Although there is a need for gender-specific health care, especially within the context of vocational rehabilitation for youth with disabilities, clinicians, trainees, and community service providers commonly report lacking training in gender-sensitive approaches. Therefore, an educational tool designed for clinicians working with youth, that addresses how to approach such issues, could help clinicians to augment the care they provide. The objective of our study was to conduct a pilot evaluation of an educational simulation for health care and service providers focusing on gender-sensitive approaches within the context of supporting youth with disabilities in vocational rehabilitation. We conducted a survey from May to September 2021 to assess the relevance of the simulation content, preliminary perceived impact on gender-sensitive knowledge and confidence, and open-ended feedback of a web-based gender-sensitive educational simulation. A total of 12 health care providers from a variety of professions who had experience working with youth in the context of vocational rehabilitation participated in the survey (11 women and 1 man). Most participants reported that the content of the simulation was relevant and comprehensive. The majority of participants reported that the simulation helped to increase their perceived knowledge or understanding of the topic, changed their perceived understanding of their intervention or approach, and informed their perceived confidence. Our qualitative findings from the open-ended questions highlighted three main themes: (1) relevance of the simulation content, (2) perceived impact for clinical practice (ie, gender-sensitive language and communication and building rapport with patients), and (3) perceived impact on organizational processes (ie, practices, policy, and privacy). Our educational simulation shows preliminary potential as an educational tool for service providers working with youth who have a disability within the context of vocational rehabilitation. Further research is needed to assess the impact of the tool with larger samples.