This paper presents the submissions by TeamDr.Quad to the ACL-BioNLP 2019 shared task on Textual Inference and Question Entailment in the Medical Domain. Our system is based on the prior work Liu et al. (2019) which uses a multi-task objective function for textual entailment. In this work, we explore different strategies for generalizing state-of-the-art language understanding models to the specialized medical domain. Our results on the shared task demonstrate that incorporating domain knowledge through data augmentation is a powerful strategy for addressing challenges posed specialized domains such as medicine.