The hypothesis that cognitive reappraisal will have different effects on emotion as a function of regulatory goal and the timing with which reappraisals are enacted within an emotion episode was tested. Forty-one participants reappraised situations depicted in unpleasant pictures by imagining those situations getting worse (increase), staying the same (maintain), or getting better (decrease). Reappraisal instructions were delivered 2 s before (anticipatory) or 4 s after (online) picture onset. Measures of rated unpleasantness, expressive behavior (corrugator muscle activity), heart rate (HR), and electrodermal activity (EDA) were collected. Increase reappraisals produced higher rated unpleasantness, corrugator muscle activity, HR, and EDA relative to maintain reappraisals. For corrugator muscle activity and EDA, the effect of increase reappraisals was only apparent when enacted online. Decrease reappraisals produced lower rated unpleasantness relative to maintain reappraisals but had no effect on expressive behavior or autonomic physiology. The effect of decrease reappraisals did not depend on when reappraisal was enacted. These data underscore the importance of regulatory goals and the impact of regulatory timing as a moderator of emotion regulatory success within an emotion episode.