(1) The main purpose of this article is to analyse the relationship between risk factors and the benefits of Information Technology Outsourcing (ITO). For this purpose, a structural model was created to determine the dependency of the benefits on the importance of the risk factors associated with this service. (2) The research methodology included: a literature review, descriptive analysis, and empirical and formal methods. A survey questionnaire was used to collect data, and structural equation methodology was used to build and verify hypotheses. The structural model was tested on data from business practice - 200 large organizations, mostly enterprises, operating in Poland and using IT outsourcing. (3) The purpose was accomplished by determining the relationship between the IT outsourcing benefits and the risk factors' importance. The strongest relationship exists between supplier-related risk factors and technological benefits, while a slightly weaker relationship exists between economic risk and economic benefits and customer-related risk and organizational benefits. The weakest relationship exists between security risks and strategic benefits. (4) The article’s originality and value consist in establishing the existence of a relationship between risk factors and the benefits of IT outsourcing, and in identifying which groups of risks have the strongest impact on the benefits of ITO, which can be exploited by the service suppliers.