Extreme market events, once perceived as statistical outliers, have become a central concern for investors. The persistence of sharp drawdowns and volatility spikes demonstrates that the cost of ignoring tail risks is not tolerable for long-term portfolio resilience. While diversification can mitigate ordinary fluctuations, it often fails when markets move in unison under stress. This makes explicit protection against severe downside events not just desirable but necessary. Tail hedging addresses this need by providing a structured defense against the most damaging scenarios, ensuring that portfolios remain robust when traditional risk management tools fall short. Using VIXY ETF, we will present and test a range of hedging strategies designed to protect portfolios under stress. By applying robust testing frameworks, we aim to evaluate how different implementations of VIXY ETF-based tail hedges perform across a variety of market environments, highlighting both their strengths and inherent trade-offs.