The idea that increased levels of extraversion are beneficial to well-being is widespread. Drawing on the idea that behaving discordant to one's trait level is demanding and effortful to maintain, and that repeated taxations of one's self-regulatory resources are unpleasant, we examined the relationship between cumulative counterdispositional extraversion and positive feelings. In two experience-sampling (ESM) studies, participants repeatedly rated their level of state extraversion and positive feelings. Results revealed that cumulative positive deviations from one's trait extraversion level were positively associated with positive feelings, whereas cumulative negative deviations were negatively associated with positive feelings. This confirms the idea that, also when looking at cumulative instances of extraversion-related behaviors, higher levels of extraversion go hand in hand with higher levels of positive feelings.