How to make it work for YOU re: Estimated Taxes

Home Fairmark Forum Taxation of Investments How to make it work for YOU re: Estimated Taxes


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    Let’s say you sell stock at a large profit near the beginning of the year. Then, you make far less gain for the next of the year. I don’t want to pay 110% of what would be a huge amount based on last year’s earnings.

    There must be a way to game this rotten system. Kay mentioned filling out the 2210 forms as a nightmare. There’s no reason we would have to jump through spiked hoops for the rigged IRS.

    Kaye, do you have any other suggestions? What about putting your big gains on an Estimated Tax Worksheet (I believe that is different than the 2210) in your forth quarter, so you will not have gained much until the last quarter, and the formulas you use bring down the percentage of tax in the last two quarters. Throw the 2210 in the garbage, and use the Estimated Tax Worksheet. I doubt very much that the IRS computers match your 1099B gain dates with the dates you put down on that form.

    Kaye Thomas

    Note that you aren’t required to use the previous year’s income if doing so produces higher estimates than you would pay based on the current year’s income. Note also that although the general requirement is for estimated tax to be paid quarterly, you have a choice as to whether to make those payments based on income in each quarter or based on the entire year’s income. The “rotten system” actually works in your favor, allowing you to pay the tax owed on a large hit of income in the first quarter over the entire year, but allowing you to postpone payments if income is bunched in the last quarter.

    There’s another way the system works in your favor if you have (or can contrive to have) income subject to withholding. Tax paid through withholding is treated as if paid over the course of the year, even if it was entirely paid in late December. Therefore, you can avoid an underpayment penalty by arranging with an employer to withhold extra dollars late in the year, or take money from an IRA late in the year to cover the tax bill, choosing to have the amount needed to cover it withheld and paid to the IRS rather than paid out to you. Note that the IRS withdrawal, including the amount withheld, would be taxable income, and potentially subject to penalty if you haven’t reached age 59½.

    Not everyone has these options available, but here’s another point. The penalty for underpaying estimated tax is really just simple interest on the amount by which you underpaid. The interest rate is based on market rates, which are at historic lows. No one is going to be devastated by incurring this penalty. The greater concern in failing to make estimated tax payments is the risk of failing to keep enough money aside to meet the tax liability when April 15 rolls around, and more meaningful penalties come into play.

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