Q. A large portion of my portfolio is invested in Internet stocks and with the recent market downturn, I’ve accumulated some substantial losses on certain stocks. Although I think these stocks will eventually turn around, I’d love to use some of those losses to offset gains from other stocks I’d like to sell. From a tax standpoint, can I sell stock at a loss and then turn around and immediately buy it back? A. If only it were that simple. The transaction you are proposing is considered a “wash sale” in the eyes of the IRS. A wash sale is the sale of a security (e.g., stock or bond) at a loss where the taxpayer turns around and buys back substantially the same security within 30 days. With the wash sale rules, the IRS seeks to eliminate the ability to deduct current losses on these types of transactions, and instead allows a basis adjustment to the new security purchased, in effect deferring the recognition of the earlier loss.

Example: You sell 1,000 shares of Dotcom Co. stock at a loss of $2,000. Next week, you buy another 1,000 shares of the same company’s stock for $5,000. Instead of allowing the deduction of the $2,000 on your return, the wash sale rules say you must instead adjust the basis of your newest purchase to $7,000. When you go to sell the stock later at say $10,000, instead of having a $5,000 gain ($10,000 sales price minus $5,000 purchase price), your gain would only be $3,000 ($10,000 sales price minus $7,000 adjusted basis).

So how do you avoid the wash sale rules? Keep good track of the purchase and sale dates of your securities. If you do feel the need to reinvest in a similar investment vehicle, make sure that some element of the new security is different enough to avoid the “substantially similar” rule (e.g., if you sell a stock mutual fund, you can purchase another type of stock mutual fund.) As always, please contact the office if you need further clarification of the wash sale rules.