This paper proposes a strategic behavior categorization between the contractor and the provider in information technology (IT) outsourcing. We identified four behaviors (or attitudes) focusing specifically on the contractors’ attitudes: (a) conservative, (b) collaborative, (c) opportunistic, and (d) transformational. Theoretical concepts from IT Outsourcing, Relational Governance, and Knowledge Transfer were used to derive the study hypotheses. A questionnaire was developed to collect the information to test the hypotheses. An empirical analysis of a sample of 247 Brazilian companies was used, supporting the grouping of the companies as follows: 38.49% of them had the conservative attitude; 29.14% of them had the collaborative attitude; 14.97% of them had the opportunistic attitude; and 17.40% of them had the transformational attitude. We found that the relational attitudes should be adjusted to the individual contractors’ conditions, specific characteristics, and sectors. Our results also emphasize that the type of outsourced activity (traditional or customized) enables the managers to identify the need to balance the participation in relational governance. This study brings innovations to the understanding of the importance of the relationship between the contractor and the supplier, supporting, for example, the prioritization of new relational profiles according to the level of the IT service that was contracted, whether it is traditional or customized.