Increased uncertainty and greater financial stakes in distribution system reliability has brought focus on more efficient and powerful tools to evaluate the risks within distribution system operation. It is quite common that countries or regions that have re-regulated its electricity market apply more heavy handed regulatory approaches for controlling its remaining monopoly, i.e. the grid operations. Applying quality dependent revenue or price caps is the most common way to introduce an environment that somewhat resembles competitive conditions. Traditional methods to evaluate distribution system reliability are usually rather simple and therefore have many advantages due; however, a more complex risk environment for the Distribution System Operators (DSOs) calls for better methods to analyze risks. This paper introduces a basic Monte Carlo Simulation method for distribution system analysis that can be used as an initial simulation method and input to a more powerful and comprehensive Monte Carlo model. Furthermore, the paper also introduces an idea of how to apply a variance reduction technique that resembles importance sampling on the presented Monte Carlo method.