E-learning markets have been expanding very rapidly. As a result, the involved senior managers are increasingly being confronted with the need to make significant investment decisions related to the e-learning business activities. Real options applications to risk management and investment evaluation of Information and Communication Technologies (ICT) have mainly focused on a single and a-priori known option. However, these options are not inherent in any ICT investment. Actually, they must be

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... arefully planned and intentionally embedded in the ICT investment in order to mitigate its risks and increase its return. Moreover, when an ICT investment involves multiple risks, by adopting different series of cascading options we may achieve risk mitigation and enhance investment performance. In this paper, we apply real options to the e-learning investments evaluation. Given the investment's requirements, assumptions and risks, the goal is to maximize the investment's value by identifying a good way to structure it using carefully chosen real options.