What If The IRS Changes Mailing Addresses?

 

I am looking at case filings in the Tax Court electronic filing system.

Not mine, thankfully.

It reminds me of something.

Tax CPAs (likely) use professional preparation software. Over the years I have used several myself. Recent years have introduced the “suites,” whereby preparation software is bundled with other software (research, time and billing, practice management, yada yada). It makes it almost impossible to change, as one then has to change almost all practice software and also learn a new suite It is a monumental pain.

The preparation software has updates, of course. Sometimes I would see a prior year updating, beggaring the question: why? Why is the 2021 preparation software updating in 2025, for example?

Let talk about Boparai. As I write this, there have been 40 back-and-forth filings with the IRS, with the first one starting last spring (May 27, 2025). Rosie Boparai recently lost a motion, and this case will not go to trial.

Rosie extended her 2019 tax return from April 15, 2020 to October 15, 2020.

Rosie did not file a return, however.

Three years later (on July 17, 2023) she appeared in person at the Sacramento Taxpayer Assistance Center and attempted to hand-deliver her 2019 tax return. The TAC employees refused to accept her return, however, because she had not made an appointment.

COMMENT: I have a serious problem here. I can see if someone has a tax issue that needs research and investigation, but Rosie was just dropping off a paper return. Someone could have stamped it received and put it into the processing pipe. Is it unconventional? Yes, but so what? A taxpayer tried to comply.

Facing failure at the TAC, Rosie put the return in the mail. The return showed a refund, but she included a check for $10,000. Rosie was figuring that – sending money and simultaneously requesting a refund – someone would pay attention to her return.

NOTE: Consider the calendar here. The return was due April 15, 2020. It was extended until October 15, 2020. She put it in the mail July 17, 2023. As long as that extension was valid, Rosie is within the three-year statute of limitations for her 2019 refund.

Rosie mailed that return to San Francisco.

An average person would say she filed. A bit late, yes, but still within the rules.

Problem: the IRS closed its Fresno and San Francisco mailing addresses by the end of 2021. 

This would not have been a problem had she filed her 2019 return on time. 

The post office marked the envelope as undeliverable. Rosie asserted she never received the returned mail.

The IRS issued a NOD in February 2025.

Rosie filed a petition in Tax Court.

She also filed (or refiled, possibly) her 2019 return in May 2025.

The IRS agreed that Rosie did not owe money. The IRS however had no intention of refunding her 2019 overpayment. You know why: the return was filed outside the three-year statute of limitations.

Rosie was in Tax Court fighting to have her July 17, 2023 TAC visit/mailing to San Francisco count as filing her return.

Here is Reg 301.7502-1(c)(1):

That “properly addressed to the agency, officer, or office” language was brutal to Rosie.

A return filed in 2023 (yes, that would include a 2019 return filed in 2023) should have gone to Ogden, Utah or Cincinnati, Ohio.

Not San Francisco.

The return was not “properly addressed.”

July 17, 2023 did not count.

Which meant that Rosie had not filed her return within the three-year window. There would be no refund.

My thoughts?

The Court was right.

A lot of tax is procedural: correct form, correct date, address and so on. Rosie missed a step.

I also see Rosie being denied at the TAC as IRS negligence, impeding her attempt to comply and causing her irreparable harm.

My argument is one of equity. The Tax Court is not a court of equity, however; it is a court of law. A court of equity can … bend … the law a smidge to get to fairness. The Tax Court does not have this wiggle room. It has to follow the rules.

I expect cases like this to go away with electronic filing. Oh, I suppose there might be the oddball case here or there where the software glitches, but that should be rare.

And there is a reason why I see my preparation software updating several years after the fact.

Today we looked at the DAWSON filings for Boparai v Commissioner, Docket No. 7789-25.

Failing To Update A Plan Beneficiary Designation

 

Technically it is not a tax case, but it is so tax-adjacent it might as well be.

Let’s talk about beneficiaries on a retirement account – and, more specifically, an employer-sponsored retirement account.

Carl Kleinfeldt participated in the Packaging Corporation of America (PCA) Thrift Plan for Hourly Employees. In 2006 he designated his (then) wife – Dena Langdon – as his primary beneficiary.

Kleinfeldt and Langdon divorced in 2022. The divorce included a Qualified Domestic Relations Order (QDRO). A QDRO is a court order authorizing distribution to the nonparticipating (ex) spouse. The PCA Benefits Center distributed to Langdon as directed.

However, even after the QDRO there is one more step: has the ex-spouse been formally removed as beneficiary?

Kleinfeldt faxed a request to the Benefits Center to remove Langdon from both his health and life insurance as well as his retirement plan. The Benefits Center updated her status on the retirement account to “ex-spouse.” Mind you, this was not the same as removing her as a beneficiary altogether.

Why not?

There were written plan procedures to follow. Kleinfeldt’s fax was a good start but was not quite enough.

You can guess that Kleinfeldt died.

You know that Langdon wanted that retirement money.

You also know the matter went to court.

And we are in legal weeds immediately.

We are talking here about an employer-sponsored plan, which (almost always) makes the plan subject to ERISA.

ERISA in turn uses a “substantial compliance” doctrine when reviewing actions required under a plan document. It is what it sounds like: if you miss a minor clerical step, the law presumes that responsible parties know what was meant and are expected to act accordingly.

The Kleinfeldt Estate argued the substantial compliance doctrine with a white-knuckle grip.

The Court observed that substantial compliance has two steps:

1.  Was there intent to make the change?
2.  Was the attempt to make the change similar (in all material aspects) to the proper procedures required by the plan?

There was no argument about the first test: the fax was clear evidence that Kleinfeldt intended to remove Langdon as a beneficiary.

On to the second test.

The plan documents wanted Kleinfeldt to either (1) call the Benefits Center or (2) update his beneficiary designation online.

The plan documents nowhere stated that he could update beneficiaries by fax.

The Court did not consider this a minor clerical step.

Kleinfeldt did not follow the rules.

Meaning that Langdon won.

And fair had nothing to do with it.

Our case this time was Packaging Corporation of America Thrift Plan v Langdon, No 25-1859 (7^th Cir. Feb. 2, 2026)

New Rules for 2026 Charitable Contributions

 

I have been going through the provisions of the new tax bill (One Big Beautiful Bill Act), which I refer to as OB3 (Oh Bee Three). I like the Star Wars reverb to it.

You ever wonder how the tax Code gets so complicated?

I can understand if one is already in a complex area to begin with. Take an international conglomerate, sprinkle in some treaty relief, add transfer pricing creativity and bake off for FDDEI minutes and it makes sense.

But what about something routine – something like charitable contributions?

Let’s talk about OB3 and contributions.

We will separate our discussion into two sections: contributions for C corporations and contributions for individuals.

C Corporations

For years, the rule for C corporation contributions has been simple: there is a limit of 10% of taxable income before any charitable deduction.

EXAMPLE ONE:

Blue Sky Corp has taxable income of $1 million before a charitable deduction of $105,000. Blue Sky can deduct $100,000 ($1 million times 10%). The $5,000 balance carries forward to the next tax year.

Let’s call that 10% the ceiling. It has been tax law since I came out of school.

OB3 has introduced a floor. The new law is that C corporation contributions are allowed only to the extent they exceed 1% of taxable income before any charitable deduction.

EXAMPLE TWO:

Let’s return to Blue Sky, which made charitable contributions of $9,000. Well, 1% of $1 million is $10 grand. $9 grand is less than $10 grand, so Blue Sky gets no deduction at all.

But wait, it gets better.

There is a macabre dance between the ceiling and the floor.

·       Contributions in excess of the 10% ceiling may be carried forward.

·       Contributions cut off at the knees by the 1% floor may be carried forward, BUT ONLY IF the corporation’s contributions exceed the ceiling.

What are they talking about?

The ceiling (sub) rule has been with us for decades. In Example One, the $5,000 may be carried forward up to five years.

The floor (sub) rule is … peculiar.

Let’s go back to Example Two. Blue Sky did not clear the floor and did not exceed the ceiling. Blue Sky loses that $9 grand as a deduction forever. Blue Sky is grey.

Let’s tweak Example Two and call it EXAMPLE THREE:

Blue Sky makes contributions of $125,000.

Blue Sky loses the first 1%, which is $10 grand ($1 million times 1%).

At this point we still have $115,000 at play.

To be cut off at $100 grand, leaving $15,000.

However, since Blue Sky exceeded BOTH the ceiling (by $15 grand) and the floor, it gets to carryforward both the $15 grand (ceiling) and the $10 grand (floor) for a total carryforward of $25 grand.

Another way to say this is: if you clear both the floor and the ceiling, you are back to the old rule ($125,000 minus $100,000).

But look at the hoops you must go through to get back to where you were.

Congress has malintent, methinks.

Individuals

We also have a shiny new contribution floor for individuals. The floor is ½ of 1%, so it is less than a corporation.

The new rule for Individual contributions works solely off the floor, so we avoid the double Dutch dilemma of Example Three.  

On to EXAMPLE FOUR:

Bo Runs-Like-A-Gazelle plays in the NFL and makes $7 million.

Bo’s charitable floor is $7 million times .005 = $35 grand.

Bo makes contributions of $33,000 grand.

Bo did not clear the floor, so Bo gets no charitable deduction.

However, does Bo at least get to carryforward the $33 grand?

No, Bo does not.

Bo is hosed.

Let’s tweak for EXAMPLE FIVE:

Same as Example Four but Bo donates $50 grand.

His floor is still $35 grand.

Bo has a deduction of $15 grand.

However since Bo cleared the floor, he gets to carry over the $35 grand (the floor) to future tax years.

Bo is less hosed.

There is another grenade from OB3 that might also affect Bo: if his tax rate ever exceeds 35%, the tax benefit from a charitable contribution will stop at 35%. We will leave that tax twister for another day.

There is a positive provision in OB3 for nonitemizers: beginning in 2026 one will be able to deduct $1,000 (if single) or $2,000 (if married) for cash contributions. Yep, you will be able to claim the standard deduction and another grand (or two), assuming you made contributions. It's something.  

Congress continues to add complexity to the Code, and not just for heavy hitters like Bo. Unfortunately, these rules might (in fact, they probably will) affect you and me – average folk. So why did Congress do it?  Same reason junkies steal: Congress is addicted. There is no other reason for nonsense like this.

How will tax advisors react? We will educate clients on ceilings and floors, and we will continue to emphasize “bunching.” Bunching means that you make an oversized donation in one year and a much smaller (or no) donation the following year. It can be rough on the receiving charity (can you imagine budgeting), but what are you (as a donor) to do?