The participatory process activated by the research on shrinking small-town renaissance involved several stakeholders, experts, and local government representatives, particularly in Valtellina and Sicily, where planning workshops have taken place. This chapter collects and synthesizes interactions with a selection of them: voices from the territory but also updated scenarios and visions with a national and international outlook and focusing on the challenge of rebooting historically anthropized territories now at risk of being relinquished. In the light of these innovative tools’ stemming from the heritage, technology, and planning fields, all stakeholder perspectives, even with different nuances, converge on the fundamental issue of culture & community.