Unscaffolded problem-solving before receiving instruction cangive students opportunities to entertain their exploratory hy-potheses at the expense of experiencing initial failures. Priorliterature has argued for the efficacy of such Productive Fail-ure (PF) activities in preparing students to “see” like an expert.Despite growing understanding of the socio-cognitive mecha-nisms that affect learning from PF, the necessity of success orfailure in initial problem-solving attempts is still unclear. Con-sequently, we do not know yet whether some ways of succeed-ing or failing are more efficacious than others. Here, we reportempirical evidence from a recently concluded classroom PF in-tervention (N=221), where we designed scaffolds to explicitlypush student problem-solving towards success via structuring,but also radically, towards failure via problematizing. Our ra-tionale for explicit failure scaffolding was rooted in facilitatingproblem-space exploration. We subsequently compared thedifferential preparatory effects of success-driven and failure-driven problem-solving on learning from subsequent instruc-tion. Results suggested explicit failure scaffolding during ini-tial problem-solving to have a higher impact on conceptual un-derstanding, compared to explicit success scaffolding. Thistrend was more salient for the task topic with greater difficulty.