06/24/2026
π Most tax-loss harvesting happens in December. That's also when it's least effective.
The mechanics:
Tax-loss harvesting means selling a position at a loss to realize the loss for tax purposes β using it to offset realized gains (and up to $3K of ordinary income annually for individuals).
The wash sale rule: if you buy a "substantially identical" security within 30 days before or after the sale, the loss is disallowed for tax purposes.
Why mid-year is structurally better:
β‘οΈ Wash sale window: a loss harvested in June clears fully by July, well before year-end portfolio rebalancing
β‘οΈ Replacement window: you can rotate into a non-identical replacement for 31+ days, then move back if desired
β‘οΈ Strategic time horizon: losses harvested early offset gains realized later in the year, with full coordination
β‘οΈ Avoids the December rush, when illiquid positions become impossible to exit at reasonable prices
This is portfolio architecture, not last-minute scrambling. The advisor who only mentions loss harvesting in November is reactive. The advisor who modeled your gain/loss position in June is proactive.
π· We coordinate tax-loss harvesting with portfolio managers year-round.