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Among the different quality attributes of software artifacts, security has lately gained a lot of interest. However, both qualitative and quantitative methodologies to assess security are still missing. This is possibly due to the lack of knowledge about which properties must be considered when it comes to evaluate security. The above-mentioned gap is even larger when one considers key software development phases such as architectural and detailed design. This position paper highlights the fundamental questions that need to be answered in order to bridge the gap and proposes an initial approach.