Available evidence from separate lines of event-related potential (ERP) research has highlighted the role of expectations and emotion regulation on emotional processing by revealing that (i) expectations can alter emotional responses, and (ii) the instructed use of emotion regulation strategies may modulate emotional responses. Yet, little is known about the interplay between expectations and habitual emotion regulation strategies prior to and at the onset of an emotional event. The present study aimed to investigate this potential relationship. Participants completed an affective-cueing task consisting of cues (red squares and blue circles) signaling the likely valence of upcoming target images (negative or neutral). This task allowed us to examine the impact of expectations at 2 temporal stages, Cue Interval and Target Interval, by measuring the late positive potential (LPP) as an index of emotional processing. Habitual use of emotion regulation strategies was assessed through the Emotion Regulation Questionnaire (ERQ), which measures the use of cognitive reappraisal and expressive suppression in everyday life. In the Cue Interval, LPP amplitude was greater for negative versus neutral cues (p < .001). In the Target Interval, LPP amplitude was greater for negatively cued versus neutrally cued targets, regardless of target valence (p = .003). ERQ reappraisal, but not suppression, negatively correlated with LPP modulation as a function of cue valence during both intervals (ps < .05). These findings provide novel insights regarding the interplay between expectations and habitual emotion regulation in emotional processing both prior to and at the onset of an emotional event.