This study is based on a sample of the thirty Chilean companies with the highest stock presence and which demonstrate opacity problems in their tax sustainability related to the GRI 207 standard available since 2019 (which emphasizes the disclosure of tax strategies to stakeholders, especially as regards any links with their small and medium-sized enterprises (SMEs)). The study also explores the literature related to tax transparency and its evolution in Latin America. Significantly different performances were found among the tax sustainability reports. The reasons for these differences are related to the fact that some demand simple declarations of principles, while others require both reporting of evidence in front of the interest groups and revealing of the tax strategy. As a result, taxpayers seem to use their corporate social responsibility activities more to moderate reputation risk than to aim at tax transparency. At the same time, the findings reveal that the actions toward tax transparency which have defined the tributary administrations of Latin American countries since the 2018 Punta del Este Global Forum do not consider the possibility of public disclosure. In this sense, the evidence highlights the need for Latin American policymakers to introduce, at the normative level, integrated tax transparency cooperation mechanisms between state administrations and regulated companies.