In the broader discussion on how to organize protection in the future of work, social partners sought to tackle the question of whether on-location platform workers are employees or freelancers. Extant literature investigating responses to platform work concentrates on institutions as main explanatory factor. While this provides valuable insights, it overlooks actors’ creativity and motivation as factors that allow to break away with existing constraints. This paper tackles such a shortcoming by developing a theoretical angle that looks at how uncertain actors actively shape institutions through learning processes. Using a qualitative methodology, it compares Danish and Dutch social partners’ responses to the question of platform workers’ contract classification. It finds that Danish social partners agreed on the need to shelter the centrality of collective bargaining for labour market regulation, while their Dutch functional equivalent stressed the urgency to re-think the way flexibility and protection are linked. Positions of Dutch social partners were considerably more polarized than in the Danish case. This work contributes to the i) scholarship on social partners and non-standard work in contemporary capitalist economies and ii) understanding of how the relationship between protection and flexibility is being re-defined in view of the future of work.