Research on emotion regulation (ER) has shifted from focusing on the static to the flexible use of ER strategies in response to environmental demands, emphasizing the importance of strategy-situation fit. Despite the growing theoretical popularity and importance of this concept, empirical evidence remains scarce. To address this gap, we examined the role of negative affect in moderating ER effectiveness because research suggests that as negative affect increases, people tend to prefer distraction over reappraisal. We re-analyzed twelve ambulatory assessment datasets (1,511 participants with 161,513 measurement occasions) collected from predominantly Caucasian undergraduate psychology students. Using meta-analytic techniques, we did not find any evidence for strategy-situation fit, i.e., choosing distraction in high-intensity situations and reappraisal in low-intensity situations, was not significantly associated with positive affect, negative affect, or depressive symptoms. Given these null results, we discuss current problems with how strategy-situation fit is currently operationalized to advance research on this important topic.