The key to enhancing electricity restructuring is to have an adequate competition in the generation sector of power industry. This concept requires a sufficient transmission capacity to support trading in electricity markets, while maintaining the system reliability. However, transmission expansion planning (TEP) for managing adequate transmission capacity is a major challenge which involves uncertainties and risks in restructured electricity environment. This study reviews TEP issues in a general perspective and addresses challenges in Turkey where the liberalization or the electric power industry is underway for establishing a competitive electricity market. A few strategies are proposed in this paper which are directed toward managing the risk in ensuring adequate transmission expansion in Turkey.