Cognitive reappraisal is an emotion regulation strategy that involves reinterpreting the meaning of an event or its outcome to change its emotional trajectory. In this study, we examined how cognitive reappraisal affects both emotional experience and memory outcomes. We also examined whether these outcomes are modulated by participants' self-reported success at generating reappraisals. To do this, we asked participants to use situation-focused reappraisals to decrease their emotional response to some negative images and to passively view other negative images while facial electromyography (EMG) was recorded. After each trial, participants rated the image's emotional valence and arousal. During reappraisal trials, participants also self-reported their success in generating a reappraisal. One week later, memory was assessed with a surprise free recall test followed by a recognition test. Compared with images that were passively viewed, participants (N = 42) rated the successfully reappraised images as lower in arousal and less negative in valence. Meanwhile, there was an emotional cost associated with failures to generate reappraisals; participants rated these images as higher in arousal and more negative in valence. No similar effects emerged for the EMG ratings. In contrast to these emotional outcomes, a different pattern emerged for the memory outcomes. Instructions to reappraise led to enhanced recall and recognition and to greater memory confidence regardless of whether or not participants successfully generated the reappraisals. Taken together, these results suggest that trying, but failing, to generate a situation-focused cognitive reappraisal may be detrimental. In these situations, people feel worse but remember the situation well. (PsycInfo Database Record (c) 2020 APA, all rights reserved).