It is now common knowledge, the regeneration of previously developed sites in urban areas can have positive impacts on the environment, the economy and the society as they constitute opportunities for the densification of the existing built fabric. In the context of the post-industrial European city, the urban wastelands offer thus an important potential of buildable surfaces and a chance to revitalize some portions of cities and metropolitan areas. Initiatives of this type are now strongly fostered by land use policies. However, it must be noted that in most cases references made to the concept of sustainable development are still often partial and superficial. Its integration requires a proactive and holistic approach, integrated in a participative way into the project dynamic, and a continuous assessment of the many dimensions of sustainability in regard with the specificity of these sites. The strategic integration of operational assessment into urban wastelands transformation projects is addressing specifically with these targets. Preliminary research projects have allowed to identify a first set of criteria and indicators based on specific characteristics of wasteland regeneration projects and to achieve a first test application on a concrete project. On the basis of that works, this paper shows the transposition of this set into a digital monitoring tool, entitled SIPRIUS, in order to create an operational assessment methodology that concretely facilitates the transformation of urban wastelands into sustainable neighborhoods.