In Italy, N-NDOs and NDOs coexist and both are supported by indirect rationales. Under a national rule and regional regulations, the dedication of land for public use and monetary contributions for basic infrastructure are mandatory in municipal legally binding plans since the end of the 1960s. They have effectively produced a betterment in the urban welfare, albeit unevenly distributed in the country. Due to public budgetary cuts, municipalities have progressively adopted agreements to obtain additional private contributions in the major redevelopment areas. On- and off-site improvements in green areas and social housing are the main scope of negotiations. Although these additional obligations are often regulated in advance in urban planning tools, conflicts among local authorities and private developers may arise because of their amount. In 2014, a national act introduced an extra contribution for value recapture based on direct rationales. Two Milano case studies present the integration of N-NDOs and NDOs, and this recent extra contribution.