This paper discusses strategic flexibility and its impacts on the effectiveness of management of the IT outsourcing process. This is done by verifying how the strategic flexibility itself, the complexity of the environment, the flexibility of contracts and agreements and the types of IT outsourcing schemes influence the success of the IT outsourcing process, in an attempt to corroborate previous international studies, increasing their scope to the Brazilian context. In order to accomplish the proposed objective, a survey was carried out with industrial and service organizations in the state of Paraná, in the South of Brazil, which outsource their IT. In analyzing the data, factor analysis and multiple regression techniques were used, which helped confirming the influence of robustness, one of the dimensions of flexibility, on the effectiveness of outsourcing, providing an easier access to technology while improving control on the expenses. Increased access to technology was also perceived, in a more noticeable way, in the cases where the type of hiring was Business Process Outsourcing (BPO).