This chapter focuses on trading strategies involving one-day-to-expiration put contracts, emphasizing the importance of adapting to current market conditions and implied volatility. It explores the risks associated with selling naked puts against the SPX, drawing parallels to the insurance industry while highlighting the necessity of a risk model. Additionally, the chapter analyzes historical market volatility and its influence on trading choices, stressing that significant market declines are often preceded by a buildup of volatility.