This study describes the advantages and disadvantages of information technology outsourcing to Ukraine and Russia. The results assist technology managers who wish to make an informed decision on whether or not to outsource information technology projects to Russia/Ukraine, considering two important issues: (1) the political, economic, and social landscape, and the advantages and disadvantages of choosing to locate information technology projects in the region and (2) the Russian/Ukrainian information technology workers’ teamwork perceptions. By understanding the countries and the potential information technology workers within that country, organizations should be able to develop management policies to improve chances of success. While the results indicate that well-educated and teamwork-oriented Russian and Ukrainian information technology employees may increase the chances of information technology outsourcing success, the authors remain skeptical regarding the political, economic, legal, social, and business environments.