This chapter investigates the potential negative signalling effects of unemployment and participation in active labour market measures in Greece and Norway. A vignette experiment directed at recruiters and employers is applied. Our findings show that negative signalling effects of unemployment are more pronounced in countries where the macroeconomic context is positive and unemployment rates – including the youth unemployment rate – are low. What is also significant is that participation in active labour market policies is not perceived very positively in these cases. Our study shows that participating in ALMPs is perceived in a more positive way in a context of high unemployment, such as in Greece, whereas it might have a negative effect in a context where labour demand is high, such as in Norway. Our findings call for rethinking and, most importantly, contextualizing active labour market policies, taking into account national and sectorial specificities.