Tail Risk Management with Puts and Trend Following: A CVaR Framework for Crashes and Drawdowns

Tail-risk management is not only an instrument-selection problem. It is an allocation problem across loss mechanisms: abrupt crash states, volatility repricing, and persistent drawdowns require different forms of protection. This paper develops a continuous-time CVaR framework that places two common protection sleeves -- long out-of-the-money put options and systematic trend-following overlays -- inside one coherent tail-risk mandate. The option sleeve is modeled as a marked-to-market traded asset, so premium drag, diffusion exposure, and jump repricing enter through its physical return process rather than through inconsistent terminal-payoff accounting. The resulting Markov state contains wealth, spot, stochastic variance, and an exponentially weighted log-return signal, and we derive the associated Hamilton--Jacobi--Bellman equation in viscosity form. The main analytical separation is temporal: convex insurance reprices immediately on jump impact, whereas trend following is late on the first shock because its signal must cross zero, but becomes increasingly defensive during persistent drawdowns without requiring fresh option premium. We then give sufficient and local conditions for an interior hybrid allocation, derive a CVaR policy-gradient identity, and introduce a four-axis diagnostic layer separating conditional convexity, tail-event reliability, non-stress carry, and drawdown persistence. Stylized Monte Carlo experiments illustrate the mechanism: fixed equal-weight hybrids and grid-optimized hybrids reduce terminal CVaR relative to either pure sleeve in the reported regimes, while the exact weight location remains calibration-dependent. The contribution is a transparent risk-management framework for deciding how much convex crash protection and how much signal-driven drawdown protection a mandate should hold.