This article reports on the pilot work for a collaborative National Health and Medical Research Council project in Australia involving education and health professionals to improve the health and well-being of young people who have an intellectual disability. The pilot study was a qualitative exploration of teacher experiences using a health diary as part of the special education curriculum over a six-month period. The research questions were: (1) How did teachers include health-related matters in the curriculum before use of the Ask Health Diary?; and (2) How did teachers and students use the Ask Health Diary as a component of the school curriculum and what were the benefits? The Ask Health Diary was used to introduce students to the concept of self-advocacy in relation to their health needs and provide practical strategies for supporting students’ learning about self-advocacy in relation to their health. The reported data indicates that the Ask Health Diary was a popular resource for students and teachers and raised awareness of the importance of developing the communication skills and independent living abilities necessary for young people to advocate for their own health needs. The pilot study indicates that there is merit in including the diary in a health-based school curriculum for adolescents who have an intellectual disability.