Do I have to pay penalties if I sell stock and wait to pay the taxes later?

Dear OK: Depends on the amount. See IRS Topic 306 for details about underpayment penalties.

This advice was prepared based on our understanding of the tax law in effect at the time it was written as it applies to the facts that you provided. Click on my profile to read more. Errol Quinn Enrolled Agent Master Tax Advisor

It depends on the amount. How much did you sell? do you usually have a refund comming? Do you have any other income that you're not paying tax on throughout the year (interest, dividends, other capital gains)? Do you have any capital losses or self employment loss to offset it?

You will owe an additional penalty if your balance due come tax time next year is more than $1,000 or 10% of your AGI, which ever is greater. If you're worried about it what you could do is go into work and fill out a new W4. Have them take out some extra money each pay period to offset your other income.

You can pay whatever taxes you owe on the sale of the stock when you pay your taxes at the end of the year. The only time you might face penalties is if you have too little withheld over the year and you owe a lot at year end. You would need to pay estimated taxes quarterly if you receive a lot of income without taxes being withheld.