AbstractRecent studies have shown that pre-trained contextual word embeddings, which assign the same word different vectors in different contexts, improve performance in many tasks. But while contextual embeddings can also be trained at the character level, the effectiveness of such embeddings has not been studied. We derive character-level contextual embeddings from Flair (Akbik et al., 2018), and apply them to a time normalization task, yielding major performance improvements over the previous state-of-the-art: 51% error reduction in news and 33% in clinical notes. We analyze the sources of these improvements, and find that pre-trained contextual character embeddings are more robust to term variations, infrequent terms, and cross-domain changes. We also quantify the size of context that pre-trained contextual character embeddings take advantage of, and show that such embeddings capture features like part-of-speech and capitalization.