Question

Do I have to report a stock loss? A -$37 loss is making me pay $129 just for a schedule 'D' form.

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Yes. You'll have to file a Schedule D form if you realized any capital gains or losses from your investments in taxable accounts.

If you don't report a loss on the sale of a Stock, the IRS will assume the proceeds from said sale to be all profit - assess tax on a false gain.

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