This chapter explores the evolving role of metadata and paradata in the digitisation of cultural heritage and introduces the Memory Twin concept as a holistic framework that integrates both tangible and intangible dimensions of heritage. Drawing on historical milestones, technological advances, and European policy initiatives, it argues for a paradigm shift from data-centric to memory-enriched digitisation. The chapter presents insights from Heritage Malta’s digitisation initiatives, highlighting challenges related to standardisation, context loss, and ethical issues in emerging technologies like AI. It emphasizes the need for certified frameworks for metadata and paradata to ensure transparency, reproducibility, and long-term preservation. The Memory Twin approach captures not only the form but also the meaning, memory, and cultural narratives embedded in heritage assets. By incorporating participatory practices and interdisciplinary governance, it advocates for a more inclusive, context-sensitive, and ethically responsible future in heritage digitization.