The use of grade retention and social promotion among middle school students in Missouri was analyzed in this study. Quantitative data were gathered from 115 middle school principals who completed an online survey regarding grade retention and social promotion. Qualitative data were collected from five middle school principals in southwest Missouri who participated in an interview. The five principals selected students from their respective schools to participate in an interview where additional qualitative data were collected. The students who were selected had been retained or socially promoted while in grades six through eight. Data collected from the survey showed 68% of participating principals retained students, and 78% of participating principals socially promoted students. The data from the survey also revealed the participating principals felt it was important to involve teachers and parents when retaining or socially promoting students. A student’s grades were the biggest contributor to grade retention, and a student’s age was the biggest factor when choosing to socially promote. The retained students who were interviewed had a more positive attitude than the socially promoted students. The retained students who were interviewed had seen improvement in their grades and attendance from the previous year, whereas only half of the socially promoted students had seen improvement in their grades and attendance. Despite what most research yielded regarding negative long term effects of grade retention, middle school principals continue to use this option. However, the retained students who were interviewed showed improvement and had a positive outlook on their future.