The main research objective of the chapter is to provide an analysis of the technological quality evaluation models and make a proposal for a method suitable for the multiple criteria evaluation (decision making) and optimization of the components of e-learning systems (i.e. learning software), including Learning Objects, Learning Object Repositories, and Virtual Learning Environments. Both the learning software ‘internal quality’ and ‘quality in use’ technological evaluation criteria are analyzed in the chapter and are incorporated into comprehensive quality evaluation models. The learning software quality evaluation criteria are further investigated in terms of their optimal parameters, and an additive utility function based on experts’ judgements, including multicriteria evaluation, numerical ratings, and weights, is applied to optimize the learning software according to particular learners’ needs.