This volume constitutes the refereed proceedings of the 5th International Workshop, HELMeTO 2023, held in Foggia, Italy, during September 13–15, 2023. The 52 full papers were carefully reviewed and selected from 107 submission. They are categorized in the following sections: Online pedagogy and learning methodologies and Learning technologies data analytics and educational big data mining and their applications, Smart Systems for Context-aware Education, Emotions and Art in Higher Distance Education and Performing art based methodology to improve online learning experiences, E learning for providing augmented mathematics education at University level, SuperCyberKids the importance of promoting Cybersecurity Education among teacher education students, Effects of High performance Artificial Intelligence systems and Immersive Technologies in Education, The Future of Learning Exploring the Intersection of Posthumanism E Health Technologies and Artificial Intelligence in Education Innovations, Technology based learning interventions in higher education for combating inequalities and increasing the psychological well being of youngsters, Innovative Inclusive University, Beyond borders: exploring immersive environments and new didactic approaches in higher education, Learning Technologies and Faculty Development in the digital framework.