Although large-scale pretrained language models, such as BERT and RoBERTa, have achieved superhuman performance on in-distribution test sets, their performance suffers on out-of-distribution test sets (e.g., on contrast sets). Building contrast sets often requires human-expert annotation, which is expensive and hard to create on a large scale. In this work, we propose a Linguistically-Informed Transformation (LIT) method to automatically generate contrast sets, which enables practitioners to explore linguistic phenomena of interests as well as compose different phenomena. Experimenting with our method on SNLI and MNLI shows that current pretrained language models, although being claimed to contain sufficient linguistic knowledge, struggle on our automatically generated contrast sets. Furthermore, we improve models’ performance on the contrast sets by applying LIT to augment the training data, without affecting performance on the original data.