Cognitive reappraisal is a widely used emotion regulation strategy that involves changing the meaning of a situation to alter which emotions we feel, and for how long or intensely we experience them. Research has linked cognitive reappraisal success with improved social functioning and well-being, as well as fewer psychopathological symptoms. The present work examined whether preparatory regulation cues facilitated success in generating cognitive reappraisals and if success or failure in implementing preparatory cognitive reappraisals was differentially associated with how events are experienced and subsequently remembered. To achieve these aims, participants were presented with pictures of negative scenes and were instructed to either decrease their emotions with cognitive reappraisal or to let their emotions unfold naturally prior to making emotional ratings (i.e., arousal, success in generating reappraisals). Importantly, across experiments participants were given either preparatory regulation cues (cognitive reappraisal, view) prior to the negative scene, preparatory regulation cues paired with emotional information about the upcoming negative scene (moderate, intense), preparatory emotional information prior to online regulation, or no preparatory cues prior to online regulation. Following a 24-hour delay, participants completed a recognition memory test. The results revealed no evidence that preparatory regulation cues, relative to online reappraisals, were associated with greater success in generating cognitive reappraisals, nor with improved reductions in self-reported arousal ratings of the negative scenes. Interestingly, preparatory regulation, relative to online regulation was associated with enhanced memory accuracy for negative scenes which converges with prior neuroimaging findings and suggest that preparatory cues can facilitate successful memory. One implication from these findings is that preparatory cues may not improve our ability to regulate our emotions but may enhance the memorability of these events. Whether or not this outcome is beneficial may depend on the goals of the situation, such that preparatory cues may be ideal when our primary objective is for individuals to remember information opposed to being able to change how they feel about the events. Future work can expand upon these findings by investigating different types of preparatory reappraisal strategies that may benefit our ability to regulate our emotions.