By analysing the interrelations between the regulatory framework, organisational dynamics and gender politics, we assess the challenges for Gender Equality Bargaining in Chile. Several factors in the political arena drive an optimistic outlook: feminisation of trade unions, new working rights for women and a recent labour reform which introduces new mechanisms to foster gender equality through collective bargaining. We wonder how these progressive movements cope with an evolving and increasingly fragmented institutional and organisational context. The empirical work is based on interviews with policy experts, labour inspectors and female union leaders from the mining, retail and banking sectors. The findings suggest a significant disconnect between how these debates are framed on gender politics and what happens at the regulatory and organisational levels in terms of policy design, implementation and enforcement, which ultimately undermines GEB. The article contributes to a greater understanding of the interrelationships between the factors that constitute the opportunity structure and the importance of looking at different spheres of regulation. The paper concludes that progressive gender politics must be combined with more structural reforms to the industrial relations system to pursue more successful outcomes.