- and medical appointment-related barriers and facilitators to continued PrEP use. The experiences of PrEP-using GBM can provide useful insights for providers, program developers, and policymakers aiming to improve the implementation of PrEP. To support PrEP persistence, reliable insurance coverage, cost-assistance, and easy appointment scheduling are key to maintenance. Removing insurance- and appointment-related barriers to persistence may prove essential for sustaining use among GBM.