In software development, many documents (e.g., tutorials for tools and mobile application websites) contain screenshots of GUIs to illustrate functionalities. Although screenshots are critical in such documents, screenshots can become outdated, especially if document developers forget to update them. Outdated screenshots can mislead users and diminish the credibility of documentation. Identifying screenshots manually is tedious and error-prone, especially when documents are numerous. However, no existing tools are proposed to detect outdated screenshots in GUI documents. To mitigate manual efforts, we propose DOSUD , a novel approach for detecting outdated screenshots. It is challenging to identify outdated screenshots since the differences are subtle and only specific areas are useful to identify such screenshots. To address the challenges, DOSUD automatically extracts and labels screenshots and trains a classification model to identify outdated screenshots. As the first exploration, we focus on Android applications and the most popular IDE, VS Code. We evaluated DOSUD on a benchmark comprising 10 popular applications, achieving high F1-scores. When applied in the wild, DOSUD identified 20 outdated screenshots across 50 Android application websites and 17 outdated screenshots in VS Code documentation. VS Code developers have confirmed and fixed all our bug reports.