This paper explores legal nature and practical implementation of plea agreements in the United States and Ukraine, with a particular focus on their use in cases involving economic crimes. It highlights the profound integration of procedural and substantive criminal law in the U.S. system and contrasts it with Ukraine’s fast evolving approach. The study emphasizes the dual purpose of plea agreements in American legal practice: facilitating efficient convictions and uncovering latent offenses in exchange for sentencing leniency. In Ukraine, the institutionalization of plea bargaining began only after the 2012 criminal procedure reform and remains underdeveloped. The analysis identifies challenges in determining sentencing parameters under plea agreements in Ukraine and critiques the overly punitive stance enshrined in Article 389–1 of the Criminal Code of Ukraine, which criminalizes non-compliance with plea or reconciliation agreements. The authors advocate for the repeal of this provision, arguing that returning to standard trial proceedings is a sufficient legal response to such breaches. Drawing on comparative insights, the paper calls for a balanced and restorative approach to the enforcement of plea agreements that respects due process while maintaining prosecutorial efficiency. It concludes with a notion that excessive criminalization seriously undermines the goals of modern criminal justice and thus should be reconsidered.