Long-acting injectable cabotegravir (CAB-LA) is in advanced stages of clinical trials. Under the standard protocol, CAB-LA is injected into the gluteal muscle by a healthcare provider every eight weeks. To explore transgender women’s barriers and facilitators to tailored delivery strategies—including self-injection and injection in “drop-in” centers—we completed in-depth interviews with N = 15 transgender women in New York City. Participants endorsed the alternative delivery methods and the corresponding features we proposed, and expressed likes and dislikes about each. These fell into the following categories: competence (e.g., the person delivering CAB-LA must have skills to do so), convenience (e.g., CAB-LA must be easy to obtain), and privacy or fear of judgement (e.g., participants did not want to feel judged for using CAB-LA by providers or other service consumers). Findings suggest the need to offer CAB-LA to transgender women through multiple delivery protocols.