The chapter focuses on financial penalties and how technological tools can improve the enforcement of legal obligations by threatening financial penalties. These penalties impose a penalty on the debtor for failing to fulfill a court obligation or violating a court order. The penalty may be payable in small hourly, daily or monthly amounts until the obligation (related to the penalty) has been complied with or the violation has ended. A technological solution may be useful to improve the enforcement of financial penalties rather than other types of penalties, damages and legal interest. Criminal threats have clear and obvious effectiveness, but are still rarely used in some legal systems. This study anticipates how a technological solution can reduce a debtor’s resistance to payment, thereby improving judicial outcomes. Promotion and practical implementation of a technological solution can increase the effectiveness of the system, reduce payment resistance on the debtor’s side, and thus enable better results in the judicial area.