Thinking About Taking Year End Tax Losses? Don’t Make These Mistakes

Given the stock market’s performance this year, you may be thinking about taking some losses—otherwise known as tax loss harvesting. It’s a good strategy when investments in a taxable account decline, but you want to avoid some traps.

Tax loss harvesting is simply selling investments in taxable accounts that have paper losses so the loss becomes tax deductible.

On your tax return, capital losses first offset any capital gains you have for the year. Each dollar of taxable loss you recognize allows you to recognize a dollar of capital gains tax free.

If capital losses for the year exceed capital gains, up to $3,000 of excess losses can be deducted against the other income on your tax return. When capital losses for the year exceed capital gains plus the $3,000 deduction, the excess losses can be carried forward to future years to be used in the same way.

Selling a losing investment can shelter other gains or types of income from income taxes and frees up the capital to be invested in something else.

Of course, you probably purchased the investment because you expected it to appreciate. If you still like the investment’s longer term prospects, you can buy it back after selling it. But you have to avoid the wash sale rule.

The wash sale rule says you have to wait more than 30 days (not 30 days—more than 30 days) to repurchase the investment or a substantially identical one. If you don’t wait long enough, the loss isn’t deductible. It’s added to the basis of the new investment and effectively the deduction is delayed until that investment is sold.

The wash sale rule also applies if you bought the substantially identical investment 30 days or less before you sold the losing investment.

So, the first rule is to avoid buying a substantially identical investment within 30 days of selling the investment.

You can buy an investment that isn’t substantially identical within 30 days of the sale. For example, you can sell one tech stock and purchase a different tech stock, even one in the same sector. Or sell a biotech stock and buy shares in a biotech ETF.

Another action you can’t take is to buy a substantially identical investment in an IRA or 401(k). The IRS ruled some years ago that the wash sale rule is violated when an individual investor sells an investment in a taxable account and within 30 days buys the same investment in an IRA or 401(k). It’s one case when the IRA isn’t treated as a separate taxpayer.

Here’s a related point. When you have a losing investment in an IRA, you won’t be able to deduct the loss on your individual tax return. A loss in an IRA is deductible only in the rare case when you fully distribute all your IRAs of the same type (traditional or Roth), and the proceeds are less than your aggregate cost basis in the IRAs.