Background/Objectives: The aim of the study is to analyze the patterns, trends and characteristics of concluding settlement agreements between the taxpayer and the tax authority in the Russian courts. Methods/Statistical Analysis: The authors used a set of philosophical, general and specific scientific methods of theoretical and empirical material cognition. In the present study, a dialectical materialist method was used to study the procedural and tax legal norms in the context of their interconnection, interdependence and divergence taking into account comprehensiveness and objectivity of the study. Findings: In the UK, the USA and Canada, most of the judicial tax disputes end by a conclusion of settlement agreements, which helps to significantly reduce social tension and the workload in the courts. The practice of the Russian courts is contradictory, which causes a legal uncertainty, negative impact on the overall tax climate in the Russian Federation. Creation of a single supreme judicial authority in Russia (the Supreme Court of Russia) requires the elimination of the existing legal uncertainty and ensuring a uniform approach to the solution of controversial issues. Previously, the problem of a settlement agreement conclusion was studied either in terms of the arbitration procedural legislation, or in terms of the tax one. Meanwhile, the court approval of the settlement agreement between the taxpayer and tax authority is a multifaceted problem. The legal system is a single organism, a complete improvement of which is possible only using an integrated approach. The authors analyze the position of the judicial and tax authorities, as well as their statistical data. Application/Improvements: The comparative legal study allows determining the main directions for the comprehensive improvement of legal norms to eliminate legal uncertainty, forming a comfortable tax environment and optimizing the judicial system.