One IRA contribution was non-deductible, but no records

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GrowthSeeker
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Joined: Tue May 15, 2018 10:14 pm

One IRA contribution was non-deductible, but no records

Post by GrowthSeeker » Mon Jun 11, 2018 8:11 am

Hello all, I am new to Bogleheads looking to reorganize my finances that are spread among half a dozen taxable and half a dozen IRA accounts. But before getting into all that complexity, I have a simple question to start with.
I am 65, retired, with about one quarter of one percent of my IRA money having been non-deductible (no Roth accounts). Or so I think. It was in 1986 when the IRS changed the rules so that if you were covered by an employer pension, you could still contribute to the IRA but it had to be with post-tax dollars. So I think a made a $2,000 non-deductible, after tax, IRA contribution just once, probably in '86 or '87. But I don't have tax records for that year. I will assume that my accountant filed correctly that year, but there has been no Form 8606 filed in recent years keeping track of that remote one-time contribution.

In my mind, the pain of paying double taxation on such a small amount of money is much smaller than the pain of having to file an extra form and calculate the percent moving forward once I start taking RMDs in 5 or 6 years, and then repeating the headache every year for the rest of my life. My back of the envelope calculations suggest I'll be overpaying my taxes by about $20/year.

Questions:
1. Let's assume for Question One, that I actually do end up having to go through with the annual form 8606 headache. The IRA which had that one non-deductible contribution currently has only $17K in it or so. I have been keeping that separate not wanting to "mix" it with the other IRAs which were rolled over from various qualified plans. For years I believed that a simple IRA account should not be mixed with money from a qualified pension plan. Now I don't believe that is true. Having recently re-read the IRA Aggregation Rule, it looks like there would be no negative consequence if I transfer assets from other rollover IRA accounts into this "tainted" IRA account. Am I correct here? This is my main concern now, can I mix these accounts?

2. One of my IRAs is a SEP-IRA from when I was self-employed. Can I transfer these assets into the simple IRA account, can I mix these accounts?

3. If (in 5 or 6 years when I take my first RMD) I simply act as though all my IRA money was pre-tax, will the IRS computer crunch through it's records from 1986 and realize my mistake and send me a notice that I overpaid them and need to file more forms?

4. For completeness and educational purposes, if I were to file as if I was certain that I made a $2,000 non-deductible IRA contribution in 1986 what would I need to do to prove that (since I have no records from then)? Would simply filling out Form 8606 to the best of my recollection be OK?

Thanks!

Spirit Rider
Posts: 7980
Joined: Fri Mar 02, 2007 2:39 pm

Re: One IRA contribution was non-deductible, but no records

Post by Spirit Rider » Mon Jun 11, 2018 10:41 am

You only file a form 8606 for any given year when it is required:
  • You made nondeductible contributions to a traditional IRA in the current year.
  • You took distributions from a traditional, SEP, or SIMPLE IRA in the current year and you made nondeductible contributions to a traditional IRA in the current or earlier year.
  • You converted part, but not all, of your traditional, SEP, and SIMPLE IRAs to Roth IRAs in the current year.
The Tax Reform Act of 1986 first allowed non-deductible contributions for the 1987 tax year. If you made a non-deductible contribution for 1987, filed a 1987 Form 8606 and never met one of the above conditions. There was never a reason to file another Form 8606.
  1. All of your balances in all traditional, SEP, and SIMPLE IRA accounts are treated as one.
  2. Yes, your can rollover your SEP IRA to another IRA. In fact you can consolidate all your IRAs to one IRA. Per chance do you have assets in the TSP or another 401k/403b/457 that accepts IRA rollover contributions. If so you could rollover all pre-tax balances in all traditional, SEP, or SIMPLE IRA accounts. Leaving just the non-deductible basis to convert to a Roth IRA. If not and you can generate even a modest amount of self-employment income. You could adopt a one-participant 401k that accepts IRA rollover contributions (not Vanguard) and do the same thing. Then the following year (not the same year as the Roth conversion). You could roll the balance back to a traditional IRA if you so choose.
  3. There is another thread about unknown non-deductible basis in Inherited IRAs covering this issue. It is unlikely the IRS will care in your circumstances, but they do have specific guidance that you must take all available deductions available to you. However, to my knowledge the IRS only taken action if you derive a benefit from the increased income. It most commonly is applied to self-employed individuals:
    • Earned Income Credit (EIC). For each additional dollar in earned income below the maximum EIC, you gain a $.40 increase in EIC more than offsetting any increase in SE taxes and you will have little to no income tax liability <= 15%. This is the big one, the IRS will even sanction tax preparers for not doing due diligence to make sure this is not happening.
    • You receive increased Social Security earnings credits, most valuable if your AIME will be < the 2nd SS bend point.
    • Additional employer retirement plan contributions.
    • Etc...
  4. You can request a transcript of your 1987 tax return. Regardless if there is Form 8606 or not, whether you want to claim the basis is between you and your conscience. You do sign under the penalty of perjury that your income tax return is correct to the best of your knowledge. Forum policy is against tax evasion, by I don't think it applies to voluntarily paying more tax than your obligated to. If the transcript shows no Form 8606 and you would like to claim the basis, you can file a retroactive 1987 Form 8606 now. I would feel comfortable doing so given the degree of your certainty.

GrowthSeeker
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Joined: Tue May 15, 2018 10:14 pm

Re: One IRA contribution was non-deductible, but no records

Post by GrowthSeeker » Tue Jun 12, 2018 2:13 pm

Thank you Spirit Rider for that information, I appreciate your time and helpfulness.
I've now spoken to 3 folks at Etrade and 2 at Vanguard plus more research.
I even tried to call IRS but couldn't get past the phone tree.

To clarify my concern for this post:
(a) what IRAs can be combined (I believe this has been answered to my satisfaction [solved]);
(b) what to do about the small amount of IRA money that was made with after tax money. I really don't want to have to deal with Form 8606 every year from age 71 until the end of days. I look at it as though the non-deductible contribution "tainted" the Traditional IRA but the Aggregation Rule taints either some or all of the other IRAs as well (ie definitely the SEP maybe or maybe not the Rollovers)

I am probably going to ignore the after tax basis and just bite the bullet and overpay taxes but there is still a chance IRS with "catch" me paying too much and insist that I pay them less tax but fill out more forms. So I'm still looking at ways to "get rid of" the problem. Plus the last 24 hours of research and Spirit Rider's post have me thinking further.

A few more details:
Age 65, file single; tax bracket 22%; Ohio
Retired. No plans to work again.
Zero debt.

A total of 5 IRAs (none of them Roth):
Traditional IRA at Vanguard: $17K ($2,000 non deductible basis which I can't prove)
SEP-IRA at Etrade: $83K (from when I was the sole employee of a corporation of which I was the President)
3 Rollover IRAs one each at Etrade, TDA, Fidelity (total $700K) all from various employer sponsored plans originally.
Total of all 5 IRAs about $800K

I never worked for the government and have no TSP

Earned income I have for 2018 is about $17K of disability insurance which was from an employer sponsored insurance plan (where I was a salaried employee), so I have to pay tax on this income, it comes on a W2. Only other income is SS ($30K) and investment income.
Earned income for 2019 and beyond will be zero.

Further thoughts:

1. Re a possible 8606 from 1987, I have read that IRS does not keep tax returns from that far back, but what I don't know is if they carry forward each tax payer's 8606 non deductible IRA basis from each year to the next.
2. I still don't know for sure if the Rollover IRAs (about $700K) are part of the Aggregation. If they are NOT, then I could purify the SEP, turn the Traditional IRA into a Roth and only have to worry about the post tax basis during one tax filing.
3. If the entirety of my IRAs is included in the Aggregation, there is no way to escape from filing Form 8606 from age 71 and beyond, except to ignore it, pay a tiny amount of double tax and hope IRS doesn't notice or care.
4. I believe I could make a solo 401k based on the $18K of "earned income". But AFAIK, I do not have a separate EIN anymore. If for some reason that earned income "doesn't qualify" regarding a 401k, then I don't know if I can make a solo 401k based on nothing. Probably not.
5. I understand I can "purify" a pre-tax SEP by rolling it into a 401k (assuming I can form one); then it would be removed from the denominator in the IRA Aggregation formula
6. Even if I can't make a 401k, as long as the bulk of my IRAs (the Rollovers) are not in the Aggregation mix, I could convert the SEP and the Traditional to Roth (total is about $100K) gradually over the next few years.
7. A separate issue is, I can and should make a Roth IRA this year and put in $6,500 of after tax money.

Spirit Rider
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Re: One IRA contribution was non-deductible, but no records

Post by Spirit Rider » Tue Jun 12, 2018 3:29 pm

GrowthSeeker wrote:
Tue Jun 12, 2018 2:13 pm
1. Re a possible 8606 from 1987, I have read that IRS does not keep tax returns from that far back, but what I don't know is if they carry forward each tax payer's 8606 non deductible IRA basis from each year to the next.
Yup, forgot six years only.
2. I still don't know for sure if the Rollover IRAs (about $700K) are part of the Aggregation. If they are NOT, then I could purify the SEP, turn the Traditional IRA into a Roth and only have to worry about the post tax basis during one tax filing.
There is no exception for rollover IRAs. IRS 2017 Form 8606 Line 6; "Enter the value of all your traditional, SEP, and SIMPLE IRAs as of December 31, 2017." Emphasis IRS
3. If the entirety of my IRAs is included in the Aggregation, there is no way to escape from filing Form 8606 from age 71 and beyond, except to ignore it, pay a tiny amount of double tax and hope IRS doesn't notice or care.
Or rollover.
4. I believe I could make a solo 401k based on the $18K of "earned income". But AFAIK, I do not have a separate EIN anymore. If for some reason that earned income "doesn't qualify" regarding a 401k, then I don't know if I can make a solo 401k based on nothing. Probably not.
Getting an EIN is ten minutes online. Only required by some providers. Not needed for Schedule C. If you were previously self-employed in any prior year. There is no requirement to have current year self-employment to adopt a 401k.
5. I understand I can "purify" a pre-tax SEP by rolling it into a 401k (assuming I can form one); then it would be removed from the denominator in the IRA Aggregation formula.
All pre-tax IRA balances can be rolled over, not just the SEP IRA. Make sure they accept IRA rollovers (not Vanguard.)
6. Even if I can't make a 401k, as long as the bulk of my IRAs (the Rollovers) are not in the Aggregation mix, I could convert the SEP and the Traditional to Roth (total is about $100K) gradually over the next few years.
They absolutely are.
7. A separate issue is, I can and should make a Roth IRA this year and put in $6,500 of after tax money.
If you have sufficient W-2 Box 1 wages and/or net self-employment earnings, Roth IRA contributions are always a good idea.

Alan S.
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Re: One IRA contribution was non-deductible, but no records

Post by Alan S. » Tue Jun 12, 2018 3:47 pm

All things considered, I would simply spurn the 8606 if you want to. Roughly, I come to about $73 of increased taxable income if your first RMD on a balance of 800k was due this year (if you were 70.5 now). A 2,000 basis is .25% of your balance, and that will drop further if your balance grows the next 5 years. Your choice, and you have 5 years to make a decision, but once made I would stick with it for all later years.

There is no chance the IRS will ever question the lack of an 8606 with your returns. I have yet to see them even question the AMOUNT of basis reported on lines 1 or 2 of Form 8606, or NOT reported on those lines. As bad as ordinary taxpayers are in accurately tracking their IRA basis, the IRS is no better. Probably a casualty of operating with outdated technology the last 3 decades.

Yes, I know the funds have been allocated to upgrade systems based on the recent tax bill. But there is no way they are going to spend any time trying to reconstruct someone's actual tax basis from the 20th century.

retiredjg
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Re: One IRA contribution was non-deductible, but no records

Post by retiredjg » Wed Jun 13, 2018 1:56 pm

I'll share my experience.

I've only used a tax-preparer once in my life. I thought it was 1986 but I guess it was 1987 based on Spirit Rider's post. The tax preparer didn't ask and I didn't know to tell him about my $2k non-deductible contribution to tIRA. No Form 8606 got filed that year.

The following few years, I did file Form 8606. Then Roth IRA came along and I didn't contribute to tIRA again after that.

Fast forward into retirement and overhaul of my portfolio about 2009 or 2010. Using Boglehead's guidance, I isolated my recorded basis from my IRA and converted it to Roth. I wasn't thrilled about it but could not worry about the unrecorded $2k basis - I didn't know at that time that old Forms 8606 could still be filed.

The last Form 8606 I sent in (when I did the Roth conversion) indicated $0 basis. I've never heard from the IRS about having basis that was not converted. I doubt they care if I pay a few dollars extra in taxes. They have real problems to worry about. Also, it is not their job to remind me of my own documentation responsibilities.

If I use all my IRA before I die, I'll pay tax a second time on that $2k. But if I get down the the last $2k in my IRA before I die, I don't think it will make a lot of difference if I pay tax on it or not. :D

PS, I'm happy that I don't have to use Form 8606 every year. In fact, I'm now using the short form. That's nice.

JW-Retired
Posts: 6755
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Re: One IRA contribution was non-deductible, but no records

Post by JW-Retired » Wed Jun 13, 2018 4:20 pm

retiredjg wrote:
Wed Jun 13, 2018 1:56 pm
If I use all my IRA before I die, I'll pay tax a second time on that $2k. But if I get down the the last $2k in my IRA before I die, I don't think it will make a lot of difference if I pay tax on it or not. :D

PS, I'm happy that I don't have to use Form 8606 every year. In fact, I'm now using the short form. That's nice.
Agree not a lot of difference.... but Form 8606 in the withdrawal phase is awfully trivial.

DW has something like a 10% non-deductible basis in her IRA, but our low expense tax software does all the work with Form 8606 for us. The first time we withdrew from the IRA we did need to supply the non-deductible basis to the software. All the several years after that, the software just reads her account 1099-R, figures & files the 1040, and updates it's basis data for the next year automatically.

I confess we never give more than a quick glance at the 8606. :P
JW
Retired at Last

GrowthSeeker
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Joined: Tue May 15, 2018 10:14 pm

Re: One IRA contribution was non-deductible, but no records

Post by GrowthSeeker » Thu Jun 14, 2018 8:01 am

Appreciate those last comments retiredjg and JW-Retired. Part of my mental calculus here is that I haven't done my own taxes since 1983, but now that life is simpler I was thinking of resuming doing my own taxes within a few years. But it looks like I have been underestimating the benefit of tax software in taking away the headache of filling out forms.

Still, (in addition to putting 6500 into a new Roth IRA for 2018), I could do the following:
* start a solo 401k for 2018;
* roll the 3 rollover IRAs and the SEP-IRA into it;
* file a form 8606 for 1987;
* convert the $17K tIRA into Roth, taking credit for the $2,000 non deductible basis.

I don't know of a downside.

1. I think I would have to do the Roth conversion in 2019 not 2018, correct?

2. Later, I could always roll the 401k to an IRA; or move it to another brokerage; or convert some fraction of it to a Roth IRA (or theoretically a Roth 401k), correct?

3. Candidates for the location of the new 401k: Etrade, Fidelity, TDAmeritrade (not Vanguard). Anyone know of good reasons pro or con any of these three? (Clearly I have to call and verify that they accept rollovers into indiv 401k.)

retiredjg
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Re: One IRA contribution was non-deductible, but no records

Post by retiredjg » Thu Jun 14, 2018 8:32 am

It would not be "wrong" to do that. If it makes you feel better, do it.

The downside is your time and effort for doing it and the cost, if any, of the Solo 401k. And the tax cost of the Roth conversion. This could be avoided by rolling all but the $2k into the Solo.

You can do the Roth conversion in 2018 if you want. If you want to avoid pro-rating, you must have nothing in tIRA (including rollover, SEP, and SIMPLE) at the end of the year that you do the conversion.

Yes, later (after 2018) you could roll the money back to IRA. And convert whatever you want to Roth.

It would not be worth it to me. You are contemplating 4 or 5 rollovers and a roth conversion followed by a later rollover. If you are in the 25% tax bracket till the end of your days, the most you would save is $500. If you don't spend your entire IRA before you die, I guess you save nothing.

I would use Fidelity. When Vanguard can't be used, I think Fidelity would be my favorite choice.

ryman554
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Re: One IRA contribution was non-deductible, but no records

Post by ryman554 » Thu Jun 14, 2018 8:43 am

retiredjg wrote:
Thu Jun 14, 2018 8:32 am
It would not be worth it to me. You are contemplating 4 or 5 rollovers and a roth conversion followed by a later rollover. If you are in the 25% tax bracket till the end of your days, the most you would save is $500. If you don't spend your entire IRA before you die, I guess you save nothing.
I agree with your first statement, but am a bit perplexed by the last statement. You save tax (proportionately) all the way down as, assuming no investment growth, the ratio of the basis to account balance is unchanged on form 8606 during withdrawal phase. With investment growth, I guess this ratio declines, but it's not like a step function of saving turns on at the last $2000 or so.

retiredjg
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Joined: Thu Jan 10, 2008 12:56 pm

Re: One IRA contribution was non-deductible, but no records

Post by retiredjg » Thu Jun 14, 2018 8:54 am

ryman554 wrote:
Thu Jun 14, 2018 8:43 am
retiredjg wrote:
Thu Jun 14, 2018 8:32 am
It would not be worth it to me. You are contemplating 4 or 5 rollovers and a roth conversion followed by a later rollover. If you are in the 25% tax bracket till the end of your days, the most you would save is $500. If you don't spend your entire IRA before you die, I guess you save nothing.
I agree with your first statement, but am a bit perplexed by the last statement. You save tax (proportionately) all the way down as, assuming no investment growth, the ratio of the basis to account balance is unchanged on form 8606 during withdrawal phase. With investment growth, I guess this ratio declines, but it's not like a step function of saving turns on at the last $2000 or so.
If the poster does the Roth conversion now, there won't be a basis any more and there won't be pro-rating with Form 8606 forever. In the 25% bracket, the tax would be $500 federal and that money will be spent now.

Without the Roth conversion, If the IRA is never all used up, that $500 would not be spent on taxes.

Maybe a little cock-eyed way to look at it, but that's how it seems to me. :D Either way, if I didn't need the $500, I would not do all those rollovers. But that's just me.

Oh, I just saw a different way to understand your post. If I decided against the rollover maneuver, I would not File the 8606 for 1987. I'd just proceed like it never happened and that no basis exists. I do not believe this is contrary to what the IRS expects of us since it does not evade any tax.

GrowthSeeker
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Re: One IRA contribution was non-deductible, but no records

Post by GrowthSeeker » Fri Jun 15, 2018 10:02 am

Thanks to everyone who has replied. My simple question wasn't so simple. The more one finds out, the more one realizes there is more to it.
My ultimate goal, at the moment, has been to minimize headaches present and especially future.
That being the case, just ignoring the IRA basis and proceeding like every IRA contribution was pre-tax is the way to go.
But the solo 401k idea sparked a new plan: tax defer my last bit of earned income. For the first few months of 2018 I had some taxable disability insurance payments. AFAIK, and I'll need my accountant to confirm, since this comes on a W-2 and was from an employer's plan, it is "earned" income. It is only about $17K, but I can put 6500 into a new Roth IRA and the rest into a solo 401k (which I would have to create). I won't have any earned income in any future years most likely.

1. Does the fact that I will get a new EIN and a new 401k mean that I have to pay the employer half of the self employment tax to Medicare and SS? ie 15.3% instead of 7.65%?
2. Am I correct that I can defer all or nearly all of this income into the combination Roth plus 401k?
2a. Is it that I can defer 100% of that income (since it's small) except for 1/2 the self employment tax which I would have to pay first???
3. Would the 401k plan have to file a form every year (I think it's called 5500)?
4. Would the 401k plan have to file a tax return every year?
5. Since I will likely do the Roth anyway, is opening a 401k just to shelter $10k not worth the bother since my total IRA sum is 800k?

Thanks for everyone's patience. But the information you're providing is helpful and hopefully educational to others as well.

Spirit Rider
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Re: One IRA contribution was non-deductible, but no records

Post by Spirit Rider » Fri Jun 15, 2018 10:44 am

GrowthSeeker wrote:
Fri Jun 15, 2018 10:02 am
It is only about $17K, but I can put 6500 into a new Roth IRA and the rest into a solo 401k (which I would have to create). I won't have any earned income in any future years most likely.
This W-2 compensation that would allow you to make a S6500 contribution and a $6500 spousal IRA contribution if applicable.

However, it is most definitely is not self-employment income. You can only make contributions to a one-participant 401k based on net self-employment earnings (business profit - 1/2 SE tax). This would only be from the $10K.
1. Does the fact that I will get a new EIN and a new 401k mean that I have to pay the employer half of the self employment tax to Medicare and SS? ie 15.3% instead of 7.65%?
A new EIN or one-participant 401k are irrelevant. If you have > $400 in business profit from self-employment, you must pay SE tax on 92.35% if your business profit. With this low an amount of total SS earnings, the SE tax will be 15.3%
2. Am I correct that I can defer all or nearly all of this income into the combination Roth plus 401k?
You can make employee elective contributions (traditional 401k deferrals or designated Roth 401 contributions) up to 100% of net self-employment earnings.
2a. Is it that I can defer 100% of that income (since it's small) except for 1/2 the self employment tax which I would have to pay first???
Yes, see above. You actually have to pay the full SE tax, but there is a deduction for 1/2 on Form 1040 line 27.
3. Would the 401k plan have to file a form every year (I think it's called 5500)?
For a one-participant 401k plan, you only have to file Form 5500-EZ when the plan's year-end balance is > $250K.
4. Would the 401k plan have to file a tax return every year?
401k plans do not file tax returns and do not pay taxes. They may have to file a version of a Form 5500 and make additional filings based on specific circumstances.
5. Since I will likely do the Roth anyway, is opening a 401k just to shelter $10k not worth the bother since my total IRA sum is 800k?
Either you save on other taxes with a traditional 401k deferral or have tax free growth with a designated Roth 401k contribution.

One caveat that may tilt the scales for Roth contributions. Tax deductible 401k contributions on Form 1040 Line 28 reduce the amount of net self-employment earnings available for the Self-Employed health Insurance Deduction on Form 1040 Line 29.

You are probably better off taking the full amount of the Self-Employed health Insurance Deduction*. You could then make that amount of Roth 401k contributions. If there is any contribution space left, your could make either 401k deferrals or Roth contributions, whichever is best for your tax/IRMAA circumstances.

* Medicare Part B and D premiums including IRMAA, Medicare Supplement premiums, etc... of you and a spouse all qualify for the Self-Employed health Insurance Deduction

GrowthSeeker
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Re: One IRA contribution was non-deductible, but no records

Post by GrowthSeeker » Fri Jun 15, 2018 12:20 pm

Ok, so what is the necessary and sufficient condition that allows W-2 income to be deferred into a solo 401k?
Is it that it be earned income?
Or is it that it be self-employment income?

I have seen that the disability income is considered "earned" if it is before the minimum retirement age. I don't have any idea what my minimum retirement age is, but the income in question ended when I was 65 years and 8 months of age, and the Social Security retirement age for my birthday is 66.

From what you have said, it sounds like the disability insurance income is "earned" but not "self-employment". With this in mind, am I even eligible to make a solo 401k?

btw, I do have traditional Medicare plus a separate Part D plan and maybe $6K of dental expenses for 2018. But if I am not considered self-employed can I still deduct some of those premiums and/or dental expenses on page 1 of the 1040 or as itemized deductions?

Spirit Rider
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Re: One IRA contribution was non-deductible, but no records

Post by Spirit Rider » Fri Jun 15, 2018 4:13 pm

GrowthSeeker wrote:
Fri Jun 15, 2018 12:20 pm
Ok, so what is the necessary and sufficient condition that allows W-2 income to be deferred into a solo 401k?
Is it that it be earned income?
Or is it that it be self-employment income?
It must be self-employment income.
I have seen that the disability income is considered "earned" if it is before the minimum retirement age. I don't have any idea what my minimum retirement age is, but the income in question ended when I was 65 years and 8 months of age, and the Social Security retirement age for my birthday is 66.
The correct term for income required to make IRA contributions is compensation. If you have W-2 box 1 wages and it is not reduced by Box 11 (NQDC) it is compensation. See IRS Publication 590-A What is Compensation.
From what you have said, it sounds like the disability insurance income is "earned" but not "self-employment". With this in mind, am I even eligible to make a solo 401k?
Not from current year self-employment which you have none. I was confused by your reference to $10K which I had assumed was from self-employment. From re-reading the entire thread, I now think it was you subtracting the $6500 IRA contribution from the disability payments.

However, Section 401(c) considers you a "self-employed individual", if you were such in any prior year. This would allow you to adopt a one-participant 401k and rollover the SEP IRA and any other IRAs. It does not allow you to make contributions based on W-2 wages.
btw, I do have traditional Medicare plus a separate Part D plan and maybe $6K of dental expenses for 2018. But if I am not considered self-employed can I still deduct some of those premiums and/or dental expenses on page 1 of the 1040 or as itemized deductions?
No, the Self-employed health insurance deduction is only available to self-employed individuals and S-Corp shareholder employees who meet requirements.

I would wait until I actually received the W-2 before I would make any IRA contributions.

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