The paper builds on the case of the design and implementation of the National Information System for School Buildings in Italy. The project is one of digitalisation of the public sector and involves several layers of territorial governments (the State Department for Education, regional and local governments) and ICT experts, and is becoming a tool for policy making in the field. Nonetheless, the programme was initially designed with a top-down approach immediately stuck. Its effective implementation only took place some years later by downsizing policy design and allowing regions to implement those digital solutions which, in the meanwhile, had been designed and implemented from the bottom-up. The paper draws from the case study theoretical considerations about the importance of where policy learning happens and the strategies that policy makers may adopt in case of policy failure in order to re-establish the conditions for effectiveness.