We plan to assemble panellists from a range of U.S. government agencies such as the U.S. Army, the U.S. Food & Drug Administration, the Federal Aviation Administration, and Sandia National Labs to share the issues and challenges they face in developing, applying, studying and regulating advanced automation, artificial intelligence, machine learning in complex settings. These technologies are proposed for use in military operations, civilian aviation, railways, patient and physician-facing medical devices, and many others. While some themes are common across contexts, challenges vary depending on context, intended use, and intended user. Panelists will discuss the challenges related to integrating advanced automation in their domains, risks they anticipate, and human capabilities that should be preserved and supported.