In this paper, we describe how the usability of software functionalities are promoted and evaluated during the design phase of a software project developing security-related functionalities in a middleware. The paper describes our work-in-progress in GEMOM project, challenges faced in the beginning of the project, and our plan to overcome those challenges with a clearly defined usability implementation plan. Categories and Subject Descriptors D.2.9 [Software Engineering]: Management – Software quality assurance (SQA)