As a certified public accountant, the most common question I hear in the spring is, “How much do I actually have to pay the IRS right now?” In a perfect world, the IRS wants 90% of your total tax liability paid “ratably” (equally) throughout the year.
The problem? Most successful people don’t have perfectly predictable incomes. Whether it’s a year-end bonus, a business windfall, or a volatile stock market, hitting that 90% target is like trying to pin a tail on a moving donkey. If you miss, you face underpayment penalties.
Fortunately, the tax code provides several “safe harbors” and strategic maneuvers. Here are five options for handling your 2026 tax obligations.
1. The December miracle: late-year withholding
One of the most powerful “hacks” in the tax code involves the definition of withholding. Unlike estimated tax payments (which are credited on the day you mail the check), withholding is treated as being paid equally throughout the entire year, regardless of when it actually happens.
The Strategy: If you realize in November that you’re underpaid, you can’t simply mail a massive, estimated tax payment to erase previous quarterly shortfalls—the penalty for the early quarters is already locked in. However, you can ramp up your withholding on your final December paychecks or take a “tax only” IRA distribution with 100% federal withholding.
The Benefit: Because the IRS treats that December withholding as if it were paid throughout the year, it can retroactively eliminate underpayment penalties for the entire year.
2. The ‘Rearview Mirror’ safe harbor
If you want to be “bulletproof” against penalties regardless of how much you earn this year, look at last year’s tax return. This is the most common strategy for high-income earners.
The Strategy: Pay in an amount based on your 2025 total tax. If your adjusted gross income is $150,000 or less, pay 100% of last year’s tax. If your AGI is over $150,000, you must pay 110% of last year’s tax.
The Benefit: Even if you sell a business for a $10 million profit in 2026, you will not owe any penalties in April 2027 as long as you hit that 110% of the 2025 benchmark through equal quarterly installments.
3. The ‘Pay-As-You-Go’ (annualized) method
If your income is seasonal—for example, you’re a consultant who gets paid in the fourth quarter, or you have a concentrated stock position you plan to sell in the summer—paying equal amounts in April and June feels unfair and creates a cash flow crunch.
The Strategy: Use the annualized income installment method. This requires performing a “mini tax return” calculation every quarter based on what you have actually earned to date.
The Benefit: It allows you to pay very little in the early quarters when income is low and only “catch up” when the big checks actually arrive. It’s more paperwork, but it keeps your cash in your pocket longer.
4. The ‘Strategic Penalty’ approach
Sometimes, the most mathematical move is simply not to pay until April. The IRS underpayment penalty isn’t a criminal fine; it’s essentially an interest charge for using the government’s money.
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The Strategy: If you have an investment opportunity or a high-yield environment where your money can earn more than the IRS interest rate, you might choose to underpay intentionally.
The Benefit: As of early 2026, the federal underpayment rate is hovering around 7%. If you are confident you can net a significantly higher return elsewhere, or if you simply value the liquidity, paying the interest in April might be a calculated business decision.
5. The hybrid strategy: minimums plus catch-up
Many savvy investors combine these methods. They set their quarterly payments to exactly meet the 110% safe harbor (strategy No. 2) to guarantee no penalties, and then they hold the “excess” tax they know they will eventually owe in a high-yield savings account or short-term Treasurys until April 15.
The Benefit: You get the security of no penalties, the simplicity of equal payments, and the interest bonus on the remaining balance.
You have options
Whether you prefer the set-it-and-forget-it 110% safe harbor, the surgical precision of annualizing your income, or the late-year withholding bailout, you don’t have to be a victim of an unpredictable income year. And remember that your state might have different rules.
This article was provided to The Associated Press by Morningstar. For more personal finance content, go to https://www.morningstar.com/personal-finance.
Sheryl Rowling, CPA, is an editorial director, financial adviser for Morningstar.
Related Links
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