In this paper we attempt to break down the barrier of choosing a supportive technology for learning. We try to simplify the process by reducing it to a set of elementary steps. A perfect fit is difficult to achieve, in part due to the multitude of subjective interpretations. Having an in depth understanding in the different elements involved in choosing a appropriate technology, will make the decision process easier. We propose to evaluate both the technologies and courses on basis of a rating on characteristics. This forms the basis for the matching. The closer the match, the more likely the technology will be appropriate.