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How do I avoid an underpayment penalty when I do a large ROTH conversion?

How do I avoid an underpayment penalty when I do a large ROTH conversion?

 

I plan on doing a ROTH conversion of around $80K.  The goal is to put my taxable income near the top of the 24% tax bracket for single filers. That will be $197,300.

 

I have never paid estimated payments before. I receive a paycheck and get a W2 at the end of the year. 

 

Last year I converted $70K and paid a $250 penalty.

 

I'd like to avoid that this year. Does it matter when during the year I do the ROTH conversion to avoid a penalty? 

 

Thanks  

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5 Replies

How do I avoid an underpayment penalty when I do a large ROTH conversion?

You should gave tax withholding taken out on it, that will help.   Or send in an estimated payment.

If Turbo Tax calculates a penalty on 1040 line 38…..You might be able to eliminate it or at least reduce it.  You can go to Federal Taxes tab or Personal tab, under Other Tax Situations and select Start by the Underpayment Penalties. You will answer a series of questions that may reduce or eliminate the penalty. Or you can elect to have the IRS figure the penalty for you.  It's form 2210.

 

It's under

Federal or Personal (for Home & Business Desktop)

Other Tax Situations

Additional Tax Payments

Underpayment Penalties - Click the Start or update button

 

How do I avoid an underpayment penalty when I do a large ROTH conversion?

Check your safe harbor calc - see Form 2210 line 1-9, to avoid penalty you need to have paid during the year via withholding or "timely" estimated taxes, the smaller of 100% of your 2024 tax (110% if AGI > 150k of 75 if filing MFS), or 90% of your 2025 tax.

 

Withholding is always considered timely regardless of when it happens, but given you did a large Roth last year also it sounds like W2 withholding alone will not meet the safe harbor.

 

For a large Q4 Roth conversion, you would likely need to make a Q4 estimated tax payment in January to meet the safe harbor amount (which may not be the full 24% tax due on the conversion - the rest is due by next April), and then when you file your return will need to adopt the Annualized Income method on Form 2210.  Without that method by default, IRS (and TT penalty calc) will assume this distribution happened evenly thru the year and you were therefore underpaid in Q1-3 etc which is why you got the large penalty.  For the AI method you will need to calculate your AGI, withholding, Qualified Divs, LTCG etc by quarter (not even quarters tho  - 3/31, 5/31, 8/31, 12/31) and that will show the uneven income in those buckets and that the estimated tax in Q4 was not late.  It may not entirely eliminate the penalty if other things didn't quite line up but should significantly reduce it.  When you do your 2025 filing you would trigger this process under Other Tax Situations / Underpayment Penalty section and check the outcome on your 1040 Line 38.  But beware these quarterly calculations you need to do yourself and input into Turbo.  You would need to do a similar process for your state taxes also if applicable.

 

There is an alternative approach where you can do withholding on the Roth conversion which will reduce the amount deposited into your Roth (e.g. 80k comes out of your Trad IRA, 20k withheld, 60k goes into the Roth), which is taking money from your retirement accounts - but you can then send in that amount directly within 60 days to make it up.  I've not tried that method and don't know what's involved with your brokerage to process that deposit into the Roth correctly and not be coded as a contribution - perhaps @VolvoGirl can elaborate if questions on this approach.

 

Going forward if you're continuing to do these conversions annually, the easiest way is to figure your safe harbor in Q1 when you file for prior year, based on known prior year tax along with estimate of your withholding, and pay even quarterly ES payments thru the year to meet that.  You can then just do your Roth conversion whenever during the year or even in pieces, it doesn't matter.  When you do your 2025 filing, the ES vouchers for 2026 generated by TurboTax will do this calculation by default, using 100/110% of your 2025 tax as the safe harbor and assuming your 2026 withholding is the same as 2025, and the difference between the two is your estimated tax and divide by 4 for the quarterly amount.  You can update these assumptions under Other Tax Situations / Form W4 and Estimated Tax section and see if you can optimize the ES payments further.

 

Finally try to avoid sending checks and using 1040-ES vouchers, pay ES directly electronically at irs.gov (I do the same with final tax due - tell Turbo you're sending a check rather than give direct debit details, and then pay directly at irs.gov when you want, it's easier to control timing especially for large amounts due - IRS will hit your account by next business day).

 

Check into the details of the safe harbor, penalty calls and AI method on Form 2210 for more details.

How do I avoid an underpayment penalty when I do a large ROTH conversion?

" Does it matter when during the year I do the ROTH conversion"

 

It matters when you make the Estimated Tax quarterly payments.

If your quarterly withholding and estimates for 2025 are at least 100% / 4 = 25% ( 110% / 4 for certain high income taxpayers) of your 2024 tax, there will be no penalty on your 2025 tax return, regardless of any jump in income.
you are protected from a sudden capital gain or spike in income at year end.
you know your prior year's tax when you file by April 15, which is also the first estimated tax payment due date.

----

OR

If you can arrange to meet the "Required Annual Payment"

 entirely through withholding ,  the timing does not matter. ES payments are not needed. There will be no penalty.

This is the default basic rule.

Otherwise, see Form 2210 Schedule AI for how to reduce your penalty.

 

@Kipmc7 

How do I avoid an underpayment penalty when I do a large ROTH conversion?

@baldietax  Thank you for a very thorough answer.

 

I believe you mean that to avoid a penalty, you must pay at least the smaller of :

1) 100% of your 2024 tax (110% if AGI > 150k or 75 if filing MFS), or

2) 90% of your 2025 tax

 

Correct?

 

Re the AI method. you said :

 

For the AI method you will need to calculate your AGI, withholding, Qualified Divs, LTCG etc by quarter (not even quarters tho  - 3/31, 5/31, 8/31, 12/31) and that will show the uneven income in those buckets and that the estimated tax in Q4 was not late.

 

This seems very complex. Is there guidance on how to do that?

 

Thank you

How do I avoid an underpayment penalty when I do a large ROTH conversion?

yes on the safe harbor recap I see my typo there thanks for clarifying.  there're more guidance on this topic here

https://turbotax.intuit.com/tax-tips/irs-tax-forms/what-is-form-2210/L2z0haVWb

 

Yes 2210 AI can be a pain to do, depending how complex your situation is and whether it's worthwhile depends on how much penalty you are trying to eliminate.  You're doing mini tax returns for each quarter, and have to self-calculate the AGI i.e. replicate lines 1-11 on Form 1040, splitting up your income and any line 10 adjustments etc.  Turbotax won't guide much it just asks for those inputs then does the rest of the form 2210 mechanics - the annualization and tax calcs, and needs breakdown of LTCG/Qualdivs and withholding to do that.  There's probably other 3rd party advice on it if you do some searches and also go thru the Form 2210 instructions.

 

There's one other option which still involves some penalty but I'll put it out there, which is to adopt quarterly ES payments late, and quickly catch up your Q1-3 ES installments now to stop the penalty accruing, then pay Q4 in January.  At this point (mid Oct) your Q1 installment is about 6 months late, Q2 is about 4 months late, Q3 is about 1 month late, with an annual penalty rate for 2025 of 7%.  So for example if your total ES due was 10k for a quarterly ES of 2.5k, the penalty at this point if you catch it up should be (roughly) $2500 * (6+4+1)/12 * 7% = $160.

 

If you do not pay any ES at all then by default and without the AI method, for the same example, your final penalty by mid April would be roughly 2500 * (12+10+7+3)/12 * 7% = $467.

 

(if my penalty math is correct)

 

Beware also the $250 penalty last year may have been based on a lower safe harbor based on your 2023 tax which won't apply this year if you've being doing sizable Roth conversions since 2024, and the 'default' penalty if you do nothing could be much higher than last year.

 

One tip if you are using desktop TT, in forms mode you don't see Form 2210 by default, but if you double-click line 38 on Form 1040 then double-click the same line in the worksheet, TT will then show the 2210 form and penalty calculation.

 

Hope that helps.

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