Emerging events, such as the COVID pandemic and the Ukraine Crisis, require a time-sensitive comprehensive understanding of the situation to allow for appropriate decision-making and effective action response. Automated generation of situation reports can significantly reduce the time, effort, and cost for domain experts when preparing their official human-curated reports. However, AI research toward this goal has been very limited, and no successful trials have yet been conducted to automate such report generation. Pre-existing natural language processing methods, large language model based text generation, and information retrieval techniques are insufficient to identify, locate, and summarize important information, and lack detailed, structured, and strategic awareness. We propose SmartBook, a novel task formulation targeting situation report generation, which consumes large volumes of news data to produce a structured situation report with multiple hypotheses (claims) summarized and grounded with rich links to factual evidence. We realize SmartBook for the Ukraine-Russia crisis by automatically generating intelligence analysis reports to assist expert analysts. The machine-generated reports are structured in the form of timelines, with each timeline organized by major events (or chapters), corresponding strategic questions (or sections) and their grounded summaries (or section content). Our proposed framework automatically detects realtime event-related strategic questions, which are more directed than manually-crafted analyst questions, which tend to be too complex, hard