Using IRAs to Pay Income Taxes In Retirement

It’s the fourth quarter. Now is a great time to check and see if you are on pace to have enough federal and state income tax paid in for 2024.

It happens: people get to the end of the year and see they are severely underwithheld. What do you do in such a situation?

This post explores using IRAs to pay income taxes and explores a novel approach: using a 72(t) payment plan to pay income taxes. 

Income Tax Withholding Requirements

Before we discuss curative tactics, let’s briefly review the requirements. In order to avoid an underpayment penalty for 2024, on must pay in, either through withholding (could be W-2 or 1099-R, we’ll come back to that) or quarterly estimated tax payments, either (or both) 90% of the current year’s tax liability or 100% of the prior year’s tax liability. These are the two so-called “safe harbors.” For those with an adjusted gross income of more than $150,000 in the prior year, that 100% safe harbor increases to 110%.

The 100%/110% safe harbor protects the late-in year lottery winner (among others). As long as he or she has withholding or estimated tax payments that meet 100% or 110% (as applicable) safe harbor, he or she can have millions or billions of dollars in income, meet the safe harbor requirements, avoid the underpayment penalty and pay most of the 2024 tax by April 15, 2025. 

Estimated tax payments are great, but they require early in the year action not possible in the fourth quarter. To meet the safe harbor, generally one quarter of the total amount due under the safe harbor must be paid by April 15th, June 15th, September 15th, and the following January 15th. That’s great, but for those who didn’t make the first three payments going into the fourth quarter, estimated tax payments may not be all that helpful at this point. 

Most states with an income tax have rules that mirror the federal income tax withholding rules, but some states have differences. 

The Retiree’s Secret Weapon for Estimated Tax Payments

Retirees have a secret weapon for making income tax payments, particularly late in the year. IRAs! 

People miss paying taxes during the year. It happens for a variety of reasons. If I were a retiree and I found myself underpaid for either (or both) federal and state income taxes purposes in the fourth quarter, the first place I would look to make an estimated tax payment would be a traditional IRA. 

Why?

Because income tax withheld from a traditional IRA is deemed paid equally to the IRS throughout the year regardless of when the withholding occurs. 

IRA owners can initiate a distribution from their traditional IRA and direct that most of it be directed to the IRS and/or the state taxing authority. That withholding is treated as if it is paid equally throughout the year regardless of whether it occurs on January 5th or December 21st.

That’s pretty good! A late in the year IRA distribution withheld to the IRS can meet either (or both) the 90% safe harbor and/or the 100%/110% safe harbor. 

The downside is that it creates taxable income. In many cases, it turns out retirees are rather lightly taxed. As long as the retiree had a relatively low income tax burden either last year or this year, the taxable withdrawal won’t be a large number, because the applicable required safe harbor withholding will be modest. Thus, the tax hit on the mostly withheld distribution should be rather modest. 

Another advantage of using a traditional IRA to pay income taxes is RMD mitigation. While I believe the concerns around RMDs are wildly overstated, RMD mitigation is a perfectly valid financial planning objective and a good outcome. 

Using an IRA to Pay Income Taxes Under Age 59 ½

You may now be thinking “Sean, that’s a great idea for those over age 59 ½. But what if I’m under age 59 ½? Won’t I be subject to the 10% early withdrawal penalty on the amount I fork over to the IRS?”

That’s an excellent thought! Fortunately, the answer to your questions is “maybe.”

The IRS maintains a list of exceptions to the 10% early withdrawal penalty. Many will not be applicable to most retirees. But there are some options–let’s explore two of them: Inherited IRAs and 72(t) payment plans. 

Inherited IRAs

Beneficiaries of inherited IRAs never pay the 10% early withdrawal penalty with respect to distributions from their “inherited IRAs.” Thus, the inherited IRA is a great place to look to pay taxes from late in the year.

The only downside is the distribution to the IRS or the state taxing authority is itself taxable to the beneficiary. However, the money in the inherited IRA has to come out eventually (usually under the 10 year rule at a minimum), so why not whittle the traditional IRA down by using it to pay income taxes and avoid an underpayment penalty?

72(t) Payment Plan to Pay Income Taxes

Could someone start a 72(t) payment plan to pay required income taxes? Absolutely, in my opinion. It might even be a good idea!

72(t) Payment to Pay Income Taxes Example

Homer and Marge both turned age 56 in the year 2024. They retired early in 2023 and thus had some W-2 income and some investment income in 2023. They had approximately $120K of adjusted gross income in 2023 and thus paid approximately $8,800 of federal income taxes in 2023 (see Form 1040 line 24 less most tax credits — see the comment below) and $2,000 of California income taxes in 2023. 

In 2024 they have ordinary income below the standard deduction and taxable income below the top of the 12% federal income tax bracket. Thus, they owe no federal income tax and a very small amount of California income tax for 2024. They’ve made no estimated tax payments.

In August 2024 they decided to sell their Bay Area home worth $2M to move to a more rural part of California. The sale closed in October 2024 and they had a $500,000 basis in the home. Qualifying for the $500K exclusion, this triggers a $1M taxable long term capital gain to Homer and Marge in 2024. D’oh! 

Very, very roughly, the capital gain creates approximately $175K of federal income tax, $30K of federal net investment income tax, and $100K of California income tax. Note also that the proceeds from the home sale are likely to cause some taxable income in December 2024, but let’s just use the above three tax numbers for illustrative purposes only. 

One of their other assets is a $2M traditional IRA. They have no inherited retirement accounts but they do have some taxable brokerage accounts. To my mind, there are four main ways Homer and Marge can avoid an underpayment penalty.

Option 1: Q4 Estimated Tax Payments

Homer and Marge could make substantial fourth quarter estimated tax payments out of their taxable brokerage accounts by January 15, 2025. They would owe 90% their entire 2024 tax liability at that time and would need to use annualization on the Form 2210 to avoid an underpayment penalty. 

Compared to the other three methods described below, this costs them 3 months of interest on about $275K. In today’s interest rate environment, that is about $2,700 of interest in an online FDIC insured savings account.

Option 2: IRA Regular Distribution

Homer and Marge could, no later than December 31st, trigger a distribution from one of their traditional IRAs, say for $11,100. They could direct the institution to send $8,880 (80%) to the IRS, $2,109 (19%) to the California Franchise Tax Board, and $111 (1%) to themselves (the intuition will likely require they take at least 1% of the distribution). This creates $11,100 more taxable income (taxed at a low federal rate due to income stacking).

The advantage is this qualifies for the safe harbor, meaning Homer and Marge don’t have to pay most of their 2024 income tax until April 15, 2024. The downside to this is it triggers a 10% early withdrawal penalty ($1,110) payable to the IRS and a 2.5% early withdrawal penalty ($278) payable to California. 

Option 3: IRA Regular Distribution and Rollover

This option is the IRA Regular Distribution option plus refunding the $11,100 traditional IRA distribution to the traditional IRA from their taxable accounts within 60 days. This has all the same advantages as the IRA Regular Distribution option plus it reduces 2024 taxable income by $11,100 and avoids the early withdrawal penalties.

Gold, right? My view: I tend to disfavor this tactic. Why? Americans are limited to one 60 day rollover from an IRA to an IRA every 12 months. My personal opinion is that pre-age 59 ½ retirees are usually better served to keep that option on the table. You never know when a significant sum will pop out of a traditional IRA. It will be good to have the option to put that money back into the traditional IRA. If Homer and Marge do the $11,100 IRA Regular Distribution and Rollover, they are locked out from the ability to do a 60 day IRA to IRA rollover for the next 12 months.

Option 4: 72(t) Payment Plan

This option is simply the IRA Regular Distribution option as part of a 72(t) payment plan. The advantage of adding the 72(t) payment plan is avoiding the 10% early withdrawal penalty (federal) and the 2.5% early withdrawal penalty (California). 

Here’s how it works. Before making the $11,100 IRA withdrawal, Homer and Marge do a 72(t) distribution calculation and have their financial institution set up a $172,116.10 72(t) IRA. Here is the 72(t) fixed amortization calculation:

ItemAmountSource
Interest Rate5.00%Notice 2022-6
Single Life Expectancy Years at Age 5630.6IRS Single Life Table
Account Balance$172,116.10
Annual Payment$11,100.00

Homer and Marge then take the distribution from the 72(t) IRA prior to the end of 2024, directing 80% to the IRS and 19% to the Franchise Tax Board.

You say, but wait a minute, now they have $11,100 they have to take annually for each of the following four years. I say, well, okay, they have $2M in tax deferred accounts, why not take some of that without a penalty (perhaps as a form of the “Hidden Roth IRA”) and whittle down future RMDs a bit? 

That said, Homer and Marge can drastically reduce the annual 72(t) payment if they want with a one-time change to the RMD method. Assuming the 72(t) balance on December 31, 2024 is $164,000, here’s what the 2025 taxable RMD from the 72(t) could look like:

ItemAmountSource
Account Balance$164,000
Single Life Expectancy Years at Age 5741.6Notice 2022-6 Uniform Life Table
2025 Payment$3,942.31

One would hardly expect that $4,000 of taxable income would derail Homer and Marge’s tax planning in retirement. Further, they can direct most of that $4,000 to the IRS and Franchise Tax Board to help take care of 2025 tax liabilities, if any. 

Conclusion

For those under age 59 ½, a 72(t) payment plan might be the answer to an underpayment of estimated taxes problem. It is a bit of an “out of the box” solution, but it has several advantages. It allows some taxpayers to delay paying significant amounts of tax until April 15th of the following year by qualifying the taxpayer for the 100% of prior year tax safe harbor. Second, it avoids the 10% early withdrawal penalty. Third, it avoids the once-every-twelve-months 60 day rollover rule. Lastly, a 72(t) payment plan is rather flexible and the required taxable distribution in future years can be significantly reduced by a one-time switch to the RMD method. 

The above said, the first IRA I would look to if I was under age 59 ½ and looking to pay estimated taxes is an inherited IRA. Those are never subject to the early withdrawal penalty and can always be accessed in a flexible manner. 

FI Tax Guy can be your financial planner! Find out more by visiting mullaneyfinancial.com

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This post is for entertainment and educational purposes only. It does not constitute accounting, financial, investment, legal, or tax advice. Please consult with your advisor(s) regarding your personal accounting, financial, investment, legal, and tax matters.Please also refer to the Disclaimer & Warning section found here.

8 comments

  1. When looking at the previous year’s tax liability, do you strictly look at line 24 of Form 1040, or would refundable tax credits (which get shown as “payments”) reduce this amount?

    Also, would a Roth conversion provide an opportunity to pay tax late in the year?

    Thanks for all your content

    1. Thanks for commenting.

      You make an excellent point! Most tax credits are good for lowering the “tax” for purposes of the 100%/110% safe harbor purposes. See Section 6554(f)(4) https://www.law.cornell.edu/uscode/text/26/6654#f_4 The credit for our W-2 withholding doesn’t count as a good credit for that purpose (which makes sense).

      I generally do not like having Roth conversion amounts withheld, because you’re getting less bang for your Roth conversion buck. Convert $40K to Roth but have $4K withheld — you’re only getting $36K into the Roth and the $4K that goes to the IRS can attract the 10% early withdrawal penalty. So I’d rather use a distribution and direct it to be mostly withheld.

    2. Excellent informative post, Sean. Thank you.
      Just to clarify/confirm my understanding – if a person had zero tax liability the previous tax year (2023), and did a Roth conversion in November 2024, no underpayment penalty would be assessed because the person paid 100 percent of their previous year’s tax (which was zero in this example)? No estimated or withholding payments would be necessary, even for tax amounts over 1k? Thanks.

  2. I didn’t realize you could use IRA this way, thanks! I was thinking of doing my first Roth IRA conversion this month would also lead to a big estimated tax due. If I didn’t make larger payments during the first three quarterly payments to account for this conversion, would I owe a penalty?

    1. Thanks for reading. Unfortunately, I can’t give personalized advice in the blog comments.

  3. Thanks for this post! I’m looking for both a short term loan from my IRA and catch up with substantial fed and state taxes. Looking into this option it sounds perfect. And it seems my wife can also do this from her account get the loan to 120 days.

    1. Thanks for reading. While I can’t give personalized advice on the blog, I can say in an academic sense loans are not possible from IRAs but are possible from some 401(k)s, though I tend not to like those. In theory one can take a “loan” from an IRA which is really just a 60 day rollover, but I tend to strongly disfavor that as well due to the once-every-12-months rule.

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