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So should he just get a quarterly form and mail the IRS a check? Or will he not get a penalty since all previous years resulted in a refund?

One exception to the underpayment penalty is having withholding that is at least 100% (110% for higher incomes) of your prior year tax. If he meets that exception, he can pay an unlimited amount of taxes on April 15 with no penalty worries.

If he doesn't meet that exception, then estimated tax payments are in order. And depending on the timing of his gains, it may be too late to make an estimated tax payment and avoid a penalty, although the sooner the estimated tax payment is made, the smaller the penalty will be.

And it's not a terribly large penalty - it's calculated like interest from the date the estimated tax payment should have been made to the date it was actually paid. I'm pretty sure the current "interest" rate for the underpayment is 3%. I've got a few clients who are choosing to pay this penalty, as it's the cheapest short-term money they can borrow at the moment.

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