10/27/2026
Royal Palm Beach, Wellington, and Loxahatchee Tax Payers - Tax-loss harvesting season is here, and this is the rule people get wrong most often.
The idea is sound: sell a position at a loss, use the loss against gains, and keep your portfolio roughly where you want it. Losses offset capital gains without limit, then up to $3,000 of ordinary income, with the rest carrying forward indefinitely.
The wash sale rule disallows the loss if you buy a substantially identical security within 30 days β and that's 30 days before the sale as well as 30 days after. A 61-day window with the sale in the middle. Buying a position in early December and selling a different lot of it at a loss two weeks later can trip it.
Two details that cause real problems:
It crosses accounts. A purchase in your IRA, or in a spouse's account, can disallow a loss taken in your taxable account. Automatic dividend reinvestment is a frequent and invisible culprit.
A disallowed loss isn't gone β it's added to the basis of the replacement shares. But it's deferred, which defeats the point of the harvest.
One more thing: as the law currently stands, the wash sale rule applies to securities and not to digital assets, though legislation to change that has been proposed. Worth confirming before relying on it.