To understand the impact of incentivized test/retest scenarios – where students are afforded an opportunity to retest for an incentive – in design education settings, this study examines participants brain activity using electroencephalography (EEG) during stressful retest situation. This study mimics educational scenarios where students are afforded an opportunity to retest after a first attempt. Twenty-three student participants were randomly divided into two cohorts: control and experimental. Participants were asked to complete a preliminary questionnaire self-assessing their ability to handle stressful situations. Both cohorts were subsequently asked to complete the typing test and complete an Emotional Stress Reaction Questionnaire (ESRQ), indicating their emotional response during the typing test. The participants were subsequently asked to complete the typing test and accompanying ESRQ a second time. However, prior to the second test, the participants in the experimental cohort were incentivized with a monetary reward for improving their typing speed. This stimulus is used to increase the already stressful situation for the experimental cohort and examine changes in brain activity when the “retest” is incentivized. The results indicate no significant changes in brain activity, emotions, or typing performance for the control group. However, the experimental group showed an increase in EEG sensor activity; specifically, the sensors that control vision and emotion. The experimental group's performance was correlated to their emotional responses, rather than their EEG sensor data. Additionally, the experimental groups' positive emotions were increased for the incentivized typing test. The findings provide recommendations for educational retests practices.