Emotion regulation is important for well-being. Recent work has begun investigating adaptive emotion regulation as a function of situation and strategy factors, where individuals vary in emotion regulation strategy use and efficacy. My first aim was to assess how emotion regulation success varies in naturalistic contexts. Study 1 found that the strategy reinterpretation differentially impacted affect based on perceived stress. There is also a need for experimental work that employs strategic training based on the interplay between situation and strategy factors, so my second aim was to deliver emotion regulation training in such adaptive matching patterns in young adults via implementation intentions training. Study 2 supported findings from Study 1 and implementation success positively predicted affect. Study 2 was not powered to investigate any unique effects of training content. The studies discussed here offer insight into how the interaction between emotion regulation and situational contexts can impact well-being.