Globally, more and more students with disabilities are choosing to continue on to post-secondary education following high school. Nevertheless, in comparison to their non-disabled peers, young people with disabilities are persistently underrepresented in this area. As with students without disabilities, a post-secondary diploma or degree will enhance opportunities for employment, both in terms of options and income. Bridging the gap between high school and post-secondary education can be daunting for most students, but with the added complexities associated with disabilities, the challenges will be intensified. Hence, a supportive and efficacious transition between secondary and post-secondary settings is not only helpful, but essential. For post-secondary education to be inclusive, it must be accessible. To be accessible, the transition must support the student by taking into account their strengths, challenges, interests, and goals, while considering the post-secondary environment. Successful transition plans must be student-centered, collaborative, begin early, and include measured and specific steps that are individually designed to help individual students bridge the gap. Key elements and considerations include: (a) assessing the environment and the fit; (b) developing the student’s self-advocacy skills; (c) tailoring accommodations based on the academic, social, and independent living skills of the student; and (d) supporting the student emotionally and mentally through the transition and beyond. Additional considerations include the use of assistive technology, mentoring programs, and familiarizing the student with the environment in advance of the change. Although often considered the panacea for the many academic and organizational challenges faced by students with disabilities, assistive technology is most beneficial if introduced early; this allows the student to experiment, select, and become familiar with it before leaving high school. Mentorship programs and supports, both formal and informal, should be given careful consideration as effective means of facilitating the transition. In addition to the academic and social challenges, the disruption of routines and the unfamiliar aspects of the post-secondary environment can be particularly daunting for students with disabilities. To negotiate and mitigate these aspects it might be beneficial to create opportunities for the student to become familiar with the post-secondary institution before going there. By easing and supporting the transition of students with disabilities in these and other ways, some of the barriers they face are ameliorated. Affording equal opportunity for students with disabilities to progress to post-secondary education and the subsequent workforce is not only just, it is a moral obligation and essential to an inclusive society.