21st Century learning presents new challenges for teaching and measuring performance of complex cognitive skills such as communication critical thinking problem solving collaboration and career skills. Technologies for automated analysis of spoken and written language permit innovative approaches to support learning and assessment of 21st century skills. In this session the speakers will discuss technologies that are being applied across the range from individual learning to high stakes assessment. The speakers will provide specific examples of the application of the assessment approaches and results of their use. These technologies include: Automated assessment of scenario-based learning for writing skills comprehension critical thinking and problem solving. Methods to analyze effective written and oral communication for both core subjects and career skills Methods to analyze communication and teamwork in collaborative learning environments. The session will also describe ways that the technology can be used to provide realtime diagnostic information as well as track student progress over time for 21st century skills as well as core competencies.