Adolescence and the onset of puberty is a time period of physiological and behavioral changes that include a heightened reward sensitivity, but underdeveloped cognitive control. Cognitive control involves monitoring for salient stimuli and recruiting control to adapt behavior advantageously to reach a specific goal and is supported by the three domains of executive functioning (EF): inhibitory control, set-shifting, and working memory. Proactive control is engaged after an informative cue in preparation for an upcoming stimulus, while reactive control can be employed when preparation is not possible and you need to respond to a stimulus. Oscillations in the theta frequency (4-8Hz) during both cue presentation and stimulus presentation are implicated in proactive and reactive control processes. While reward has been shown to upregulate proactive control in adults, little work has assessed how reward influences theta oscillations during both proactive and reactive control throughout adolescence and pubertal development. Further, no work has sought to understand how EF abilities bolster reward-related changes in proactive or reactive control. Here, 68 adolescent males (Meanage=13.61, SDage=2.52) aged 9 – 17 years old completed a rewarded cued flanker paradigm while electroencephalogram (EEG) was collected. They also completed tasks from the NIH toolbox that tap the three EF domains. Behaviorally, reward hindered performance on proactive trials, particularly in mid-puberty, while enhancing performance on reactive trials. Reward was associated with increases in cue-locked theta power, but with overall reductions in cue-locked theta ICPS. Stim-locked theta power increased on reactive trials with increasing age, while stim-locked theta ICPS peaked in mid-adolescence for rewarded trials. Increased cue theta power was associated with worse performance on proactive trials. On proactive trials, adolescents with low levels of inhibitory control experience more reward-related interference, while reward-related interference was mitigated by better set-shifting abilities only in younger and older adolescents. In conclusion, reward differentially impacts proactive and reactive control throughout adolescent development and EF influences the impact of reward on proactive control throughout adolescence.