Unscaffolded problem-solving before receiving instruction can give students opportunities to entertain their exploratory hypotheses at the expense of experiencing initial failures. Prior literature has argued for the efficacy of such preparatory activities in preparing students to learn from instruction. Despite growing understanding of the underlying cognitive mechanisms, the pedagogical value of success or failure in initial problem-solving attempts is still unclear. We do not know yet whether some ways of succeeding or failing are more efficacious than others. We report empirical evidence from a classroom intervention (N = 221), where we designed scaffolds to explicitly push student problem-solving toward success via structuring, but also toward failure via problematizing. Our rationale for explicit failure scaffolding was rooted in facilitating problem-space exploration. We subsequently compared the differential preparatory effects of success-driven and failure-driven problem-solving on learning from follow-up instruction. Results suggested that failure-driven scaffolding (nudging students to generate suboptimal solutions) and success-driven scaffolding (nudging students to generate optimal solutions by giving them heuristics with low specificity) had similar outcomes on posttest assessments of conceptual understanding. Students exposed to failure-driven scaffolding, however, demonstrated higher quality of constructive reasoning. These trends were more salient for the learning concept with greater difficulty.