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Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

I am planning a large Roth conversion before the end of the year. I think this will trigger an underpayment penalty for me. I should have been paying quarterly payments because the amount to get in the safe harbor would have been very small. If the penalty is based on what I would have need to pay to be in the safe harbor, it won't be very significant. If the penalty is based on the actual tax I will owe for this year, it will be much more significant. I'm trying to determine if the penalty will be large enough that it should affect how large of a Roth conversion I should do. I hope this makes sense! Thank you so much in advance for your input!!
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8 Replies

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

The income from the conversion is assumed to be spread over the 4 quarters. 

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

Right, so I'm trying to figure out either how to minimize a penalty or avoid it completely.  If I do this Roth conversion now, but haven't been paying estimated quarterly taxes, I'm trying to figure out (1) how large will the penalty be and (2) if it's large, if there are ways I can minimize it or eliminate it completely.

 

On (1), if the penalty is based on what I would have needed to pay quarterly to be in the 100% of previous year's tax safe harbor, it would be very small because I had a very small tax liability last year.  If instead it's based on the say $10k I will owe this year in tax, my understanding is I could use form 2210 (schedule AI?) to make it clear that this income from the Roth conversion (which will be the vast majority of my income for the year) happened in Q4 and that is when I made a tax payment to cover that tax liability from the Roth conversion income.

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

Pay an amount of estimated tax now to cover your expected tax liability and you will be fine. 

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

You are correct that if you only make an estimated payment, you can be subject to underpayment penalties for the previous quarters.  I believe the penalty is based on the actual tax owed, not including a fudge factor for what the minimum correct estimated payment would have been. 

 

To minimize the tax owed, you can do one of two things.

 

1. Pay the estimated tax in the quarter that you do the conversion, and then include form 2210 schedule AI with your return.  This is the annualized income method of calculating the penalty, and it will show the IRS that your income was uneven and your payments in each quarter were correct for your income in each quarter.  (Turbotax may not automatically trigger the penalty interview, but you can manually open the interview if Turbotax does not automatically run it for you.)

 

2. Have the tax withheld from the conversion.  Withholding is assumed to be spread out over the whole year, just like income, so a penalty never evens comes up.  For example, if you want to convert $10,000, have them withhold 22% and send you a check for $7800.  You then send a check to the new Roth for $10,000 (by making up the difference from the funds you would have used to pay the estimated taxes).  This is an indirect rollover, that you can only do once per year.  The withholding will appear on your 1099-R.

 

Or, you can inquire of the receiving custodian if they will assist you in doing a rollover with withholding.  For example, if you tell them "I want to roll over $10,000 but have withholding, can I have my plan send you $7800 and then I make an electronic payment of $2200 and we call it a rollover of $10,000?"  I'm not sure this is possible but you can ask.  Having withholding eliminates the need for a penalty calculation.  

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

there are two basic rules to avoid underpayment of estimated taxes

to avoid penalties for underpayment of estimated taxes:

1) withholding and timely estimated tax payments must equal 90% of your current year's tax

or

2) withholding and timely estimated tax payments must equal 100% of the prior year's tax. this jumps to 110% of the prior year's tax if your prior year's adjusted gross income (line 11 of the 1040) is more than $150,000

$75,000 if married filing separate) 

 

your goal is the lower of 1 or 2. since it seems you will have a significantly larger tax bill in 2024 than 2023, your goal would be the second option. 

 

 

under either option, withholding is assumed to occur evenly throughout the year but if you're completing form 2210 you can use actual withholding for each period. estimates are counted for the period if made on or before their due date

dmertz
Level 15

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

With a large Roth conversion, I assume that, if nothing is withheld for taxes, the total underpayment for the year will be more than $1,000 and more than 10% of the tax owed.  If that's the case, the penalty will be based on the quarterly underpayment of the amount needed to meet the safe harbor based on your 2023 tax liability.

 

Opus 17's suggestion #2 is probably the easiest way to avoid any underpayment penalty.  Just be aware that the amount withheld for taxes will be uninvested until the check to complete the entire conversion is deposited into the Roth IRA.

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?

Thank you all for the input, I greatly appreciate it!  One thing I know I'm going to do going forward is pay quarterly estimated taxes to make sure I'm in the safe harbor, so I don't need to think more about it.

Is the underpayment penalty calculated on actual tax owed or on the amount I would have needed to pay quarterly to be in the safe harbor?


@jdbollinger wrote:

Thank you all for the input, I greatly appreciate it!  One thing I know I'm going to do going forward is pay quarterly estimated taxes to make sure I'm in the safe harbor, so I don't need to think more about it.


One very simply option would be to make the conversion in the first quarter of the year instead of the last.  That way, you can spread out the estimated payment over the whole year, and benefit from having that money in the mean time (maybe in an interest bearing account) and still be in compliance with the penalty rules.   The IRS wants to see the estimated payment spread out over the whole year if the conversion is done late, but they also allow the payments to be spread out over the whole year if the conversion is done early. 

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