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Showing posts with label filing. Show all posts
Showing posts with label filing. Show all posts

Saturday, August 9, 2025

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.

Sunday, July 25, 2021

Penalties, Boyle and “Reductio Ad Absurdum.”

 

In logic there is an argument referred to as “reductio ad absurdum.” Its classic presentation is to pursue an assertion or position until it – despite one progressing logically – results in an absurd conclusion. An example would be the argument that the more sleep one gets, the healthier one is. It does not take long to get to the conclusion that someone who sleeps 24 hours a day – in a coma, perhaps – is in peak physical condition.

I am looking at a tax case that fits this description.

What sets it up is our old nemesis – the Boyle decision. Boyle hired an attorney to take care of an estate tax return. The attorney unfortunately filed the return a few months late, and the IRS came with penalties a-flying. Boyle requested penalty abatement for reasonable cause. The Court asked for the grounds constituting reasonable cause. Boyle responded:

                  I hired an ATTORNEY.”

Personally, I agree with Boyle.

The Court however did not. The Court subdivided tax practice in a Camusian manner by holding that:

·      Tax advice can constitute reasonable cause, as the advice can be wrong;

·      Relying on someone to file an extension or return for you cannot constitute reasonable cause, as even a monkey or U.S. Representative could google and find out when the filing is due.

 Here is an exercise for the tax nerd.

(1)  Go to the internet.

(2)  Tell me when a regular vanilla C corporation tax return is due.

(3)  Change the corporate year-end to June 30.

a.    When is that return due?

Yes, the due dates are different. I know because of what I do. Would you have gone to step (3) if I had not pushed you?

Jeffery Lindsay was in prison from 2013 to 2015. He gave his attorney a power of attorney over everything – bank accounts, filing taxes and so on. Lindsay requested the attorney to file and pay his taxes. The attorney assured him he was taking care of it.

He was taking care of Lindsay, all right. He was busy embezzling hundreds of thousands of dollars is what he was doing. Lindsay got wind, sued and won over $700 grand in actual damages and $1 million in punitive damages.

The IRS came in. Why? Because the last thing that the attorney cared about was filing Lindsay’s taxes, paying estimates, any of that. It turns out that Lindsay had filed nothing for years. Lindsay of course owed back taxes. He owed interest on the tax, as he did not pay on time. What stung is that the IRS wanted over $425 grand in penalties.

He did what you or I would do: request that the penalties be abated.

The Court wanted to know the grounds constituting reasonable cause.

Are you kidding me?

Lindsay pointed out the obvious:

         I was in PRISON.”

Here is the Court:

One does not have to be a tax expert to know that tax returns have fixed filing dates and that taxes must be paid when they are due.”

The Court agreed with the IRS and denied reasonable cause.

Lindsay was out hundreds of thousand of dollars in penalties.

I consider the decision the logical conclusion of Boyle. I also think it is a bad decision, and it encapsulates, highlights and magnifies the absurdity of Boyle using the logic of “reductio ad absurdum.”

Our case this time was Lindsay v United States, USDC No 4:19-CV-65.


Sunday, March 15, 2020

Can You Get Penalty Abatement If Your Accountant Dies?


What if you give your tax documents to your CPA and your CPA dies before preparing your return?

I am reading a case where that happened.

I will lead with this: the IRS assessed almost $41,000 in penalties.

The Willetts had a longstanding relationship with their CPA (Goode). In August, 2015 they gave her all the tax documents to prepare their 2014 tax return.

Time passed and the Willetts attempted to reach Goode, but without success. In October, she finally responded, explaining she had been ill and in a nursing home. She would cover any penalties and interest associated with their return.

In November, 2015 (mind you, the return was due October 15) Mrs Willett visited Goode at her home. Ms Goode assured her she would bounce back and finish their return.

That was the last time the Willetts spoke with Goode, who passed away in February, 2017.

The Willetts had some foreboding, however, as they contacted other CPA firms to address their 2014 return. There were obstacles – Goode had original documents, for example – but they were trying. The Willetts were told that the firms were already too busy with individual returns or that their return was too complex.
COMMENT: Folks, that sounds odd to this practitioner. Methinks there is more to the story.
They finally found and hired a CPA in June, 2016. They filed their 2014 return in September, 2016 – eleven months late.

You already know the IRS came back hot with penalties and interest.

The Willetts took the case to a District Court in California.
COMMENT: That means that they had to pay the penalties and then litigate for a refund. Had they gone to Tax Court, they would not have had to pay the penalties and interest before bringing suit. That would be the upside. The downside to the Tax Court is that the judges are tax specialists. It is a little harder to spin a tale to a specialist, as opposed to a district judge who is a generalist and hears a spectrum of cases.
Penalties can be abated for reasonable cause, but there is a case out there – Boyle – that greatly circumscribes a taxpayer’s ability to rely on an accountant in order to abate penalties. The Boyle decision (sort of) divided tax practice into two categories for purpose of penalty abatement:

(1) The first category is “routine” compliance, such as looking up when a tax return is due and making sure it gets filed by then.
(2) The second category includes professional advice, such as whether a Code section affects a taxpayer or what certain provisions from the 2017 Tax Cut and Jobs Act even mean.

The Boyle court acknowledged that one could rely on an accountant for column two issues, but one probably could not rely for purposes of column one.  The IRS has subsequently interpreted Boyle aggressively, arguing that the qualifier “probably” is not even required in the preceding sentence.

So how does Boyle work when your CPA dies? Is it more like column one or more like column two?

The Court discussed issues surrounding taxpayer reliance on an agent, but at heart the Court was looking at someone who relied on an accountant – apparently a sole practitioner – who was quite ill, in and out of nursing facilities and incapable of producing timely work.

Question: what would a reasonable person do?

After all, the concept is reasonable cause.

The Court was not at all persuaded that reasonable people would wait endlessly for their accountant to recover from a nursing home stay before preparing their return. A reasonable person would seek-out another accountant – even if it was a one-off engagement - in order to meet their tax responsibilities.

There was no reasonable cause.

I admire the Willetts’ loyalty to their practitioner, but their delay cost them $41 grand.


Friday, August 26, 2016

What Does It Take To Get Reasonable Cause Around Here?



My partner has a difficult IRS penalty issue.

He expects a client to be penalized for more than one year. This complicates how we handle the first year.


The IRS has reorganized its penalty review function to a system called the Reasonable Cause Assistant (RCA). There however is a problem: the system does not work well. The Treasury Inspector General for Tax Administration (TIGTA) reported that RCA was inaccurate 89% of the time in 2012.

Step away from RCA and you still have the following:
 * It used to be that penalties were assessed as a means to encourage voluntary compliance. Many tax pros feel that is no longer the case, and penalties are being used as a means to raise revenue.  An example is the penalty assessed for late filing of a partnership return: $195 per month per partner. Take a 10-person partnership, file a week late and face a $1,950 penalty. There is little consideration for the size of the partnership, its total assets or revenues - or the fact that partnerships do not pay federal taxes.            
* Penalties are assessed even when taxpayers are trying to do the right thing. For example, enter into a reportable transaction, disclose it on your tax return but forget to file a copy with a second office and you will be assessed a penalty. Fail to disclose the transaction at all and you will be subject to the same penalty.
 * The IRS is automatically asserting penalties. For example, for fiscal year 2015, the IRS assessed over 40 million penalties on individuals and businesses. To put that in context, there were approximately 243 million returns filed for the period.
* Many penalties can be waived if the taxpayer can show "reasonable cause," but many tax professionals believe the IRS has so narrowed the definition as to be almost unreachable, unless you are willing to die. To aggravate the matter, the IRS has also instructed its personnel to substitute "first time abatement" (FTA) for reasonable cause as a matter of policy. While the IRS argues that FTA is easier to review and administer than reasonable cause, there exists a high degree of skepticism. Why would a taxpayer automatically burn a "get out of penalty-jail free" card if the taxpayer otherwise has reasonable cause? Wouldn't a taxpayer want to keep that card available just in case?
My partner - by the way - has that last situation: burning his FTA chip without a reasonable-cause backup for the second year. Ironically, he may have reasonable cause for the first year, but that sequence does not follow IRS policy. I anticipate going to Appeals to obtain reasonable cause and preserve the FTA for the second year.

Let's talk about the Carolyn Rogers (Rogers v Commissioner) case.

Carolyn lived in New York. In 2006 she had a small business (Talk of the Town Singles) which she operated from her cooperative. In 2006 there was a fire which rendered the place uninhabitable.

She moved. In 2007 there was another fire, one she appears to have caused herself. The local newspaper called her out, and she was thereafter harassed by people in her neighborhood.

She moved to the YWCA until 2010. She did not have a pleasant time there, and in 2009 she fell off a subway platform and fractured her skull on the rails. She was in the hospital for days, and she continued to suffer from dizzy spells thereafter.

Prior to this period, she had a record of filing timely returns. She also made significant efforts to correctly prepare her tax returns, consulting books and references and more than once contacting the IRS. She did not use a paid preparer.

The IRS penalized her for not filing a 2009 return.

She explained that the insurance company settled the second fire in 2009, and she lost a bundle. According to her research, the casualty loss would wipe out her income, and she was therefore below the filing threshold. She did not need to file.

The IRS then trotted technical guidance on a casualty loss. While the layperson might think that the loss would be deferred until the insurance is settled, the tax Code uses a different test:
* If an insurance claim is not paid in the year of casualty AND there is a reasonable prospect of recovery, then the loss is deferred until one can determine the amount of recovery.
* If there is no hope for insurance - or the prospect of recovery is unreasonable - then the loss is deductible in the year of the casualty.
 The IRS said that she came under the second rule. She knew that insurance would not cover the full loss from the 2007 fire. The loss was therefore deductible in 2007.
COMMENT: There is enough "what if" to this rule that even a tax professional could blow it.
The IRS wanted penalties for not filing that 2009 return.  

The Tax Court reviewed her filing history and her chaotic life. It noted:
Petitioner's error (regarding the proper year of deduction of the portion of a casualty loss for which there is no reasonable prospect of recovery from insurance) is considerably different from the errors made by a taxpayer whose failure to file, late filing, or late payment is chronic. Erroneously deducting a loss in a year later than the correct year is not usually considered to be a blatant tax avoidance technique ..."
Ouch. The Court did not appreciate the IRS wasting its time.
Taking into account all of the facts and circumstances, we conclude that petitioner exercised ordinary business care and prudence under the difficult circumstances in which she was living at the time leading up to the due date of her 2009 return...."
The Court found reasonable cause. She owed the tax, but she did not owe the penalties.

The IRS should have found reasonable cause too. It is troubling that it didn't.

Friday, August 29, 2014

What Happens When Hacking Concerns Conflict With A State Electronic Payment Mandate?



Let’s travel to the Bay State for a taxpayer requesting reasonable cause against the imposition of penalties.  

The amount in dispute is $100.

Yes, you read that correctly.

Our protagonist is Jonathan Haar, and he lives in Massachusetts. On April 15, 2011 he had the audacity to file a paper extension and include a $19,517 check for his tax year 2010 state return. The paper extension and payment

“… did not comply with the requirements set forth in Technical Information Release (“TIR”) 04-30 (“TIR 04-30”), which states that if a payment accompanying an extension application equals $5,000 or more, such extension application and payment must be submitted electronically.”

Got it. The state says that it is less expensive to process electronic than paper tax filings and payments. Seems reasonable. How do we get people to follow along, however? One way is to make whatever the state wants mandatory.

Our protagonist unfortunately had travelled this path before, and he had been warned for tax year 2005 and penalized for year 2006.  Massachusetts had a tax recidivist! They assessed the above-mentioned $100 penalty on our ne-er-do-well.


If you were my client, I would have told you to pay the $100 and move on. Mr. Haar is not my client, and he refused to pay. He instead filed an appeal, which appeal went to the Massachusetts Appellate Tax Board.

His argument?

“Mr. Haar maintained that the Commissioner’s electronic payment mandate is a ‘serious invasion of both [his] privacy and [his] personal business practices,’ as it exposes his finances to risk of cyber attack.”

 “I intentionally do no electronic banking nor direct bill paying, I have none of my credit cards linked to my bank accounts directly and I think anyone who does any of the above is exposing themselves to multiple risks of cybercrime and identity theft.”

Mr. Haar further expressed doubts as to the security of the computer systems used by the Department of Revenue (“DOR”), noting that "if the Pentagon can be hacked," he had little confidence that DOR could protect his – or anyone’s – personal data from theft.

Massachusetts argued that it had the authority to mandate electronic filing and payment, as well as assess penalties if a taxpayer failed to comply with their filing and payment mandates. Massachusetts does recognize exceptions for reasonable cause, but its own Administrative Procedure 633 (“AP 633”) provides that

… the fact that a taxpayer does not own a computer or is uncomfortable with electronic data or funds transfer will not support a claim for reasonable cause.”

COMMENT: Call me quaint, but I would say that someone not having a computer is prima facie reasonable cause for not being able to file an electronic return or transfer funds electronically. The issue I see with AP 633 is its absolutism: the language “will not support” leaves no room. Why not say instead “generally will not support,” if only to allow space for unexpected fact patterns? 

In support of its position, the DOR trotted out two officials: the first was Robert Allard, a tax auditor. He pointed out that Mr. Haar filed an electronic return, presumably through a professional preparer. I suppose that Mr. Allard felt that if one could electronically file then one should be able to electronically pay. 

The second was Theresa O’Brien-Horan, a 26-year employee and Deputy Commissioner, who testified that

… the mandate at issue in this appeal – requiring individual taxpayers who apply for an extension with an accompanying payment of $5,000 or more to file and pay electronically – is helpful to DOR because it maximized up-front revenue intake.”

… the $5,000 threshold was chosen because it would ‘impact 17% of the taxpayers, but … get the money banked for 84% of the revenue.”

You can virtually feel the customer service vapor emanating from Ms O’Brien- Horan.

When asked whether reasonable cause was the Massachusetts equivalent of an ”opt out,” Ms. O’Brien-Horan answered “yes.”

OBSERVATION: The IRS, for example, prefers that one file an electronic return. The IRS however did not put the burden on the taxpayer; rather it put the burden on the preparer. If a preparer prepares more than a minimal number of returns annually, the preparer is required to file the returns electronically. This is awkward, as the return belongs to the taxpayer and not to the preparer. The preparer is not allowed to release any return – even to the IRS – without the taxpayer’s approval. What does the preparer do if the taxpayer does not grant approval? The preparer includes yet-another-form with the return indicating that the taxpayer has “opted out.” This prevents the IRS from penalizing the preparer for not filing electronically.

If Mr. Haar’s position was reasonable, then Mr. Haar could “opt out,” irrespective of any self-serving Massachusetts Administrative Procedure.

Ms. O’Brien-Horan just didn’t think that Mr. Haar was being reasonable.

But the Board did.

“Given his reference to the hacking of the Pentagon’s computer system, and in light of the many well-publicized instances of large-scale thefts of financial information following computer breaches at businesses and other institutions, and the appellant’s consistent practice of avoiding electronic payment of all his bills, including his tax obligations, the Board found that the appellant’s failure to utilize the Commissioner’s mandated electronic tax payment to be reasonable.”

Two things strike me immediately.

The first is the cause for concern comprising Mr. Haar’s argument. It had not occurred to me to off-grid all of one’s banking transactions, but he gives one pause. I recently read the following on www.marketwatch.com, for example:

A Russian gang has stolen 1.2 billion user names and their passwords as well as more than 500 million email addresses, the New York Times reports.

The information came from more than 400,000 websites, according to the Times, which says researchers at Milwaukee-based Hold Security discovered the cyber heist.

Mr. Haar is highly cautious. His position is somewhat eccentric but not unfounded. A reasonable tax collection agency would have granted him this one and moved on.  

The second is the inanity of Massachusetts DOR. Rather than abate a $100 penalty, it preferred to pursue the matter, at who knows what cost to state and citizens. We know that cost would include Mr. Allard and Ms O’Brien-Horan’s payroll, not to mention that of their superiors, legal counsel and who-knows-what else. I can understand not wanting to set a precedent, but … really? My take is that the DOR is too well-funded if they have the time and money to pursue nonsense like this. Perhaps DOR budgets cutbacks are in order for Massachusetts.