It’s been a love story for nearly three years, and now Taylor Swift and Travis Kelce may be entering their most romantic era yet: asset planning. With Swift reportedly worth $2 billion and Kelce bringing his own Super Bowl-sized fortune to the table, the question is not whether there will be champagne problems—it’s how they will sort out what stays “mine,” what becomes “ours,” and what happens if there’s a break-up.
Enter the prenup. It may not sound as swoony as an Instagram engagement post, but for a couple with music catalogs, real estate, endorsement deals, and probably several lawyers on speed dial, a prenuptial agreement is less planning for the breakup and more “you need to calm down, we handled this.” For Swift and Kelce—and, honestly, for plenty of non-billionaire couples too—the hard conversations about property, taxes, privacy, and support are often easier before the wedding than after everything has changed.
I’ll be honest: I don’t have a prenup. When I got married, I didn’t have much other than a mountain of student loan debt and dreams of becoming a tax attorney. My husband had a few more dollars in his pocket than I did, but hardly anything that we felt like we’d ever need to sort out. It all felt so simple. Years later, we have three kids, some real estate, a business, and a set of Nick and Nora glasses that we both feel pretty strongly about. It’s not so simple now.
Lance Nelson, a partner at Chester County, PA-based MacElree Harvey who practices family law, says that while previous generations might have married soon after college—when income was relatively low, and debt may have been high—the current generation is taking a page from Swift’s playbook and waiting until their careers are established before marrying. Millennials and Gen Z seem to get it. They’re entering marriage not starry-eyed but clear-eyed—less Fearless-era Swift, more Midnights. Nelson adds that these couples have something the previous generation did not: access to the internet. They know what it can look like when things can go horribly wrong and are more likely to discuss ways to protect themselves and their families in advance.
Prenups can help settle important issues like the distribution of certain assets, but they are not a substitute for thoughtful tax and estate planning—or for advice that accounts for the right jurisdiction. That’s important because family, property, and inheritance rules do not always travel neatly across borders.
For Americans abroad, tax and estate planning can come with a plot twist: the U.S. may not get the final word. In many civil law countries, forced heirship rules reserve a portion of an estate for certain family members—often children or a surviving spouse—regardless of what the decedent’s estate plan says. That can create real problems for familiar U.S. planning strategies. And because these rules may apply based on where a person lives or owns property—not just citizenship—globally mobile families should not assume that a U.S. estate plan will travel neatly across borders.
And speaking of getting the right help: AI can be a terrific tool for organizing information and helping you think through the questions to ask. But when the issue is legal advice—especially around money, marriage, taxes, estates, or confidentiality—it is not a stand-in for a lawyer.
That was the finding in a securities fraud case, in which a New York federal judge ruled that a criminal defendant’s conversations with the AI platform Claude about potential defense strategy were not protected by attorney-client privilege or the work product doctrine because the chatbot was not an attorney. Although the ruling came in a criminal case, the same reasoning would likely apply in civil matters as well—including disputes involving contracts, prenups, taxes, estates, or business issues. Asking an AI tool legal questions is not the same as speaking with counsel, and AI chats may be discoverable or used against the person who created them. You know what they say(ish): Dance like no one is watching, and use AI like your questions may one day be read aloud in a deposition.
That said, I believe AI can be incredibly useful in the tax world, and I’ll have more on that in next week’s edition.
And while we’re on the subject of tools that can be useful—but only if you understand what they can and cannot do—the Treasury Department has launched the new Trump Accounts app ahead of the program’s official July 4, 2026, debut. The app is intended to help families manage the new accounts for eligible children, but contributions cannot begin until July 4. Treasury is already warning families to watch for scams, fake websites, and improper calls or texts during the rollout. As with all of these kinds of matters, including IRS-related correspondence, if you have questions, the best plan is to head over to the official government website or app rather than clicking through links in an email or text.
And that’s it for this week’s round-up. Until next time, may your tax planning be fearless, your records be clean, and your surprises come with confetti instead of correspondence from the IRS.
Enjoy your weekend,
Kelly Phillips Erb (Senior Writer, Tax)
This is a published version of the Tax Breaks newsletter, you can sign-up to get Tax Breaks in your inbox here.
Questions
This week, a reader asks:
I recently graduated from college and got a job in another state. I thought I could deduct the cost of moving, but I don’t see anything on the IRS website. What am I missing?
Congrats on graduation and the new job—sounds like you’re entering a new era! As for the moving expenses deduction? It was changed years ago, but didn’t get as much attention as some of the other provisions under the Tax Cuts and Jobs Act (TCJA), so it’s easy to assume that it stuck around. It did not. In tax terms, this one is very much in the vault (locked away).
Under current law, the moving expenses deduction is largely unavailable to most taxpayers. For tax years beginning after 2017, moving expenses are deductible only for certain members of the Armed Forces on active duty who move pursuant to a military order and incident to a permanent change of station. Those deductible expenses generally include reasonable costs of moving household goods and personal effects, plus travel and lodging for the move, but not meals.
Before the 2017 tax law changes, the deduction was much broader. Employees and self-employed individuals could generally deduct qualifying moving expenses if the move was closely related to starting work at a new principal place of work and met the applicable distance and time tests. The deduction covered items such as transportation of household goods and travel to your new home, and it was available above the line rather than as an itemized deduction. So, a civilian taxpayer who relocated for a new job could often claim the deduction before 2018, but now you cannot do so unless the military exception applies.
Statistics, Charts, and Graphs
The Organisation for Economic Co-operation and Development (OECD) has been at the center of efforts to update international tax rules for the modern economy. Through its inclusive framework, more than 145 jurisdictions have participated in negotiations over how to address the tax challenges of digitalization, including questions about where large multinational businesses should pay tax and how to limit tax competition.
That work led to the OECD’s two-pillar project, as illustrated in the chart. As I noted, Pillar 1 aimed to reallocate some taxing rights to market jurisdictions, particularly where companies may have users or customers but little physical presence. Pillar 2, by contrast, focused on rate competition and moved further ahead, though recent discussions have raised questions about how durable that framework will be and how different national systems will coexist with it.
The broader future of international tax cooperation remains unsettled. Digital services taxes and other unilateral measures are still in place, while some countries are looking to the United Nations or other forums to address concerns they believe have not been fully resolved through the OECD process. At the same time, the discussion is still active, and the need for coordination remains significant because countries and businesses alike face uncertainty if tax rules continue to develop on a fragmented, country-by-country basis.
Taxes From A To Z: U Is For Unearned Income
Unearned income generally refers to income that is not received as compensation for performing services. Common examples include interest, dividends, capital gains, rents, taxable Social Security benefits, pension and annuity income, unemployment compensation, and many royalties. It’s especially relevant when calculating the kiddie tax or sorting estimated tax planning.
One area that can get complicated? Royalties. They’re often treated as unearned income when they are passive payments for the use of property, such as copyrights, patents, mineral rights, or other intellectual property. However, there is an important exception: royalties may be treated as earned income when they are received in the course of the taxpayer’s active trade or business. For example, royalties paid to a self-employed author, musician, artist, or inventor may be business income rather than purely unearned income if they arise from that person’s ongoing creative or commercial activity—like a certain artist who has made sure that her music catalog remains very much an active business endeavor.
Tax Trivia
The “Taylor Swift Tax” is a nickname for a levy that targets luxury vacation homes in which state?
(A) New York
(B) Pennsylvania
(C) Rhode Island
(D) Tennessee
Find the answer at the bottom of this newsletter.
Positions And Guidance
The IRS has released a new Excel-based Percentage-of-Completion Method Look-Back Interest Calculator to help businesses and tax professionals compute interest required for Form 8697 for completed long-term construction and manufacturing contracts. The calculator is intended to assist with the interest computation step, but taxpayers must still review the results carefully and ensure compliance with Section 460, the regulations, and other applicable guidance.
The IRS issued additional guidance on the applicability dates of proposed Section 892 regulations, which address when foreign governments and sovereign wealth funds may be taxed on certain U.S. investment income. The guidance provides grandfathering protection for existing investments and transitional relief before the proposed rules become final.
The IRS said it will develop an electronic system to track missing taxpayer payments after a Treasury Inspector General for Tax Administration (TIGTA) report found that the agency relies on manual spreadsheets and paper files to manage unidentified payments and payment tracer cases. TIGTA said a centralized system and program metrics would help the IRS improve oversight, consistency, and timeliness in resolving payments that cannot initially be matched to taxpayer accounts.
Noteworthy
The IRS announced that select Taxpayer Assistance Centers will be open from 9 a.m. to 4 p.m. on Saturday, May 30, to provide in-person help with tax issues, though cash payments will not be accepted.
The American Institute of CPAs (AICPA) requested that the Treasury and IRS provide guidance on proposed regulations for Trump Accounts. The AICPA’s comment letter identified several areas where additional guidance will be needed in future proposed regulations addressing contributions, distributions, and investment-related rules.
The IRS overtime increased 12% in 2025, with Taxpayer Services employees accounting for most of the additional hours as the agency dealt with workforce reductions, higher backlogs, and a prolonged government shutdown, TIGTA found. The watchdog also flagged 476 questionable overtime claims and said it plans to further review IRS controls over premium pay and mandatory overtime during the 2026 filing season.
Key Figures
That’s how much money was collected by the state of New York with the help of its Case Identification and Selection System, according to a 2012 estimate cited in a Tax Notes investigation. The system, known as CISS, is used by the New York State Department of Taxation and Finance to help process tax returns, flag returns for audit, and support collections work.
The investigation examined whether CISS could fall within the scope of New York’s 2025 law requiring state agencies to report their use of artificial intelligence (AI) systems in a publicly available database. The tax department said CISS is not an AI system, describing it instead as a tool that uses business rules and data analytics rather than machine learning or other forms of AI.
Outside experts, however, said the distinction may be less important than the system’s function. Because automated systems can influence audit selection and other taxpayer-facing decisions, they argued that tools like CISS should be subject to rigorous oversight, transparency, and independent review to help guard against errors, bias, and unfair treatment of taxpayers.
Trivia Answer
The answer is (C) Rhode Island.
The “Taylor Swift Tax” is a nickname for a levy by Rhode Island lawmakers (the Non-Owner Occupied Residential Property Act) targeting luxury vacation homes. Nicknamed after Swift’s Watch Hill estate, this measure imposes a surcharge of $2.50 per $500 of assessed value on non-primary residences worth more than $1 million that sit empty for over half the year. The surcharge on the $28 million home is estimated to add over $130,000 to her annual property tax bill alone.
Known as “Holiday House” (or “High Watch”), the 11,000 square foot waterfront mansion was originally built in the 1920s and was at one point the home of the Standard Oil heiress Rebecca Harkness. Swift purchased the historic property for $17.75 million in 2013, and the move has already paid off: it inspired Swift’s song “the last great american dynasty” on her 2020 album folklore.
Worth A Second Look
The links, clips, and tax takes readers loved (and a few you may have missed):
You can find last week’s newsletter here.
Tax Filing Deadlines
📅 June 15, 2026. Due date for your 2026 Q2 estimated tax payment.
📅 June 15, 2026. Last day for U.S. taxpayers living abroad to file without a further extension (payment was still due April 15).
Tax Conferences And Events
📅 June 2-5, 2026. National Association of Black Accountants Insight 2026: WIN (We Invest Now) Convention & Expo, Aria, Las Vegas, Nevada.
📅 June 3-6, 2026. Tax Retreat—The Anticonference. San Antonio, Texas.
📅 June 8-11, 2026. AICPA Engage. ARIA Resort & Casino, Las Vegas, Nevada, & live online.
📅 June 22-25, 2026. Latino Tax Fest. MGM Grand Hotel & Casino, Las Vegas, Nevada.
📅 July 13-15, 2026. NATP Taxposium. Huntington Convention Center, Cleveland, Ohio.
Feedback
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