One of the ways to frame goal engagement is through a simple but elegant two category model, distinguishing between promotion and prevention self-regulatory orientations. Prior research has shown that a prevention orientation is associated with better self-regulation relative to a promotion orientation (Chen et al. 2005; Freitas et al. 2002; Sengupta and Zhou 2007; Shah et al. 2002). The present research looks at why this occurs. Prior work would suggest that prevention-oriented people would prioritize resisting temptations as the strategy for goal attainment. However, there are reasons to believe that a prevention orientation may not necessarily entail active avoidance of temptation. Instead, we propose that a prevention orientation heightens the engagement with the goal overall, thus leading to self-regulation success. In particular, given prevention-focused individuals’ sensitivity to negative outcomes, the possibility of goal failure looms large for them. When faced with self-control dilemmas, their vigilance is heightened, and their attention focuses on what is most important—to engage with or approach the goal — rather than necessarily on avoiding temptations that may thwart successful goal pursuit. In contrast, promotion-oriented individuals focus on preventing errors of omission; this leads to a multifocal strategy of engaging in goal pursuit by both approaching the goal and countering temptation simultaneously. Despite the fact that multipronged approaches would, on the surface, seem to predict more successful outcomes, this approach may ironically undermine self-regulation.