This study describes the advantages and disadvantages of IT outsourcing to Ukraine and Russia. Our results assist technology managers who wish to make an informed decision on whether or not to outsource IT projects to Russian/Ukraine, considering two important issues: 1) the political, economic, and social landscape, and the advantages and disadvantages of choosing to locate IT projects in the region; and 2) the Russian/Ukrainian IT worker’s potential and how teams may positively contribute to IT project success. While our results indicate that well-educated and teamwork-oriented Russian and Ukrainian information technology employees may increase the chances of IT outsourcing success, we remain skeptical regarding the political, economic, legal, social, and business environments.