Purpose: Many youths with disabilities find it challenging to disclose their medical condition and request workplace accommodations. Our objective was to explore when and how young people with disabilities disclose their condition and request workplace accommodations.Methods: We conducted 17 in-depth interviews (11 females, six males) with youth with disabilities aged 15–34 (mean age 26). We analyzed our data using an interpretive, qualitative, and thematic approach.Results: Our results showed the timing of when youth disclosed their disability to their employer depended on disability type and severity, comfort level, type of job, and industry. Youth’s strategies and reasons for disclosure included advocating for their needs, being knowledgeable about workplace rights, and accommodation solutions. Facilitators for disclosure included job preparation, self-confidence, and self-advocacy skills, and having an inclusive work environment. Challenges to disability disclosure included the fear of stigma and discrimination, lack of employer’s knowledge about disability and accommodations, negative past experiences of disclosing, and not disclosing on your own terms.Conclusions: Our findings highlight that youth encounter several challenges and barriers to disclosing their condition and requesting workplace accommodations. The timing and process for disclosing is complex and further work is needed to help support youth with disclosing their condition.Implications for rehabilitationClinicians, educators, and employers should emphasize the importance of mentoring and leadership programs to give youth the confidence and self-advocacy skills needed to disclose and ask for accommodations in the workplace.Clinicians should advocate for the inclusion of youth with disabilities in the workforce and educate employers on the importance of doing so.Youth with disabilities need more opportunities for employment training and particularly how to disclose their disability and request workplace accommodations.