One of the relevant strategies to limit the sprawl of post-industrial European cities is the regeneration of urban brownfields. This type of projects concentrates new development within already urbanized areas and contributes to their revitalization. Despite this, projects developed on urban brownfields are not automatically sustainable. It is explained by their inherent complex nature, due to the specificities of the site, the project process and the sustainability concept itself. Focusing on these challenges, SIPRIUS+ is an operational monitoring tool using an interdisciplinary approach. It supports a search for global quality, tailored to urban brownfields regeneration projects and integrated into the project dynamics. This new generation tool is a hybrid between a sustainability indicator system adapted to issues raised by brownfield regeneration and an user-friendly, web-based monitoring software. SIPRIUS+ assists practitioners in their decision-making: it facilitates the integration, assessment, and follow-up of sustainability indicators during the transformation of urban brownfields into new environmentally friendly and socially inclusive neighborhoods, respectful of future generations. This paper gives a description of the different steps of the tool’s design and an overview of its functionalities. Then, the main features of SIPRIUS+ are presented through a test application on a case study located in Yverdon-les-Bains (Switzerland).