Guides

Withholding and the Estimated Tax Penalty: Box D Timing

Checked October 17, 2026 · Educational summary

General information, not tax, legal or financial advice. We are not the IRS. Check IRS.gov or a qualified tax professional. Sources read on October 17, 2026. Dates for 2027 and later are expected. Examples use made-up numbers. This page contains no affiliate links.

For the estimated tax penalty, the Instructions for Form 2210 (2025) say you are considered to have paid one-fourth of your federal withholding on each payment due date unless you can show otherwise. If you instead treat withholding as paid on the dates it was actually withheld, you must check box D in Part II and attach Form 2210 to your return. This can matter when most of your withholding came late in the year, for example from a year-end bonus (our example; the instructions do not mention IRA withdrawals).

The rule (2025 instructions)

• Withheld federal income tax counts as paid in four equal parts on the four due dates.
• Taking actual dates requires box D and Form 2210 attached.
• You must include all estimated payments you made for each period; if you mail them, the U.S. postmark date counts as the payment date.

How overpayments and January payments are treated

• An overpayment from the prior-year return that you applied to this year's estimated tax is treated as paid on April 15 if the prior return was fully paid before April 15.
• If the overpayment arose from a payment made later, it counts from the date of that payment.
• For 2025, the instructions say that if you filed your return and paid the tax due by January 31, 2026, you would not owe a penalty for the January 15, 2026 payment. For 2026 the matching date is expected to be January 31, 2027 (see the January guide).

Ordering of payments

Your payments are applied first to any earlier underpayment, even if you designate them for a later period. The IRS example: a $500 underpayment remained after April 15; a $1,200 payment on June 10 for the June 15 installment first covers the $500, so the April penalty runs to June 10 and $700 goes to the June installment.

Made-up illustration

You have no withholding until a $12,000 withholding on a December bonus. By default the IRS treats a quarter of it as paid on each due date. Choosing actual dates (box D) could change the penalty, but requires you to file and attach Form 2210. Whether that helps depends on your numbers; we do not compute it.

On the form, box D reads: your penalty is lower when figured by treating the federal income tax withheld as paid on the dates it was actually withheld; you must figure your penalty and file Form 2210. The IRS has posted a draft of the 2026 Form 2210, but the 2026 instructions are not yet published.

Related

Raise W-4 withholding instead of quarterly payments · Form 2210: boxes and waivers · Underpayment penalty · Retirees and withholding

FAQ

Can I change withholding late in the year?

That is done with a new Form W-4 given to your employer; we did not read details of timing here.

Does withholding even out the penalty automatically?

Only under the default evenly-spread rule; box D is an election.

What we could not verify