U.S. equity markets face a quarterly “triple-witching” event on Friday, when roughly $6.5 trillion in notional options are scheduled to lapse in the largest June expiration on record. Goldman Sachs estimates the batch includes about $4 trillion of S&P 500 contracts and $925 billion linked to individual shares, while the overall figure equals 9.6% of the Russell 3000’s market value. The expiry lands one session after the Juneteenth holiday—marking the first post-holiday triple-witching since 2000—and leaves traders with less time than usual to rebalance positions. Derivatives analytics firm Asym 500 also highlights record activity in same-day, zero-day-to-expiration options, underscoring the potential for abrupt repositioning once contracts roll off. Strategists at Citi and Goldman say the event could unwind the “pinning” effect that has kept price moves muted since early May, possibly amplifying swings in the S&P 500, which has been hovering near the 6,000 level. Although past quarterly expirations have not always sparked outsized volatility, market-makers may need to adjust hedges aggressively, making the period immediately after Friday’s close a key test of market resilience.