Though important advances have occurred in recent years, governments are regularly surprised by the emergence of crises and still struggle to identify and understand them. This chapter examines the challenges of early warning and sense-making associated with strategic crises. It explores the multiple contexts - group, organisational, and political - in which leaders and their advisers are embedded. These contexts enable and constrain leaders and their advisors. The role of current and emerging information and communications technology (ICT) is discussed in relation to finding ways to harness technology to increase sense-making capacity and identify potential vulnerabilities and risks. In addition, problems of effectively managing expertise, information, and knowledge with regards to early warning and crisis management are examined. The chapter concludes by presenting a set of critical topics that require further capability development and policy reform efforts.