Developing methods to adversarially challenge NLP systems is a promising avenue for improving both model performance and interpretability. Here, we describe the approach of the team “longhorns” on Task 1 of the The First Workshop on Dynamic Adversarial Data Collection (DADC), which asked teams to manually fool a model on an Extractive Question Answering task. Our team finished first (pending validation), with a model error rate of 62%. We advocate for a systematic, linguistically informed approach to formulating adversarial questions, and we describe the results of our pilot experiments, as well as our official submission.