High school dropouts who return to school encounter many challenges. These obstacles increase the probability that a second dropout event will occur. This leaves leaders in Dropout Recovery programs with little ability to predict which students will stay in school and which are likely to leave again. However, what if a promising new scale could help predict which students would stick with it? In this quantitative correlation study, I examined the relationship between grit and re-engagement in high school dropout recovery. Results of the study indicated there was no relationship between the Grit-S scores of this non-traditional student population and the likelihood of re-engaging in their education. Although there is limited research on the relationship between grit and non-traditional student success, a thorough examination of past grit research does point towards positive relationships between grit and success in studies when the population has a history of academic success, for instance, military cadets and college undergrads. However, this study brought to light a more startling realization concerning assumptions about dropouts and grit. After examining the non-significant findings, I realized an attempt to harness a scale, such as grit, to predict a second dropout event perpetuates the use of labels. This directly contributes to the problem of deficit thinking associated with dropouts. An attempt to identify failure through a scale that is meant to judge staying power resulted in the realization that grit provides another pathway to deficit thinking.