A recent study illustrated that the educational attainment of Latina/o students has been dismal during the past decade and that many Latinas/os continue to "fall through the cracks" of the educational pipeline. Through storytelling, I juxtapose my educational trajectory as a high school graduate with that of my third-oldest brother, who "fell through the cracks" of the educational pipeline as an underclassman in high school. I provide examples of how being reprimanded for minimal misconduct negatively impacted my older brother's overall school experiences, which ultimately prevented him from finishing high school despite his potential to succeed.