The aim of the paper was to identify areas of possible abuse of social security support in the Czech Republic, with a specific focus on the Ústí nad Labem Region and the Litoměřice district, and to estimate the volume of social security support drawn in conflict with the legal regulations of the Czech Republic. In the Ústí nad Labem Region, spending on social security increased by 34.9% in the years 2016–2020. Upon a detailed focus on the Litoměřice district in the monitored period of 2018–2020, there were 69 fraud cases in the Litoměřice district within the scope of the social security system and illness benefit. Over 60% of this fraud and loss was deferred. The biggest shortcoming of the Czech Republic’s social system is the fact that individual institutions have little or no chance of finding out whether applicants are entering truthful information in the forms. A change of legal regulations and mandatory checks on applicants is the path towards reducing the amount of fraud and loss in social security and illness benefit.