Local power distribution companies are not self-sufficient in electricity to serve their customers, and require importing additional energy supply from the interconnected bulk power systems. In Brazil, they annually carry out the contracting process for the amount of transmission system usage (ATSU) for the next four years. This process is a real example of a task that involves decisions under uncertainty with a high impact on the productivity of the distributions companies and on the electricity sector in general. The task becomes even more complex in face of the increasing variability associated with the generation of renewable energy and the changing profile of the consumer. The ATSU is a random variable, and being able to understand its variability is crucial for better decision making. Probabilistic power flow is a technique that maps the uncertainties of nodal injections and network configuration in the transmission equipment and, consequently, in the imported power at each connection point with the bulk power system. In this thesis, the main objective is to develop methodologies based on probabilistic power flow via Monte Carlo simulation, together with cross entropy techniques, to assess the risks involved in the optimal contracting of the ATSU. The proposed approaches allow the inclusion of commercial software to deal with the power flow algorithm, which is relevant for large practical systems. Thus, a realistic computational tool that serves the engineers of electric distribution companies is presented. Results with academic and real systems show that the proposals fulfill the objectives set, with the benefits of reducing the total costs in the optimization process of contracts and computational times involved in the risk assessments.