Successful delivery of transition services for students with disabilities remains a significant challenge in the developed and developing countries like Botswana as students continue to experience poor post-school outcomes. This study examined teachers' perceptions about barriers concerning the effective implementation of transition practices and principles in Botswana senior secondary schools. The researchers adopted a quantitative research approach using paper surveys to collect data from 258 participants. Teachers reported several challenges in the transition process and showed significant differences on transition barriers by teacher position and school region. Challenges noted among others included inadequate training of teachers and shortage of resources to support transition. Recommendations for practice include the formulation of a transition legal framework and provision of clear guidelines in the delivery of transition services.