A primary purpose of senior management is to make decisions around capital allocation that will improve the performance of the corporation. Portfolio analysis tools are designed to aid senior management in the development and analysis of portfolio strategies, by giving them the capability to assess the impact on the corporation of various investment decisions. To date most of the commercial portfolio optimization packages have been relatively inflexible and are often not able to answer the key questions asked by senior management. In this paper we will present new techniques that increase the flexibility of optimization tools and deepen the types of portfolio analysis that can be carried out. A new optimization engine, which contains state-of-the-art optimization functionality, allows users to simultaneously address financial return goals, catastrophic loss avoidance, and performance probability. These innovations enable users to confidently design effective plans for achieving financial goals, by employing accurate analysis based on real data. Traditional analysis and prediction methods are based on mean variance analysis, which is known to be faulty. The new techniques take a more sophisticated and strategic direction. State-of-the-art technology integrates optimization and simulation techniques into a global system that guides a series of evaluations to reveal truly optimal investment scenarios. Specifically, the new optimization techniques use an evolutionary approach called scatter search, reinforced by the adaptive memory strategies of tabu search. The software integrates state-of-the-art metaheuristic procedures, including Tabu Search, Neural Networks, and Scatter Search, into a single composite method. We will give some examples that highlight the importance and flexibility of the techniques applied to E&P portfolios.