Will Selling a stock at a loss and then selling a CSP trigger a wash sale?

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Selling shares at a loss, will selling a cash secured put of that stock out of the money that expires 30 days away trigger a wash rule?

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If the put is deep in the money then yes, it’ll be considered a wash sale. However, the tax code hasn’t defined how much in the money is considered deep. You should use extreme caution when using such techniques.

Another thing to look out for when using this technique is - what happens if the buyer of this put exercises it, and you are assigned that exercise, but it is earlier than 30 days? It’s rare, but it does happen sometimes in the USA (that people exercise puts before expiration day). It cannot happen in Europe because options there are only exercisable on the date of expiry.

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