In this work, we investigate how applying human-like characteristics to customer service chatbots can influence retail outcomes. This is an important managerial question as creating effective chatbot experiences through messaging platforms has proven difficult for organizations. Often, chatbot developers apply characteristics such as giving a chatbot a human name, adding humor, and so on, without knowing how these features influence end user behavior. Implementing a field experiment in collaboration with a dual channel clothing retailer based in the United States, we automate a used clothing buy-back process, such that individuals engage with the retailer's autonomous chatbot to describe the used clothes they wish to sell, obtain a cash offer, and (if they accept) print a shipping label to finalize the transaction. We provide evidence that, in this retail setting, anthropomorphism is beneficial for transaction outcomes, but that it also leads to significant increases in consumers’ sensitivity to the offer amount. We argue that the latter effect occurs because, as a chatbot becomes more human-like, consumers shift to a fairness evaluation or negotiating mindset.