Since the mid-1970s, research shows that less-disadvantaged individuals more frequently access social policy schemes when compared to their more-disadvantaged counterparts, a phenomenon called the Matthew effect. Through two indepth case studies, based on 60 semi-directive interviews, and document analysis, this study aims to more fully understand the mechanisms leading to a Matthew effect in Swiss Vocational Education and Training (VET) programmes for disadvantaged youth. Indeed, education is key to post-industrial labour markets access, and VET appears to facilitate schoolto-work transitions. A Matthew effect in this policy field might thus lead to particularly detrimental repercussions, and public authorities should be especially eager to contain it. Nevertheless, findings show that, under certain conditions, decision-makers push frontline-workers into cream-skimming practices, causing a Matthew effect. Additionally, structural challenges also lead to a Matthew effect, highlighting the general difficulty of the very mandate: (re-)inserting highly disadvantaged individuals into selective markets. Indeed, in contexts of tight public budgets, service oriented modern Welfare States tread a fine line between empowering and prioritising beneficiaries. Dealing with complex target groups, it seems crucial whether the rationale driving public authorities is more oriented towards credit-claiming or problem-solving: the former increasing and the latter decreasing the incidence of Matthew effects.