Catecholamines exert significant influence over various cognitive functions, and their modulation via methylphenidate (MPH), a reuptake inhibitor, has been investigated in several studies. The presented work examines the effects of pharmacological manipulation using MPH on two specific cognitive processes: event file binding in response inhibition and event segmentation behavior. Examining the effects of MPH on event file (re)binding processes in response inhibition, we find that MPH enhances overall inhibition performance while diminishing binding effects. However, this effect exhibits considerable variability, consistent with findings from diverse studies and clinical applications, where MPH-based medication responses in conditions such as ADHD vary widely. Subsequent analysis of task-unrelated theta band modulability reveals that individuals we categorized as "high modulators" demonstrate benefits in both inhibition and binding, whereas "low modulators" only experience improvements in inhibition. Regarding event segmentation behavior, which reflects the automatic partitioning of continuous streams of information, we observe that the relationship between changes in the environment and event segmentation behavior is influenced by MPH administration. Notably, this effect is contingent upon the familiarity with the stimulus material, indicating that situational context plays a crucial role in shaping cognitive responses. These findings provide nuanced insights into the effects of MPH-induced catecholaminergic modulation on cognitive processes, while also highlighting the relevance of individual differences and contextual factors in research regarding the neurobiological underpinnings of cognitive functions.