The passage to middle school has been identified as a confusing period for adolescents, involving a series of major transitions. A new variable that permeates these already lofty transitions is the firm entrenchment of Generation Alpha in the middle grades classroom, a cohort that includes anyone born from 2010 onward, making them the first generation born and shaped entirely in the twenty-first century. The purpose of this study was to explore the attitudes and perceptions of current middle school teachers across Indiana, Kentucky, and Ohio toward their Gen Alpha students so as to uncover the concrete issues these teachers encounter as they work with this undeniably unique cohort. A total of 139 teachers responded to the researcher-generated electronic survey, which was coded inductively and analyzed for content. The feedback points to a cohort that is digitally literate with great adaptability, but also a cohort that exhibits delayed social development and a myriad of global concerns. These factors all have implications for the ways they learn, interact, and function in the middle school classroom.