The Italian 2014-2020 Partnership Agreement stipulated the institution of a Steering Committee for the coordination and monitoring of the interventions under Thematic Objectives (TO) 11 (Strengthening Administrative Capacity) and 2 (Digital Growth) implemented in all Italian Regional and National ERDF and ESF Operational Programmes (OPs). The aim of the Committee is to promote the integration and synergy between the interventions implemented under these TOs and between different OPs, to prevent overlaps and fragmentation, and to ensure the most effective deployment of resources. The Committee was formally established at the beginning of 2015. Since 2016 it has implemented a monitoring activity aimed at developing a comprehensive picture of the state of TO11 and TO2 interventions. This article summarises the main findings of the Committee’s last monitoring report, which was published in May 2018. The TO11-TO2 Steering Committee is a unique experience across Europe and its monitoring activity has shed new light on the strengths and weaknesses in implementing TO11 and TO2, and highlighted a number of lessons whose validity arguably spans beyond Italy’s borders. They include, amongst others, the need for improved strategic framing for TO11 interventions, in order to make them more structural, systematic and long-term; the importance of deploying TO2 in a way that goes beyond updating already existing technological solutions, and the need to strengthen the synergies between TOs, funds and programmes beyond the strategic level.