Young men who have sex with men (YMSM) are disproportionately affected by HIV in the United States. High-risk sexual behaviors are difficult to modify; thus, HIV pre-exposure prophylaxis (PrEP) with a daily pill is a promising prevention tool for this vulnerable population. We present a case of a young black MSM who was able to successfully access PrEP with the help of a community program but was not able to adhere to the regimen or engage in care. He ultimately acquired HIV infection. We review the existing literature and advocate for increased services and research to support youth's adherence to PrEP and engagement in HIV prevention programs, with a focus on YMSM of color.