Brace for significant market volatility on Friday: A $5.15 trillion worth of options on the S&P 500 are set to expire on June 19th, the largest monthly expiration on record. This is led by the S&P 500 index options, which account for $4.84 trillion of the total. The remaining $307 billion consists of options on the S&P 500 ETF, SPY. As a result, a large portion of the options tied to the Iran conflict, bought by investors as protection against geopolitical risk, are set to expire on Friday. Once that protection expires, the market will lose a key source of stabilizing hedging flows, increasing the risk of larger swings in either direction. Markets are set for a volatile end to the week.(The Kobeissi Letter)