The principle of exhaustion is a fundamental legal doctrine that limits the distribution right of the copyright holder and aims to establish a fair balance between the protection of intellectual property and the free movement of goods. Traditionally designed for tangible copies (such as books, CDs, etc.), whether this principle also applies to digital content downloaded or accessed via the internet has become one of the most significant debates in modern copyright law. This article analyzes the boundaries of the exhaustion principle in the digital environment, particularly with regard to software and other digital works (e-books), by comparing the case law of the Court of Justice of the European Union (CJEU) with the jurisprudence of the Turkish Court of Cassation.