While it’s essential for “intelligent enterprises” to deliver value added to their customers it’s getting increasingly important for them to consider new challenges in electronic payments. This is to meet the users’1 requirements to pay in a secure, efficient and “easy to use” way, both in e-commerce and m-commerce. In the end, secure and efficient2 electronic payment systems are one of the most crucial elements of transactions in e- and m-commerce. Currently, one can detect opacity3 for users because of the huge number of different payment systems and their different impact on the users’ individual requirements in different transaction situations posing them possible risks. Thus, assuring users of features such as convenience, low costs and privacy while conducting transactions may form the basis of competitive advantage for intelligent enterprises. This chapter presents an approach enabling users to evaluate possible risks related with electronic payment systems and hereby eliminating the above mentioned opacity. It highlights the definition of user requirements as a prerequisite for individual risk management. The solution introduced assists users in choosing a convenient payment system in the long term during individual portfolio-setup as well as in the short term while conducting payment transactions.