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My employers gives me stock compensation every month. There is no day in the year I can sell my losing lots of stock without triggering the wash sale rule.

Can I sell winnings and losing lots of stocks in the same transaction to offset (but not eliminate completely) the gains of that transaction? Is that a wash sale as well?

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  • What country's tax laws are you interested in? Please add a country tag. Oct 18, 2022 at 16:19

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Yes, you seems to be "stuck" in a wash sale cycle, but all that means is that the tax benefit is deferred until you ultimately close out your position. The loss is just shifted to the cost basis of the most recent purchase. The loss is not "gone" forever.

However, the purpose of the wash sale rule is to prevent tax loss harvesting by deferring tax losses until your position is closed, but that does not seem to be your intent. I would talk with a tax attorney that deals with wash sale rules and see if there are precedents that would indicate that regularly acquired lots that prevent any 30-day window would be exempt.

But in the end, all you're doing is deferring the loss; you'll be able to claim it eventually.

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