During August 2025, Sergey Prigogin enhanced the JetBrains/intellij-community repository by implementing content removal query handling in ToolWindowHeadlessManagerImpl. Leveraging event-driven programming and Java, Sergey introduced listener-based validation to align the content removal lifecycle with ContentManagerImpl, addressing a longstanding discrepancy that previously risked invalid removals in headless scenarios. This work improved the reliability and consistency of internal APIs for content management, particularly in environments without a graphical interface. By focusing on robust software development practices and clear commit documentation, Sergey’s contribution laid a solid foundation for future enhancements in tool window content handling and cross-module integration within the codebase.