The paper analyzes jurisprudence of the courts of general jurisdiction with regard to disputes claiming recovery of dismissal allowances stipulated by an employment termination agreement. The author identifies errors in the field of application of employment law rules regulating guarantees and analizes errors committed by courts due to improper understanding of the legal nature of dismissal allowances. The author substantiates arguments and criteria that can be used to determine whether dismissal allowances are adequate and proportionate, examines the problems associated with the application of the principle of protection against discrimination in the area of employment and the general legal principle of inadmissibility of abuse of the right in employment relationships. According to the author, the practice of courts’ erroneous interpretation of the norms of the Labor Code of the Russian Federation governing the issues of dismissal allowances under the employment contract encourages us to develop understandable and detailed criteria using which the courts and the parties to the employment dispute will be able to rely on in dismissal allowances’ claims. Such criteria can be developed in the form of a system of review questions, answering to which the court and the parties would be able to reach a balanced and reasoned decision.