The complex and multi-level nature of legal regulation determines the complexity of law enforcement in resolving cases on disputes arising from targeted training agreements. In addition to the industry attribution of the contractual structure, there are a number of interconnected problems therewith, namely determination of the limitation period, jurisdiction of the dispute, legal assessment and application of liability measures (in particular, a fine paid to the educational organization). The author supports the point of view that targeted training agreements are similar with apprenticeship agreements. At the same time, the author points out that the new model of responsibility under the targeted training agreements is, on the one hand, a prerequisite for the differentiation of these contracts, but on the other, demonstrates some features of a public law nature that are unusual for both civil and labor law. These are expressed in establishing responsibility for violation of a contractual obligation to a third party, namely an educational organization. The author also highlights the uncertainty of the legal assessment of the deadline for paying a fine in connection with failure to fulfill an employment obligation and proposes to consider it a prerequisite for the right to claim in the substantive sense.