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Level 5
posted Apr 9, 2025 2:19:52 PM

What is the best way to prevent underpayment penalty when I sell lots of stock?

If I sell stock and have a large gain ($80,000 of gain) when my total income is normally around $100K, how do I prevent underpayment penalties?

 

I  have withholdings on my $50K pension but would have to ratchet them up a lot to cover this kind of gain. Can I just take 15% of the gain and pay that in estimated taxes the same quarter that I sold the stock?

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1 Best answer
Expert Alumni
Apr 9, 2025 2:22:10 PM

Yes that is exactly what the IRS wants. The IRS expects to be paid the same quarter you make the income. You can make estimated payments online at Payments.

1 Replies
Expert Alumni
Apr 9, 2025 2:22:10 PM

Yes that is exactly what the IRS wants. The IRS expects to be paid the same quarter you make the income. You can make estimated payments online at Payments.