Despite great attention and numerous efforts across countries to reduce school dropout, it remains a persistent challenge. One such initiative, named New Possibilities, launched by the Norwegian Ministry in 2010, was a nationwide, flexible program aimed at providing intensive training to poor achievers during the last months of 10th grade, before they started upper secondary school. Differentiated analyses of grade development indicate that participating students with the very lowest grades improved, while those with moderate grades did worse than nonparticipating peers. The heterogeneity of the participating students is discussed with attention to the flexibility of the intervention and local discretion. Differences in local interpretations of the purpose of the initiative include responses to ambiguities, conflicting values, contradictory policy demands, and a lack of identification of core elements pertaining to the initiative.