The digitalization of tax administration and the mandatory implementation of electronic reporting frameworks—such as the myDATA platform in Greece—are fundamentally reshaping the tax compliance landscape and corporate audit procedures. This study investigates how the adoption of myDATA has influenced the nature and frequency of tax-related disclosures made by statutory auditors, focusing specifically on companies listed on the Athens Exchange (ATHEX). Employing content analysis on published Annual Independent Auditor's Reports, the paper examines whether the transition to digital books has altered tax-related Key Audit Matters (KAMs), modified audit opinions, or generated specific emphasis of matter paragraphs. By comparing audit disclosures between the pre- and post-myDATA implementation periods, the research evaluates whether enhanced digital transparency reduces traditional tax risks (e.g., VAT discrepancies, revenue recognition issues) or introduces new compliance challenges related to systemic data mapping and transmission discrepancies. The anticipated findings aim to provide empirical insights into the effectiveness of digital tax reporting tools from an external auditor's perspective, contributing to the academic literature on tax technology and auditing in capital markets.