Today more than ever before, online writing (e.g., emails, texts, and social media posts) has become a primary means of communication. Because written communication lacks human nonverbal cues (e.g., voice), people frequently struggle to distinguish whether they are interacting with a human or chatbot online. The current research suggests a novel way to humanize writers: typographical errors (“typos”). Across four experiments (N = 1,253) that used ambiguous conversational counterparts (e.g., customer service agents that might be bots), communicators who made and subsequently corrected a typo, rather than making no typo or not correcting a typo, appeared more humanlike. Respondents consequently believed that the communicator was warmer and were more likely to disclose personal information to the communicator. These findings provide insight into when people are willing to share their personal data online. We discuss theoretical implications for humanization and practical implications for Internet privacy and building trust in organizations.