In practice, intuitive problem solving can go badly wrong. This chapter discusses its five specific pitfalls, based on real-life cases. First, a flawed problem definition almost invariably leads to irrelevant solutions. Second, most problem solvers start with a hypothetical solution in mind, which they tend to confirm instead of systematically challenging it. Third, picking the wrong framework when analyzing facts and data can be extremely misleading. Fourth, framing the problem space too narrowly hinders creativity and precludes the discovery of innovative solutions. Fifth, the ability to convince decision-makers is a double-edged sword: overselling the wrong solution might be even more harmful than underselling the right one. The 4S method presented in Chap. 3 helps overcome these five pitfalls.