The article provides a comparative analysis of some ineffective and valid rulings of the Plenum of the Supreme Court of the Russian Federation regarding application of labor law provisions. In particular, the author examines controversial issues arising in the enforcement practice concerning termination of an employment contract at the initiative of the employee and the employer. In the effective rulings of the Plenum of the Supreme Court of the Russian Federation, there are two de facto different approaches to the issue of the date of the employee's dismissal if an organization is liquidated. It appears that the date of the employee's dismissal must coincide with the date of an intermediate financial statement approval. Certain difficulties are caused by issues related to the failure of the employer to comply with the time limits set forth in the Labor Code of the Russian Federation regarding the procedure of warning an employee about impending discontinuation of an employment contract (a two-month period of dismissal in case of staff reduction and a three-day period in case of the employment contract expiration). The article examines inconsistent court practice regarding the procedure of recognizing absence of an employee from the workplace without a good reason for more than four consecutive hours as absenteeism, discusses advantages and disadvantages of Paragraphs 20 (discontinuation of employment at the initiative of an employee), 35 and 39 (order of employment discontinuation for culpable violations of labor duties) of Ruling № 2 of the Plenum of the Supreme Court of the RF of 17 March 2004, as well as matters relating to material liability of an employee for the damage caused to the employer while fulfilling labor duties. The problem amounts to the question whether it is legitimate in this case to claim damages from an employee under civil law. This issue was previously resolved by Ruling №8 of the Plenum of the Supreme Court of the USSR of 23 September 1987. The paper indicates that the new chapter of the RF LC requires an immediate clarification concerning peculiarities of regulation of the work of employees (staff) who are sent temporarily to other physical or legal entities under the secondment contract by their employers.