Over the past two years, the Industrial Relations and Social Dialogue for an Economy and Society 4.0 (IRESDES 4.0) project has dived into the developments of smart working and digital skills. Specifically, the project consortium has analysed the impact of collaborative labour agreements and other social dialogue practices in ensuring digital skills development within small and medium-sized enterprises (SMEs) and how the presence of contractual ambiguity is still pending over innovative working options.