Agile tools like Jira excel at tracking work as it moves from "To Do" to "Done". But when we rely on tickets to capture context and decisions made during task implementation, the issue tracker also unintentionally becomes a store of knowledge. Communicating solely through tickets eliminates nuance and empathy, and makes work more siloed and inhuman. This talk explores common pitfalls, strategies for managing knowledge outside of Jira, and techniques for using AI to reclaim and reorganize that knowledge into a more human-centric workflow.