In a cross-national project, 14 neighborhoods from Germany, Austria and Switzerland were accompanied on their way to digitally supported neighborhood work. This paper discusses general requirements, choosing a suitable digital tool, the implementation process as well as the challenges faced by the various stakeholders. The following factors have been found to play a major role in sustainable neighborhood work: good fit with overall development strategy, interplay between online neighborhood work and physical interactions, strong existing neighborhood management structures, strategic planning of digitalization activities, start-up funding for innovation activities, and above all, the presence of a committed person or team as well as interesting content to attract users. Depending on the neighborhood, self-managed and individualistic solutions are preferred to generic and/or commercial solutions. There is no ‘fit-for-all’ path to sustainable digitally supported neighborhoods.