The transition from an urban brownfield to a sustainable neighbourhood is a complex operation. To help decision-makers reach sustainability objectives through measurement, follow-up, and communication about performance indicators, we introduce in this chapter a tailor-made operational monitoring tool. Such a tool should satisfy three general requirements: a search for overall quality, adequacy with the specificities of urban brownfield regeneration projects, and integration into the project dynamics. Accordingly, the multi-criteria evaluation system SIPRIUS and the quality management monitoring software OKpilot are hybridized to create SIPRIUS+. In the first section, we explain the functioning of the two existing methodologies and the adaptions we made to help meet the general requirements and to create the hybrid tool. Then, we present the resulting monitoring tool, SIPRIUS+, and its functionalities.