Career planning plays a salient role in determining the individuals’ goal setting, work engagement, and outcomes. In school settings, helping students to establish good career planning would contribute not only to maximize their potential to learn and achieve based on their personal strengths, but also to suit their career development needs. However, to students with special educational needs (SEN), they are usually the group facing greater challenges in career planning and development compared to regular students. In the Hong Kong context, the present study took the initiativeto examine the aspirations, expectations, and challenges of post-secondary school transition among SEN students and their parents. A qualitative approach through a series of focus group interviews was adopted. Over 70 SEN students from both mainstream schools (n =38) and special schools (n =34) and 37 parents of SEN student participated in this study. The results were categorized into career aspirations, difficulties and challenges, expectations and recommendations of SEN students and their parents. The results draw educators’ attention of the found inadequacy of positive attitude to career planning and low confidence levels to achieve desirable post-school transition outcomes among SEN students. Implications are discussed in relation to SEN students’ needs of career planning training and career development.