Automatic grading models are valued for the time and effort saved during the instruction of large student bodies. Especially with the increasing digitization of education and interest in large-scale standardized testing, the popularity of automatic grading has risen to the point where commercial solutions are widely available and used. However, for short answer formats, automatic grading is challenging due to natural language ambiguity and versatility. While automatic short answer grading models are beginning to compare to human performance on some datasets, their robustness, especially to adversarially manipulated data, is questionable. Exploitable vulnerabilities in grading models can have far-reaching consequences ranging from cheating students receiving undeserved credit to undermining automatic grading altogether—even when most predictions are valid. In this paper, we devise a black-box adversarial attack tailored to the educational short answer grading scenario to investigate the grading models’ robustness. In our attack, we insert adjectives and adverbs into natural places of incorrect student answers, fooling the model into predicting them as correct. We observed a loss of prediction accuracy between 10 and 22 percentage points using the state-of-the-art models BERT and T5. While our attack made answers appear less natural to humans in our experiments, it did not significantly increase the graders’ suspicions of cheating. Based on our experiments, we provide recommendations for utilizing automatic grading systems more safely in practice.