Outsourcing of external assignments and new autonomous collaborations within the Public Administration (P.A.) represent crucial topics in human resource management and the organization of public services within the Italian legal system. This study examines the legislative and jurisprudential evolution in this area, focusing on the Autonomous Work Jobs Act (Law 81/2017) and recent case law that has redefined the boundaries between subordinate and autonomous work within the Italian legal framework. The distinction between a work contract and subordinate work is explored, with particular attention to the essential characteristics of autonomous work, such as the absence of subordination constraints and organizational autonomy. Furthermore, the impact of the Jobs Act on human resource management within the P.A. is analyzed, emphasizing its relevance to Italian operators and those working within the Italian legal system.