Legitimacy gaps are the results of flaws and inconsistencies of asymmetric information and imperfect financial markets. The objective of this paper is to explore the role of tax advisors and the challenges that they are facing on information obligation, within the framework of legitimacy and stakeholder theories, combined with current research concerning voluntary corporate social responsibility and sustainability disclosures. After introducing briefly the role of tax advisors related to information obligation, the paper discusses legitimacy theory and stakeholder theory along with different views on CSR strategies on tax used by managers to solve issues that create legitimacy gaps and also techniques to either gain, maintain or repair legitimacy. It explores the basics of stakeholder theory as a framework for CSR strategies on tax development and its practical uses. The final discussion is focusing on the role of tax advisors in disclosing information since taxation and sustainability considered together and appropriately combined are in the interest of all.