Debureaucratization initiatives are usually welcomed due to the anticipation of its benefits. Although such was the case of Simplex, its effectiveness is yet understudied and thus this scientific article aims to make a balance of the implementation of Simplex project. This balance covers both its effectiveness on the specific case of the Portuguese Social Security System as well as its levers and blockages in the ultimate goal of debureaucratize. The scarcity of information about Simplex impact encouraged this exploratory research as well as the methodological option that backed up a qualitative approach. To meet the study’s goals, this paper also incorporated theoretical elements of the literature review. We selected two Social Security stakeholders as our target groups – accountants and officials. With the former, we conducted individual semi-structured interviews, and with the second, we made focus groups. Findings suggest Simplex is much more than deadlines and cost decrease, and improving people’s lives. It is not just information and communication technologies (ICT), administrative simplification and legislative simplification, or as we called it, the triangle of drivers legislation, technology and procedures, but it is much more.