Estimated Payments/Timing

1. Yes, you can do this. However, it is my understanding and belief that if the $11K tax payment enables you to reach any of the several safe harbors, you would not be required to file Form 2210...

You are never required to fill out form 2210. The IRS is happy to calculate the penalty for you by assuming that your income was spread equally through the year. :(

However, Cobra is correct that you can still owe a penalty for underpayment even if you reach the safe harbor. See https://www.irs.gov/instructions/i2210

In general, you may owe the penalty for 2020 if the total of your withholding and timely estimated tax payments didn't equal at least the smaller of:

90% of your 2020 tax, or
100% of your 2019 tax. Your 2019 tax return must cover a 12-month period.

The key word there is "timely". Making the full safe-harbor payment as a Q4 estimate won't negate the penalty.

I think the IRS doesn't actually issue penalties in most cases though. I suspect that they really only do the math if they're looking at your return for some other reason or if you filed late and the balance due was a large percentage of the total tax. We get a lot of folks at our Tax-Aide site whose returns get the "might have a penalty" message, and even when I know they actually should owe a penalty, they usually come back the next year and say they never heard anything from the IRS.
 
...
3. Do the $100K Roth conversion. Withhold $22K during the conversion transaction. Net conversion amount is $78K. To complete the conversion, replace the $22K in the Roth within 60 days from non-retirement funds. This achieves all the same benefits as #2. Also, it is not subject to the once-per-year limitation since it is a conversion, not a rollover. However, if done late in the year, with the $22K replaced in Jan of the following year, the entire $100K is taxable in the first year, while the 5-year holding period is based on the year of contribution, which might require some careful record-keeping.

... In part, because I couldn't actually find anyone who has done #3....

I just did a Roth conversion yesterday at Wells Fargo, and found there's no way to accomplish your #3 there (I didn't want to do that anyway, it's just something I noticed). Their conversion form actually tells you that if you want to withhold taxes, you should make a separate withdrawal from your IRA and have 100% of that withheld.
 
I just did a Roth conversion yesterday at Wells Fargo, and found there's no way to accomplish your #3 there (I didn't want to do that anyway, it's just something I noticed). Their conversion form actually tells you that if you want to withhold taxes, you should make a separate withdrawal from your IRA and have 100% of that withheld.

Thanks Cathy. As I mentioned before, it can be done at Fidelity but requires that you call in and have a rep do it for you. They like to verify that you are over 59.5, so no 10% penalty on the withholding portion. They also like to advise people to use taxable funds for the tax in order to maximize the conversion amount.

However, if possible, I'd like your expert opinion on the second part of #3...

...

3. Do the $100K Roth conversion. Withhold $22K during the conversion transaction. Net conversion amount is $78K. To complete the conversion, replace the $22K in the Roth within 60 days from non-retirement funds...

Another poster commented that the replacement $22K would be seen as a "contribution" to the Roth, not a "completion of the conversion", as it is characterized in the fairmark thread that I linked to earlier. Is there some mechanism to explain to the IRS that the $22K is a conversion rather than a contribution? The folks on the fairmark thread seem pretty confident that this method is commonplace but offer no details on the mechanics. Thanks.
 
...Another poster commented that the replacement $22K would be seen as a "contribution" to the Roth, not a "completion of the conversion", as it is characterized in the fairmark thread that I linked to earlier. Is there some mechanism to explain to the IRS that the $22K is a conversion rather than a contribution? The folks on the fairmark thread seem pretty confident that this method is commonplace but offer no details on the mechanics. Thanks.

Here's the Fidelity Deposit Slip: https://www.fidelity.com/bin-public/060_www_fidelity_com/documents/customer-service/deposit-slip.pdf

I have never done this, but I don't see why you wouldn't be able to enter the Roth account number in part 1 and then check the box that says 60-day Rollover in part 2.

This is one of the methods the IRS describes for doing a rollover, so I don't see why it couldn't be done at any IRA custodian or why a Roth IRA should be different than a traditional IRA. The custodian doesn't have to know where you originally got the funds from. They should just take your word for it if you say it's a rollover.

https://www.irs.gov/retirement-plan...vers-of-retirement-plan-and-ira-distributions
60-day rollover – If a distribution from an IRA or a retirement plan is paid directly to you, you can deposit all or a portion of it in an IRA or a retirement plan within 60 days. Taxes will be withheld from a distribution from a retirement plan (see below), so you’ll have to use other funds to roll over the full amount of the distribution.
 
You are never required to fill out form 2210. The IRS is happy to calculate the penalty for you by assuming that your income was spread equally through the year. :(

However, Cobra is correct that you can still owe a penalty for underpayment even if you reach the safe harbor. See https://www.irs.gov/instructions/i2210



The key word there is "timely". Making the full safe-harbor payment as a Q4 estimate won't negate the penalty.

I think the IRS doesn't actually issue penalties in most cases though. I suspect that they really only do the math if they're looking at your return for some other reason or if you filed late and the balance due was a large percentage of the total tax. We get a lot of folks at our Tax-Aide site whose returns get the "might have a penalty" message, and even when I know they actually should owe a penalty, they usually come back the next year and say they never heard anything from the IRS.


How does turbo tax handle safe harbor? For 2020 I did not verify safe harbor and TT calculated a small Fed penalty and also generated the estimated 2021 quarterly payments that I did not pay. I will do a December 2021 tIRA distribution with 99% withholding to meet safe harbor requirements. I’m hoping after I enter all 2021 1099s TT will figure no penalty even though I did not make the quarterly payments.
 
How does turbo tax handle safe harbor? For 2020 I did not verify safe harbor and TT calculated a small Fed penalty and also generated the estimated 2021 quarterly payments that I did not pay. I will do a December 2021 tIRA distribution with 99% withholding to meet safe harbor requirements. I’m hoping after I enter all 2021 1099s TT will figure no penalty even though I did not make the quarterly payments.

If you import your 2020 tax file when you start this year's return, then TT will be able to figure out whether you met the safe harbor rules in 2021 or not. Otherwise, if you start a new return with no import and you owe more than $1K, it will ask you for the numbers on lines 11 and 16 of last year's 1040 and use those to figure out whether you owe a penalty or not.
 
Here's the Fidelity Deposit Slip: https://www.fidelity.com/bin-public/060_www_fidelity_com/documents/customer-service/deposit-slip.pdf

I have never done this, but I don't see why you wouldn't be able to enter the Roth account number in part 1 and then check the box that says 60-day Rollover in part 2.

This is one of the methods the IRS describes for doing a rollover, so I don't see why it couldn't be done at any IRA custodian or why a Roth IRA should be different than a traditional IRA. The custodian doesn't have to know where you originally got the funds from. They should just take your word for it if you say it's a rollover.

https://www.irs.gov/retirement-plan...vers-of-retirement-plan-and-ira-distributions

Thanks very much Cathy. But if I check 60-Day Rollover, that counts toward my once-per-year limit. The "advertised" advantage of #3, as discussed on the fairmark thread, is that it's a conversion, not a rollover, and thus not subject to that limitation. More importantly, the rollover would be non-taxable, which is not the intent. The whole $100K conversion should be taxable.

Another option on that paper deposit form is "Roth Conversion." I think that's the one I want to check. But it seems a bit odd to deposit a check from my CMA, into a Roth, and characterize it as a "Roth Conversion." But I think that's exactly what that fairmark thread discussion was all about...

1. Convert $100K and withhold $22K (net conversion $78K)
2. Deposit $22K from taxable into Roth, to "complete the conversion."

Sounds doable and legit to me. But I'd love to hear your opinion.
 
I can assure you that I asked multiple ways and used the phrase “Just to be absolutely clear,…” (this was a Chat, BTW) and he assured me and I repeated it to him. If it turns out to be incorrect, then he basically was talking out of his a$$. No doubt, for this conversion, I will call in and do it with their assistance. It should NOT be this hard to pay the taxes and avoid a roll-over!!!
 
Thanks very much Cathy. But if I check 60-Day Rollover, that counts toward my once-per-year limit. The "advertised" advantage of #3, as discussed on the fairmark thread, is that it's a conversion, not a rollover, and thus not subject to that limitation. More importantly, the rollover would be non-taxable, which is not the intent. The whole $100K conversion should be taxable.

Another option on that paper deposit form is "Roth Conversion." I think that's the one I want to check. But it seems a bit odd to deposit a check from my CMA, into a Roth, and characterize it as a "Roth Conversion." But I think that's exactly what that fairmark thread discussion was all about...

1. Convert $100K and withhold $22K (net conversion $78K)
2. Deposit $22K from taxable into Roth, to "complete the conversion."

Sounds doable and legit to me. But I'd love to hear your opinion.

You can make multiple tIRA to Roth IRA conversions in the same year. All conversions are treated as rollovers and there's no limit on them, so marking the rollover box on the deposit form theoretically shouldn't prevent you from doing another rollover within a year. See the following quotes from Pub 590-A where I highlighted the relevant text in red (these are from the 2020 pub, but I don't think the 2021 version is going to say anything different about this topic).

Application of one-rollover-per-year limitation. You can make only one rollover from an IRA to another (or the same) IRA in any 1-year period regardless of the number of IRAs you own. The limit will apply by aggregating all of an individual's IRAs, including SEP and SIMPLE IRAs as well as traditional and Roth IRAs, effectively treating them as one IRA for purposes of the limit. However, trustee-to-trustee transfers between IRAs aren’t limited and rollovers from traditional IRAs to Roth IRAs (conversions) aren’t limited.

Conversions

You can convert a traditional IRA to a Roth IRA. The conversion is treated as a rollover, regardless of the conversion method used. Most of the rules for rollovers, described in chapter 1 under Rollover From One IRA Into Another, apply to these rollovers. However, the 1-year waiting period doesn’t apply.

Conversion methods. You can convert amounts from a traditional IRA to a Roth IRA in any of the following three ways.
* Rollover. You can receive a distribution from a traditional IRA and roll it over (contribute it) to a Roth IRA within 60 days after the distribution.
* Trustee-to-trustee transfer. You can direct the trustee of the traditional IRA to transfer an amount from the traditional IRA to the trustee of the Roth IRA.
* Same trustee transfer. If the trustee of the traditional IRA also maintains the Roth IRA, you can direct the trustee to transfer an amount from the traditional IRA to the Roth IRA.

Now, Fidelity may say that you should check the Roth Conversion box as you suggest instead of the Rollover box for these transactions. It's their form and their computer system, so you should do whatever they tell you to do in this case. It's possible that their system would reject a second form for the same account that has the rollover box checked within a year.

For tax docs, you are going to get a 1099-R for the full amount of the withdrawal from the tIRA. The box for "taxable amount not determined" should be checked, and box 7 should either have a 2 or 7 in it, depending on how old you are. Box 4 will show the income tax withheld.

You and the IRS are not going to get anything that shows deposits into the Roth account until 5498s are issued in May. That's where a rollover gets reported in box 2 and the conversion in box 3. I really don't think it's going to cause any kind of headache if the conversion is split over those two boxes. The taxes are all figured off the 1099-R.
 
You are never required to fill out form 2210. The IRS is happy to calculate the penalty for you by assuming that your income was spread equally through the year. :(

However, Cobra is correct that you can still owe a penalty for underpayment even if you reach the safe harbor. See https://www.irs.gov/instructions/i2210

The key word there is "timely". Making the full safe-harbor payment as a Q4 estimate won't negate the penalty.

I think the IRS doesn't actually issue penalties in most cases though. I suspect that they really only do the math if they're looking at your return for some other reason or if you filed late and the balance due was a large percentage of the total tax. We get a lot of folks at our Tax-Aide site whose returns get the "might have a penalty" message, and even when I know they actually should owe a penalty, they usually come back the next year and say they never heard anything from the IRS.

Right.

I had a long conversation with one of the more senior Tax Aide people in my district about this topic this morning.

She and I agreed that there were income / withholding / estimated payment patterns which would fail the "timeliness" criteria, could result in a refund to the taxpayer, and would not be discernable to the IRS unless they looked at the actual timing of things.

In these scenarios, she further agreed that the taxpayer should in theory notify the IRS of the underpayment situation and pay a penalty. But she also said she's never seen that happen. I imagine that if a TP either naively doesn't file a Form 2210 or deliberately ignores such a situation, the IRS, as you say, wouldn't investigate for that reason alone, and does not generally assess an underpayment penalty as long as the annual numbers meet an annual safe harbor amount.

As an aside, I've been informed that underpayment penalties are out of scope and that we're not supposed to prepare such returns for Tax Aide. But unless the TP says something, or the counselor observes an unusual pattern of income or withholding or estimated payments, I doubt such a situation would be caught by most of us here. I'm a bit surprised that your area is allowed to proceed in that scenario.
 
Right.

I had a long conversation with one of the more senior Tax Aide people in my district about this topic this morning.

She and I agreed that there were income / withholding / estimated payment patterns which would fail the "timeliness" criteria, could result in a refund to the taxpayer, and would not be discernable to the IRS unless they looked at the actual timing of things.

In these scenarios, she further agreed that the taxpayer should in theory notify the IRS of the underpayment situation and pay a penalty. But she also said she's never seen that happen. I imagine that if a TP either naively doesn't file a Form 2210 or deliberately ignores such a situation, the IRS, as you say, wouldn't investigate for that reason alone, and does not generally assess an underpayment penalty as long as the annual numbers meet an annual safe harbor amount.

As an aside, I've been informed that underpayment penalties are out of scope and that we're not supposed to prepare such returns for Tax Aide. But unless the TP says something, or the counselor observes an unusual pattern of income or withholding or estimated payments, I doubt such a situation would be caught by most of us here. I'm a bit surprised that your area is allowed to proceed in that scenario.

No, we don't file form 2210 even if we know there's a penalty due. That is definitely out of scope. Returns can always be filed without a 2210 though since the IRS doesn't require the TP to figure out their own penalty, so we do them as long as the rest of it is in scope.

Usually it's not something we catch ourselves, but TaxSlayer will pop up a message saying there may be a penalty due whenever someone owes more than $1K and hasn't met the 90% threshhold. It doesn't look at the prior year return, so sometimes that message is incorrect. We just explain the message to the TP and tell them if they get a letter from the IRS about a penalty, they should pay attention to it and respond. This usually happens a couple times a day at our site. The population we serve has a lot of people with several part-time or temp jobs, and some unemployment or SS, and maybe they're also an Uber driver on the side, so they're making ends meet but just don't have enough withholding. As I said before, they usually come back the next year and say they never heard from the IRS, so that's why I don't think the IRS is really looking for people to penalize, especially at the lower income levels.
 
^ Interesting. I've always been told that we don't do returns with an underpayment penalty because they're out of scope. But in actual fact (per the scope manual) what is (almost entirely) out of scope is F2210. Which makes more sense. Thanks.
 
Rayvt says: “ additionally, you'd perhaps like to pay the withholding from your regular taxable account instead of your tIRA. But you can't do a withholding from a taxable account withdrawal, only from a tIRA withdrawal.”

Why do you say that? That is not what Fidelity said at all. In fact, that is exactly how they recommended paying taxes for the Roth conversion; via a distribution from a taxable account such as a brokerage account and specify 100% withholding.

Taking money from a normal taxable account is not a "distribution", it is a withdrawal.

I just did a trial withdrawal from a taxable account at Etrade, and there is no place to specify a withholding.

A search on "withholding distribution from a taxable account" yields this from Schwab: " In most instances, taxes are not withheld from capital gains, distributions, or other income generated from such accounts.2 However, you may want to withhold more elsewhere or pay quarterly estimated taxes to help cover any tax liabilities produced by these assets.

2Certain taxpayers may be subject to backup withholding, which requires a payer to withhold tax from payments not otherwise subject to withholding."

I think either you or the Fidelity person misunderstood the question & answer.
 
I can assure you that I asked multiple ways and used the phrase “Just to be absolutely clear,…” (this was a Chat, BTW) and he assured me and I repeated it to him. If it turns out to be incorrect, then he basically was talking out of his a$$.

I cannot count the number of times I have talked to a person at a broker (multiple brokers, not just one) and gotten a firm answer that I knew was incorrect. If you are asking about a non-trivial issue, often you know more about the issue than the broker person does.

The first level of phone support consists of Telephone Answerers, not subject matter experts.

A couple of time when I was asking about an IRA related issue, they said that they were sure their answer was right (it wasn't) but they would need to bring in someone from the "Retirement Account Team". Both times, that person gave the right answer and corrected what the phone answerer person had said.
 
Here is my update to my situation. (Nothing compelling here, just closing the loop.)

I am grateful to cobra, SecondCor, and Cathy for shedding the necessary light on this. I realized that I had a tool that I did not mention in my first post because I did not think it relevant: I also have tax-deferred money in 403(b) plans that I do have access to under the Rule of 55. As SecondCor pointed out, there is no one-year restriction of transfers from 403 to IRA, and there is no 10% penalty to worry about.

So, today I converted $54k from a VG IRA to a VG Roth IRA. I also took a distribution of $12k from my 403(b) with 99% withholding. This amount should get me to safe harbor, or at least be damn close. I intend to make a rollover contribution of $12k from taxable to my tIRA in the next few days.

Thanks everyone for your help and insight.
 
Originally Posted by Cobra9777
...if done late in the year, with the $22K replaced in Jan of the following year, the entire $100K is taxable in the first year, while the 5-year holding period is based on the year of contribution, which might require some careful record-keeping...
The 5 years for Roth withdrawal is based on the date when the Roth was established (by a conversion or contribution), not on the date of this contribution.

As long as you are over 59 1/2, the date of this contribution/rollover does not matter because there is no penalty if you are over 59 1/2.
 
After reading the whole thread, I'm left wondering why the reluctance to figuring your own penalty and having it be zero (using form 2210).

IMO, it's WAY less trouble, and less record-keeping, to print a January estimated tax form, mail off a check, followed by a few tax software interview questions that generate a 2210 that eliminates the penalty, than it is to fiddle around trying to restore funds back to a tax advantaged account, with all of rules (with various interpretations) and potential gotchas.
 
After reading the whole thread, I'm left wondering why the reluctance to figuring your own penalty and having it be zero (using form 2210).

IMO, it's WAY less trouble, and less record-keeping, to print a January estimated tax form, mail off a check, followed by a few tax software interview questions that generate a 2210 that eliminates the penalty, than it is to fiddle around trying to restore funds back to a tax advantaged account, with all of rules (with various interpretations) and potential gotchas.
Speaking from experience, it's WAY easier to use EFTPS to set up quarterly payments for the tax year than to fill out for 2210. I make 4 even payments which are 1/4 of my total tax from the year before, giving me safe harbor. If for some reason I had a lot higher than normal income the year before, I make a good estimate for the next year. I can always go in and change the payments if needed.

I can't say whether the withholding method is easier than yours, but I would try it before knowingly subjecting myself to "fiddling around" with form 2210.
 
If you are retired and have a tIRA, it is easier to do one large distribution near the end of the year with a large safe harbor withholding.
You don't have to have the cash available like you do for quarterly estimated tax payments, even EFTPS. You don't even need for cash to be available at all---it just comes out of your IRA distribution.

Whether you want to restore the money back into the IRA by doing a 60 day rollover is up to you. It doesn't really matter, because all the money in your tIRA is going to get taxed at sometime or another.
 
If you are retired and have a tIRA, it is easier to do one large distribution near the end of the year with a large safe harbor withholding.
You don't have to have the cash available like you do for quarterly estimated tax payments, even EFTPS. You don't even need for cash to be available at all---it just comes out of your IRA distribution.

Whether you want to restore the money back into the IRA by doing a 60 day rollover is up to you. It doesn't really matter, because all the money in your tIRA is going to get taxed at sometime or another.


This thread has been very informative. A question I have about restoring the money via 60-day rollover contribution from taxable account back to tIRA, are the transferred funds still considered deductible funds?
 
A question I have about restoring the money via 60-day rollover contribution from taxable account back to tIRA, are the transferred funds still considered deductible funds?

No. The money transferred back is just that---putting the money back. It is not a contribution and hence is not deductible.

BTW, I did a Roth conversion this morning at Etrade. They do allow you to do a withholding along with the conversion. No need to call and talk to anyone, it's just a field in the form. You tell it that you want to transfer "securities and cash". Minimum withholding is 10%.

======================
After thinking about all this for a few days, it has become clear the only benefit for doing any of this is for the withholding to get you to the safe harbor. Whether you withhold from an IRA withdrawal or a Roth conversion does not matter. You have to pay tax on the withdrawal from the IRA, payable next April either way.

There is no free lunch here.

If you do the 60 day rollover back to the tIRA you have just made the estimated tax payment with non-IRA funds via the IRA to make it a withholding instead of a quarterly payment. The sole benefit of this is to get you to the safe harbor.

A slight benefit is that if you complete the 60 day rollover in January/Feb of the next year and it is an RMD year, then you can use money that you take out as RMD to pay it back. Note: this is not rollover of the RMD withdrawal, this is completing the outstanding rollover.
 
We do a large Roth conversion every December. To cover the tax and meet safe harbor, I've done all 3 of these methods in the past:

1. Four equal EFTPS payments throughout the year.
2. Large EFTPS payment in January + F2210 to avoid penalty.
3. Dec tIRA withdrawal w/ 99% WH + repay from taxable w/in 60 days.

In my experience, they're all fairly easy. The disadvantage of #1 is I'd pay too much, too early. The disadvantage of #2 is F2210, which adds an hour or two to return prep. For me, #3 is just as easy as #1 and avoids both disadvantages.

Granted, neither of those disadvantages is a huge deal. But since there is a better way, that's the method I prefer.
 
No. The money transferred back is just that---putting the money back. It is not a contribution and hence is not deductible.

BTW, I did a Roth conversion this morning at Etrade. They do allow you to do a withholding along with the conversion. No need to call and talk to anyone, it's just a field in the form. You tell it that you want to transfer "securities and cash". Minimum withholding is 10%.

======================
After thinking about all this for a few days, it has become clear the only benefit for doing any of this is for the withholding to get you to the safe harbor. Whether you withhold from an IRA withdrawal or a Roth conversion does not matter. You have to pay tax on the withdrawal from the IRA, payable next April either way.

There is no free lunch here.

If you do the 60 day rollover back to the tIRA you have just made the estimated tax payment with non-IRA funds via the IRA to make it a withholding instead of a quarterly payment. The sole benefit of this is to get you to the safe harbor.

A slight benefit is that if you complete the 60 day rollover in January/Feb of the next year and it is an RMD year, then you can use money that you take out as RMD to pay it back. Note: this is not rollover of the RMD withdrawal, this is completing the outstanding rollover.


Understood, I wasn’t thinking of claiming a deduction. The point of my question was related to the fact that a tIRA can accept both deductible and nondeductible funds when contributing to it. In my case, my IRA only has deductible funds in it from work place rollovers etc. I never contributed nondeductible funds and want to keep it that way.

In this tread we’ve been using the term rollover/contribution for putting the money back into the IRA from taxable account. I guess I wasn’t clear on if it was treated as a contribution. So are we saying since it’s a 60-day-rollover, by definition we are replacing same type funds that were removed from tIRA?
 
Yes, the transactions for this on Fidelity are no big deal. Do a regular tIRA withdrawal, but specify 99% withholding. So, 99% of the withdrawal goes directly to the US treasury, …..

When your 1099-R arrives, it will show the gross distribution and withholding, with a box checked that says "Taxable amount not determined." In TurboTax, specify that you paid back the distribution as a rollover. It will reduce your gross distributions accordingly and print the word "ROLLOVER" on line 4b to explain the difference. All the records of this are in one place at Fidelity.

BTW, there's an interesting variation on this method that uses a Roth IRA... Do your normal Roth conversion and withhold whatever amount you want for taxes. Then repay that amount into the Roth within 60 days from taxable funds. This achieves the same result, but has one distinct advantage... it is not subject to the one-rollover-per-year limitation since it is a conversion.


In case anyone revisits this thread, this last paragraph apparently does not work. After I transferred the amount I wanted from my tIRA to my Roth, I wanted to pay the taxes with after tax funds. I tried, both on line and with a Fidelity representative. As rayvt mentioned in another thread, there is no way to withdraw funds from a taxable account with withholding, which is what the first Fidelity rep incorrectly told me. There is also no way to move money from an after tax account in to a Roth without it being considered a contribution. When we did it from a tIRA, it was easily categorized as ROLLOVER. So I just have to make sure I do next years one day later, and so on, since only one rollover is allowed per 12 month period. I will be done with conversions before I run out of days left in December so that will work out ok.
 
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