This chapter addresses tail risk hedging using options, focusing on how portfolio managers can proactively protect against rare but severe market events. The case demonstrates how portfolio managers can cushion portfolios against extreme downside risks while preserving exposure to the market upside by structuring and implementing options-based hedging strategies. A hypothetical scenario examines the practicalities of using OTM put options for hedging an equity portfolio, providing insight into their costs and performance under adverse conditions.