The challenges of insuring major, often international, sporting and entertainment events are multi-faceted, and the insured values eye-watering. Inflation has impacted ticket prices, travel and accommodation costs and is likely to continue to drive such values upwards. Contingency underwriters need to assess an increasingly complex set of interconnected risks, including security, weather, geopolitics, cyber and logistics. The market has responded to these challenges with increasingly integrated risk assessment procedures, more comprehensive policies and more sophisticated pricing models. As we look forward to mega events such as the 2026 FIFA World Cup and the 2026 Winter Olympics, contingency insurers will need to continue to leverage data and analytics, and to work with third party security, environmental and other specialists, to ensure they have the granular detail necessary to write these risks sustainably.