This collection of conference papers presents the Proceedings of the 5th Crossing Boundaries Conference in Vocational Education and Training taking place from 25 to 26 May 2023 in Kaunas, Lithuania. The special focus of this conference is on the vocational education and training transformations for digital, sustainable and socially fair future. The proceedings of the 5th conference include 56 papers written by more 115 scholars according to the three thematic strands: systems and policy of VET and lifelong learning, educational institutions and institutional settings in the VET and skill formation, VET actors and stakeholders. The topics of conference papers are very diverse and provide insights on the VET development in the conditions of digitalization, changing roles of the VET providers, teachers and learners, sustainability of the VET provision, challenges of the VET provision in the developing economies, empowering effects of VET, changing roles and work of VET teaching staff and many other issues.