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This week’s free Tax Breaks newsletter is out.I started with the World Cup because, despite the complaints about ticket ...
06/16/2026

This week’s free Tax Breaks newsletter is out.

I started with the World Cup because, despite the complaints about ticket prices, travel, logistics, heat, commercialization, and everything else, the tournament still feels a little magical.

And because this is me, that somehow turned into a tax story.

With the U.S. hosting 78 matches in 11 cities, the World Cup is not just a sporting event. It is also a cross-border tax moment, involving money, work, players, coaches, referees, sponsors, and host-city economics.

Also in this week’s issue:
• Can you deduct an AI subscription if you use it for tax prep?
• Why SpaceX’s expected IPO could create a tax windfall for California
• What a withholding agent is, and why the role matters
• Curaçao tax trivia, in honor of its historic World Cup qualification
• IRS Security Summit updates
• June 2026 applicable federal rates
• IRS/ICE data-sharing concerns flagged by TIGTA
• Upcoming tax deadlines and events

And yes, the newsletter is free.

Read and subscribe here:

Plus: Writing off your AI subscriptions, SpaceX’s IPO and taxes, withholding agents, IRS exchanges info with ICE, tax trivia and more

A federal judge in Massachusetts has blocked the Trump administration’s $100,000 H-1B fee.That matters for employers, un...
06/11/2026

A federal judge in Massachusetts has blocked the Trump administration’s $100,000 H-1B fee.

That matters for employers, universities, hospitals, and foreign workers. But it also matters for another reason: this is the latest reminder that tax is becoming one of the courts’ favorite ways to talk about power.

The H-1B program allows U.S. employers to sponsor foreign workers for temporary employment in “specialty occupations.” We tend to associate H-1B visas with tech jobs, but the program also includes medicine, education, engineering, science, and other specialized fields.

The administration framed the $100,000 payment as an immigration restriction aimed at curbing abuse and protecting American workers. But Judge Leo T. Sorokin saw the payment differently. He concluded that it functioned as a tax.

That matters because Congress has the constitutional power to tax. The President does not have independent taxing authority.

So the case is not just about whether the President has broad immigration power. The more precise question is whether that power includes the authority to impose a massive payment requirement on participation in a lawful statutory program.
The court said no.

That reasoning fits into a broader pattern. In the Affordable Care Act case, NFIB v. Sebelius, the Supreme Court said a payment could be treated as a tax based on what it does (here, it's a revenue raiser).

The case is likely not over. An appeal seems likely, and the fight may eventually reach the Supreme Court.

I always say: Tax touches everything.

More here:

A federal court blocked Trump’s H-1B fee, but the bigger fight is about whether the President can use broad immigration authority to impose what looks like a tax.

06/11/2026

The 2025 IRS Data Book is out, and I’ve been digging into the numbers this week.

Another number that stands out? In fiscal year 2025, the IRS processed 271.4 million federal tax returns and supplemental documents, and more than 224.2 million returns and forms were filed electronically.

That’s a useful reminder that e-filing is the dominant filing method, but also that not everything can be e-filed.

Paper may be the IRS’s kryptonite, but we’re not ready to throw it all out yet.

06/10/2026

The 2025 IRS Data Book is out!

Everyone loves a good refund stat, so here you go: In fiscal year 2025, the IRS issued 116.9 million individual income tax refunds totaling $516.4 billion.

At Tax Retreat, National Taxpayer Advocate Erin Collins offered a candid look at what is happening inside the Taxpayer A...
06/07/2026

At Tax Retreat, National Taxpayer Advocate Erin Collins offered a candid look at what is happening inside the Taxpayer Advocate Service—and why it matters for taxpayers and practitioners.

TAS is often described as the “voice of the taxpayer” inside the IRS. It helps individual taxpayers and businesses resolve serious IRS problems when regular channels are not working. But it also has a broader mission: identifying systemic problems and recommending changes to improve tax administration.

Right now, TAS is under pressure.

Collins said case inventory is climbing, while TAS has lost roughly a quarter of its case advocates. That means fewer experienced employees are handling more complicated cases—often involving refund delays, identity theft, collection issues, unclear notices, financial hardship, or taxpayers who have already tried and failed to get answers from the IRS.

Still, Collins pointed to progress. TAS has pushed for clearer math-error notices, taxpayer-service legislation, and reforms that could make it easier for taxpayers to understand and exercise their rights.

She also urged tax professionals to report recurring IRS problems through SAMS, TAS’s Systemic Advocacy Management System. Practitioners often spot patterns before policymakers do.

The bigger message: tax administration is not just about processing returns or collecting revenue. It is about maintaining public trust in a system that depends on voluntary compliance.
Most taxpayers are trying to do the right thing. The system has to give them a fair chance to do it.

More here:

National Taxpayer Advocate Erin Collins talked IRS strain, taxpayer rights, legislative reforms and the importance of fairness in voluntary compliance at a tax conference.

I read a post on another site that was filled with advice on how to act at a conference.Yay, I guess? Maybe some folks f...
06/06/2026

I read a post on another site that was filled with advice on how to act at a conference.

Yay, I guess? Maybe some folks find that useful, but I find it stressful.

Here's my tip: Be yourself. It's a chance to meet people and learn new things, not an audition.

And before you assume that I'm being breezy or whatever because I attend a lot of these kinds of events, let me set the record straight: I'm a homebody. I'm happiest with coffee and my kids. I'm very unrehearsed. I forget names. I will say the wrong thing. It is not unlikely that I will trip over something, including my own feet.

And I keep going back.

Because there are so many wonderful people to meet and so many amazing places to see. Don't be intimidated or worry that you're doing it wrong, no matter what you see on the socials.

I'm reminded of this quote which, as it turns out, isn't really from Mark Twain at all, but it sums up how I feel about these sort of things: Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.

So, if you're on the fence this year about getting out there and saying hello to your peers, don't be.

Despite what it looks like, we're all in the same boat.

The IRS is holding hiring events across the country through July for seasonal roles, including customer service represen...
06/05/2026

The IRS is holding hiring events across the country through July for seasonal roles, including customer service representatives and tax examining technicians. 🧾

These are entry-level positions, and prior tax experience is not required. New hires will receive training.

The IRS recommends applying through the USAJOBS announcement before attending. Qualified attendees who apply in advance may receive on-the-spot job offers at the events.

Good opp for folks interested in public service, taxpayer assistance, and benefits. 💼

The IRS is hiring mission-critical, entry-level customer service positions in 8 locations. These roles offer a unique, non-repetitive workday that showcase your verbal and written communication skills while offering rewarding public service opportunities.

Gas prices have come down from where they were a few weeks ago, but they remain much higher than last summer—and that’s ...
06/05/2026

Gas prices have come down from where they were a few weeks ago, but they remain much higher than last summer—and that’s sharpening the debate over gas taxes.
For drivers, the concern is straightforward: what it costs to fill up.
For lawmakers, it is more complicated. Temporarily suspending the federal gas tax could offer some short-term relief, but it would also reduce revenue for the Highway Trust Fund, which helps pay for roads, bridges, transit, and other transportation projects.
That fund is already under pressure. The federal gas tax has remained at 18.4 cents per gallon since 1993, is not indexed for inflation, and brings in less relative revenue as vehicles become more fuel-efficient or fully electric.
So while a gas tax holiday may sound simple, the tradeoff is not. The policy question is how to help drivers now without making it harder to maintain the roads and bridges everyone relies on later.
More here:

With pump prices still well above last year’s levels, lawmakers are again weighing a temporary gas-tax cut. But the Highway Trust Fund is already under strain.

06/05/2026

Treasury has launched the official Trump Accounts app ahead of the program’s July 4, 2026, debut.

A few key takeaways:

• Activation emails will be sent in phases.

• Legitimate activation emails should come only from [email protected].

• Treasury says it will not contact families by phone or text to activate an account.

• Contributions cannot begin until July 4, 2026.

• The $1,000 federal pilot contribution is not automatic—you must make the required election.

• There is no cost to open a Trump Account.

The big caution here is scams. New federal programs almost always create opportunities for lookalike websites, fake customer service numbers, and “helpful” third parties to request personal information or payment.

Use only the official app or type TrumpAccounts.gov directly into your browser.

I break down what families need to know here: https://www.forbes.com/sites/kellyphillipserb/2026/05/29/treasury-launches-trump-accounts-app-as-funding-date-approaches/

Popped up in my feed.I still believe this. Did I love spending money on school? Nope.Do I regret it? Also nope.
06/05/2026

Popped up in my feed.
I still believe this.
Did I love spending money on school? Nope.
Do I regret it? Also nope.

Ben Stein, Kelly Phillips Erb, Ramit Sethi and other money gurus re...

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