The article examines the adoption of Flexicurity principles in Portugal and Greece during 2006–2009. Despite the similar conditions between the two cases and common EU stimulus, the process and final outcomes in the reform of their employment protection systems differed. In Portugal, the government persevered and implemented a reform in line with Flexicurity principles. By contrast, the Greek government initially favoured Flexicurity and initiated a reform process of the legal framework; however the reform was halted. The article explains this divergence by combining the insights of Europeanization and Varieties of Capitalism literatures. It is argued that in cases of Mixed Market Economies, ‘misfit’ with EU stimuli is a necessary, but not sufficient condition for institutional change. Instead, reforms depend on union structure and the existence of policy entrepreneurs favouring reform, which explains the divergent reform paths.