The article is devoted to the examination of tax compliance as a system for preventing violations of tax legislation, on the one hand, assessing and managing tax risks, on the other hand. This approach to tax compliance allows for the examination of both: approaches, aimed at identifying violations of tax legislation, to the assessment of tax authorities' tax risks; and taxpayers whose goal is to optimize tax by lawful means. Tax compliance is analyzed as a system, simultaneously, of preventive and incentive measures of administrative enforcement as well. The analysis of the system of such measures is constructed having regard to both their purposes and the grounds for their application, the method by which they secure legal order, and the content of the measures in question. This has allowed the author to identify shortcomings in the legal regulation and in the practice of applying the measures under consideration of administrative enforcement for violations of tax legislation, as well as to devise and to propose in the article methods for resolving these problems. In the article, a conclusion is reached concerning improper legal and organizational guarantees of the implementation of the legal status of a taxpayer, a tax agent or a credit institution owing to the absence in tax legislation of a defined and closed (i.e. exhaustive) list of tax risks and criteria for assessing them. Such a conclusion is made based on systemic legal research of the mechanism of the legal regulation of tax control, specific aspects of organizing it, and the structure and legal status of tax control in Russia. Preventive measures of tax compliance are examined as part of a system of measures of administrative enforcement together with preclusive, provisional, punitive and restorative administrative enforcement measures are applied for the violation of tax legislation. At the same time, advantageously for the improvement of tax compliance, the prospects are assessed for a transition from vertical to horizontal tax relationships, i.e. wide implementation of tax monitoring as a method of tax control and a gradual withdrawal from tax audits to the extent that the effectiveness increases of a risk-oriented approach in tax control. However, all this is possible only if the concept of lawfulness is unconditionally embedded in the mechanism of legal regulation of tax control, such concept presupposing that all constitutional principles of taxes and levies will be implemented in legal regulation and law enforcement practice.