Sentry is a crucial tool for data teams, enabling high-quality leads and tailored marketing campaigns, as well as informing business decisions such as Sentry pricing and feature roadmap. Apache Airflow is used for executing data pipelines, but its built-in log interface lacks context, making issue resolution challenging. A new plugin, sentry-airflow, has been introduced to address this issue by collecting, handling, and reporting errors that occur within Airflow tasks. The plugin can be easily integrated into Airflow via a drop-in solution requiring only two steps: placing it in the plugins folder and setting an environment variable. Errors are reported with useful tags, including dag_id, task_id, execution_date, and operator, and also include upstream DAG tasks as breadcrumbs for additional insight. The plugin is available for use and continuously improving, with support engineers available to help with feedback, feature requests, or usage assistance.