Tax planning and compliance for investors
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By Kaye A. Thomas
Updated June 1, 2007
The wash sale rule can apply to trades involving stock options.
Options present two different types of problems in connection with the wash sale rule. First, if you sell stock at a loss, you can turn that sale into a wash sale by trading in options. And second, losses from the options themselves can be wash sales.
If you sell stock at a loss, you'll have a wash sale (and won't be able to deduct the loss) if you buy substantially identical stock within the 61-day wash sale period consisting of the day of the sale, the 30 days before the sale and the 30 days after the sale. You'll also have a wash sale if, within the wash sale period, you enter into a contract or option to buy substantially identical stock.
Example: On March 31 you sell 100 shares of XYZ at a loss. On April 10 you buy a call option on XYZ stock. (A call option gives you the right to buy 100 shares.) The sale on March 31 is a wash sale.
It doesn't matter whether the call option is in the money. This is an automatic rule. If you buy a call option in this period, you'll have a wash sale. And that's true even if you never exercise the option and acquire the stock.
You can also turn a sale of stock into a wash sale by selling put options. This rule is not automatic. It applies only if the put option is deep in the money — and there's no precise standard as to when a put option is deep enough in the money for the rule to apply. The rule applies if it appears, at the time you sell the put option, that there is no substantial likelihood it will expire unexercised. In this circumstance, selling the put option can be roughly equivalent to buying the stock.
Example: On March 31 you sell 100 shares of XYZ at a loss. On April 10 you sell a put option giving the holder the right to sell to you 100 shares of XYZ at a price substantially higher than the current market price of the stock. The sale on March 31 is a wash sale.
As seller of a put option that's deep in the money, you participate in the upward and downward movement of the stock price, unless the price moves higher than the option price. If the option price is high enough, the chances of that happening are small, and you've simply found a different way to continue your investment in the stock.
Congress amended the wash sale rule in 1988 so that it applies directly to contracts or options to buy or sell stock or securities. That means you can have a wash sale when you close an option position at a loss, if you establish a replacement position within the wash sale period. The Treasury has yet to issue regulations under this rule, and a host of questions remain unanswered. Foremost among these is the question of when one option is substantially identical to another option.
Until the Treasury decides to issue regulations or other guidance, neither I nor anyone else can say exactly how the wash sale rule applies to losses on options. But there's a pretty good rule of thumb that should tell you when you're safe and when you're on thin ice. If the positions you acquired within the wash sale period permit you to participate in the same up and down market swings as the position that produced the loss, there's a chance the IRS will say you have a wash sale. If that's not the case, you should be safe.
Suppose you've sold a call option at a loss. Buying another call option on the same stock within the wash sale period may be viewed as a wash sale even if the new call option has a different expiration or a different strike price. The IRS might assert that you have a wash sale if you buy XYZ stock, especially if the call was in the money when you sold it. Similarly, you could also have a wash sale if you write a deep-in-the-money put option during the wash sale period.
By contrast, you shouldn't have a wash sale if you sell a call option at a loss and also write a put option that's at the money or out of the money. The long call option and the short put option are both bullish positions, but the short put option doesn't let you participate in the upside.
These remarks are simply my interpretation, and won't necessarily reflect the interpretation of the IRS or the Treasury. What's more, other tax pros may have a different take on this question. Unfortunately, there's no sign that official guidance on these issues will be forthcoming in the near future.
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