The increasing digitization of information has led to unprecedented challenges in managing digital inheritance, post-mortem privacy as well as the fate of cultural heritage in the digital realm. This paper explores the legal, ethical, and technological dimensions of posthumous data management, focusing on the ambiguity of GDPR’s application to diseased individuals’ and the diverse domestic approaches within the European Union. Additionally, it examines how digital platforms shape the preservation or erasure of cultural heritage, raising concerns about accessibility, ownership, and historical continuity. The transformation of tangible cultural artifacts into digital assets further complicates inheritance laws, as emerging technologies, digital preservation methods and evolving memorial traditions continue to reshape both personal and societal legacies. The interplay between corporate interests, regulatory frameworks, and user rights introduces further complexities, necessitating a balanced approach to digital legacy governance. While no universal solution exists, an interdisciplinary approach involving law, technology, and ethics is essential to ensure that digital legacies — both personal and cultural — are preserved responsibly for future generations.