Background: In Kenya, adolescents spend much of their formative years in secondary boarding schools, which can provide a unique challenge for antiretroviral adherence support among adolescents living with HIV (ALHIV). It is important to understand the school experiences of ALHIV, their caregivers and school nurses to inform intervention models aimed at creating a supportive environment for ART adherence in Kenyan boarding schools. Methods: Between July 2022 and November 2022, we conducted (FGDs) among ALHIV attending boarding schools and caregivers of ALHIV, and (IDIs) with school nurses. Clinic records were used to identify ALHIV and caregivers. We categorized the boarding schools within Nairobi into national, county, and sub-county levels. Two schools were selected from each category; permission from the head teacher was obtained and school nurses invited to take part in virtual IDIs. All participants gave written informed consent. The interviews were audio-recorded, transcribed verbatim, and analyzed thematically. Results: We conducted two FGDs with 11 caregivers and two FGDs with 18 adolescents; we also conducted 7 IDIs with school nurses. All ALHIV reported having disclosed their HIV status to school nurses during opening, while caregivers sometimes disclosed to nurses as part of the school enrollment process. Both ALHIV and nurses reported minimal interaction with school nurses. Some ALHIV reported participating in support clubs established by peers or in partnership with school nurses. School nurse friendliness, understanding, fairness, and confidentiality were features associated with ALHIV willingness to confide in them. Other ALHIV reported going to the nurse's office to take medication but not desiring any additional interaction or support. Strategies ALHIV use to take drug includes: when other students were engaged in other activities, waking up early, stepping away from others, and stating their drugs are for different diseases. Caregivers were nervous about school-based adherence activities, fearing it could lead to inadvertent disclosure of the teen's HIV status and to stigmatization by fellow students. School nurses reported lacking specific training in HIV adherence for teens. Conclusion: ALHIV have devised strategies to navigate pill-taking. Establishment of a strong school nurse-adolescent rapport, and nurses' skills are key to improving school-based support for ALHIV. [ABSTRACT FROM AUTHOR]