Proving A Timely Tax Filing

 

I admit that I am biased, but I am not a fan of filing late tax returns.

Call it Murphy’s Law:

If anything can go wrong, it will.”

I am looking at a Tax Court order. An order takes place while the case is at trial. Somebody makes a motion, the Court reviews and decides. That decision is called an order, and they are common.

The IRS filed a motion that it sent a timely Notice of Deficiency to a taxpayer.

COMMENT: A Notice of Deficiency (also called a 90-day letter, a NOD or SNOD) is the IRS determining that you owe additional tax and wanting to reduce it to assessment. Why an assessment? For one thing, the IRS (usually) has 3 years to examine and adjust your return. It has 10 years to collect an assessment. That alone is a powerful incentive.

There are rules, of course. The IRS has only so much time to send the SNOD, and you have only so much time to respond to it. In general, the IRS has three years from when you filed the return or when the return was originally due, whichever is later. There are exceptions. A key one, and one will talk about today, is if you never file a tax return.

Milton Thomas Roberts failed to file a timely return for 2014. He received a notice from the IRS in 2015 asking about it. In February 2016 he went to the post office and mailed four packages: two to the IRS and two to New York state.

COMMENT: He was filing his 2013 and 2014 taxes with the IRS and New York – hence four packages. He did so correctly: he used certified mail. Yes, it costs a few dollars, but – if you ever must prove the mailing – those are the best dollars you ever spent.

About a week later the IRS acknowledged receiving his 2013 return.

COMMENT: Having the benefit of hindsight, one wonders why the IRS did not confirm 2014. To his credit, Roberts went online and confirmed that all four packages had been delivered.

For 2016 through 2019 Robers received notices from the IRS about this tax year or that, but he never received a notice about 2014.

That changed in October 2019, when the IRS sent a notice saying it never received a 2014 return.

Roberts did not immediately respond.

In February 2020, the IRS issued a SNOD showing over $275 grand of tax due.

That caught his attention.

Roberts (re)prepared his 2014 return and sent it to the IRS on or around June 2020. It showed adjusted gross income of $587 grand and a small refund of $804.

What happened to his copy of the original 2014 sent in 2016?

No idea.

Having attracted unwanted attention, Roberts was now audited for 2014. The IRS issued a second SNOD in January 2022 for $79 grand in additional tax, along with the usual interest and penalties.

You already know they are in Tax Court. Both sides agree that Roberts filed a 2014 return. Roberts argues that he filed twice – once in 2016 and again in 2020. The IRS says: nay, nay; he filed only once and that was in June 2020.

Does it matter?

Oh, yes it does.

Remember that the IRS has three years (barring oddities) to adjust his return and assess additional taxes. Roberts asserts that he filed 2014 in February 2016. Add three years and the IRS had until February 2019 to adjust and assess.

Roberts received nothing from the IRS in 2019.

Roberts says the IRS is too late. The second SNOD is incorrect and without effect.

The IRS disagrees. They say they never received the 2014 return until June 2020. Add three years and they had until June 2023 to adjust and assess. They were easily within the window.

The IRS just filed a motion requesting the Tax Court to determine that 2014 was within the window and they had filed a correct and effective SNOD.

Judge Toro denied the motion.

Why?

There is enough doubt as to what happened. Roberts had certified mail receipts, confirmation from New York of receiving 2013 and 2014 returns, confirmation from the delivery company that all four packages had been delivered, as well as a conspicuous absence by the IRS for three ½ years concerning the 2014 tax year.

Judge Toro was not going to say that the IRS had proved their case.

Mind you, that does not mean that Roberts proved his case either.

It does mean that the case revolves on whether there was a 2014 filing in 2016.

The IRS usually has the upper hand in such matters.

But Roberts brings the receipts.

You may wonder: does the IRS sometimes lose returns?

Oh yes. They have done so with me. I remember one client specifically because it impacted a scheduled real estate closing. We resolved the matter, but it involved considerable time and stress.

I will be keeping an eye out for the resolution of the Roberts story.

My hunch: he will win.

But he is in Tax Court. He is not pro se, so he is paying for an attorney. And he will keep paying, as a motion has been decided but the case itself marches on.

Which makes me wonder: could he have avoided this by simply filing a timely tax return?

As I said, I am biased.

Our case (or motion, actually) this time is from Milton Thomas Roberts v Commissioner, Tax Court docket 7011-22.

An Intrafamily Loan, A Death And A Reportable Gift

 

Let’s talk about a (somewhat) high-end tax strategy: intrafamily loans.

At its core, it involves wealth and the transfer of wealth within a family.

Let’s walk through an example.

You want to help out your son. Your attorney or CPA mentions that one way is to loan money and charge your son as low an interest rate as possible. The fancy word for this is arbitrage, and it is how a bank makes money.

Let’s go with an easy example:

·       You loan the money at 2.45%.

·       Your son can invest in a CD at 5.45%

We are arbitraging 3 points, meaning $3 grand per $100 thousand.

Lend $1 million and you have moved $30 grand.

What is the term of the loan?

Coincide it with the term of the CD.

Let’s say 5 years.

I am seeing you move $150 grand ($30,000 times 5 years).

Then what?

He pays you back $1 million when the CD matures.

How does the IRS view intrafamily loans?

With suspicion. The IRS has multiple points of interest here.

·       Are you reporting the interest income for income tax purposes?

·       Is there a gift component to this? If so, have you filed a gift tax return?

·       If you die with the loan outstanding, is the loan properly reported and valued on the estate tax return?

·       If the loans involve grandchildren, are there generation-skipping tax considerations? If so, have you filed that return?

The IRS’ primary line of attack will be that the debt is not bona fide. How do you know if it is or isn’t? The landmark case in this area is Miller v Commissioner, and the Tax Court looked at nine factors:

·       Is there a written promissory note?

·       Is adequate interest being charged?

·       Is there security or collateral for the loan?

·       Is there a maturity date?

·       Is there a believable demand for repayment?

·       Is the loan being repaid?

·       Can the borrower repay the debt?

·       Have you created and maintained adequate records?

·       Have you properly reported the loan for tax purposes?

The closer you get to a bank loan, the better your odds of defeating an IRS challenge. There is tension in this area, as courts will tell you that an intrafamily loan does not need to rise to the underwriting level of a bank loan while simultaneously testing whether an actual loan exists by comparing it to a bank loan.

Let’s go through our CD example. What can we do to discourage an IRS challenge?

·       We can create a written promissory note.

·       We will look at the Galli case in a moment to discuss adequate interest.

·       We probably will not require collateral.

·       The loan is due when the CD matures.

·       It is not our example, but a common way to show repayment intent is to amortize the debt: think monthly payments on a house or car.

·       The loan will be repaid when the CD matures.

·       Probably. Your son never had a chance to spend the loan amount.

·       Let’s say you have good records.

·       Let’s say you use a competent tax practitioner.

Let’s review the Estate of Barbara Galli case to discuss adequate interest.

In 2013 Barbara Galli lent $2.3 million to her son Stephen. They paid attention to the Miller factors above: a written note, paying 1.01% interest and due in nine years. Stephen paid the interest reliably and Barbara reported the same as income on her tax return.

Barbara passed away in 2016.

The IRS challenged the loan for both estate and gift tax purposes. The two cases (one for gift and another for estate) were consolidated by the Tax Court for disposition.

Here is the IRS:

·       The loan was unsecured and lacked a legally enforceable right to repayment reasonably comparable to the loans made between unrelated persons in the commercial marketplace.

·       It has not been shown that the borrower had the ability or intent to repay the loan.

·       It has not been shown that the decedent had the intent to create a legally enforceable loan, or that she expected repayment.

·       The decedent did not file a gift tax return relating to the loan.

·       The estate valued the note for tax purposes at $1,624,000.

The IRS points are predictable.

Note that Barbara did not file a gift tax return. This is because she did not consider herself as having made a gift. She instead had made a loan, with interest and repayment terms. In retrospect, she should have filed a gift tax return, if only to start the statute of limitations. The return might look odd if the loan were the only item reported, as the amount of reportable gifts would be zero. It happens. I have seen gift tax returns like this.

I suspect however that it was the last factor - the difference in values - that caught the IRS’ attention. The IRS saw a loan of $2.3 million. It then saw the same loan reported on an estate tax return at $1.624 million.

Now the IRS was in Tax Court trying to explain why and how they saw a gift rather than a loan.

The amount by which the value of money lent in 2013 exceeds the fair market value of the right to repayment set forth in the note is a previously unreported and untaxed gift. 

The Court was confused. Its reading (and mine) of the above is that the IRS wanted the difference between the two numbers to be the gift and not the original $2.3 million.

How can we get to the IRS position?

The easiest way would be to charge inadequate interest. The inadequate interest over the life of the loan would be a gift.

Bad argument, however. There used to be endless contention between the IRS and taxpayers on loans and adequate interest. In some cases, the IRS saw additional compensation; in others it saw reportable gifts. In all cases, taxpayers disagreed. There was constant litigation, and Congress addressed the matter during the Reagan administration with Section 7872.

    26 U.S. Code § 7872 - Treatment of loans with below-market interest rates

              

This Section introduced the concept of minimum interest rates, which the IRS would publish monthly. Think of it as a safe harbor: as long as the loan used (at least) the published rate, Congress was removing the issue of adequate interest from the table.

Let’s look at these rates for February, 2013.

                       REV. RUL. 2013-3 TABLE 1

 

           Applicable Federal Rates (AFR) for February 2013

  _____________________________________________________________________

                                       Period for Compounding

                          _____________________________________________

  

                         Annual    Semiannual  Quarterly    Monthly

  _____________________________________________________________________

  

                              Short-term

  

      AFR                 .21%        .21%        .21%        .21%

 

                               Mid-term

  

      AFR                1.01%       1.01%       1.01%       1.01%

 

Barbara made a nine-year loan, which Section 7872 considers “mid-term.” The published rate is 1.01%.

What rate was Barbara was charging Stephen?

1.01%.

Coincidence? No, no coincidence.

 Here is the Court:

We reiterated the point later … by concluding that ‘Congress indicated that virtually all gift transactions involving the transfer of money or property would be valued using the current applicable Federal rate …. Congress displaced the traditional methodology of valuation of below-market loans by substituting a discount methodology.'

To sum up, the issue on these motions are whether the transaction was a gift, a loan, or a partial gift. We determine that the Commissioner is not asserting that the transaction was entirely a gift and would lose on the proof if he were. This leave us to apply section 7872, and under that section, this transaction was not a gift at all.”

The IRS lost. I would say that Section 7872 did its job.

Our case this time was Estate of Galli v Commissioner, Docket Nos 7003-20 and 7005-20 (March 5, 2025).