Feature Article Archives - Think Outside the Tax Box

Feature Article

By Jason Dinesen, CPA

The Tips Deduction and the Self-Employed: Potholes Everywhere

By now, tax professionals and taxpayers are familiar with the fact that the One Big Beautiful Bill (OBBBA) created a new tax deduction for tips received. What we want to look at in this article is — how do self-employed taxpayers handle this deduction?

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D&A Planning After the One Big Beautiful Bill Act

After 2021, whether an expenditure was deducted currently or recovered through depreciation often affected timing, but it typically did not create a meaningful advantage from a Section 163(j) perspective. The restoration of depreciation, amortization, and depletion addbacks in the computation of adjusted taxable income (“ATI”) has changed that analysis and created a new opportunity for taxpayers with actual or anticipated interest limitation exposure. As a result, taxpayers should reconsider whether certain expenditures that historically may have been deducted immediately can instead be capitalized into depreciable or amortizable property in order to improve their Section 163(j) profile.

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Trump Accounts Are Live. Are They Spectacular?

Trump Accounts (or § 530A accounts) went live via app on July 4, 2026. According to the Treasury Department, over six million accounts have been opened. As of Monday, July 6, 2026, parents and guardians of account beneficiaries could use the app to view their children’s accounts, fund the accounts, and access balances and financial education information. The Treasury Department designated BNY Mellon “as a financial agent of the U.S. government to support implementation of the new Trump Accounts program.” BNY, in partnership with Treasury, will manage the accounts and help to develop the app taxpayers can use to manage their accounts. Robinhood Securities, LLC is acting as the initial trustee and brokerage for the accounts.

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Will AMT Make a Comeback After OBBBA?

Following Betteridge’s Law of Headlines, the answer to the question posed in the headline is, “no.” Actually — because we’re talking about taxes here — we can say the answer is never so definitive, so let’s change it to “probably not.” But it's more complicated than it may seem.

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State Tax Planning with the “80/20 Company” Exclusion

Many multinational groups find that foreign-source dividends and other income earned by domestic affiliates are fully or partially subject to state income taxation, even where the federal system provides an exemption. This state-level “leakage” can be material – particularly in high-tax jurisdictions – and is often overlooked because the income appears sheltered at the federal level. For groups with predominantly foreign operations, a starting structure or a restructuring that causes one or more domestic affiliates to qualify as an “80/20 company” can substantially reduce or eliminate state taxation on that income.

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When Your Client’s World Is Bigger Than the U.S.

A lot of client meetings still start with the same assumptions: W-2 in a U.S. state, mortgage nearby, a 401(k), maybe some RSUs, and a college-savings plan. Yet many of those “simple” clients now own an apartment in another country, freelance for a foreign company, or have parents wiring money from overseas. The tax code does not see those details as background color; it treats them as organizing facts. This is where citizenship, residency, and domicile quietly step onto center stage. For planners, the challenge is not memorizing every cross-border rule. It is knowing when a client is no longer “just domestic” and shifting your planning framework before you stumble into penalties, double taxation, or blown opportunities.

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Lessons Learned from the Tax Court: What’s at Stake?

Astute readers of this publication may recognize that I frequently write on Cryptocurrency and also on Tax Court cases. It feels like Christmas to me to be able to write about a tax court case about crypto. This is only the Third Tax court case to even mention crypto, and the first to look at the underlying principles of taxation. (The other two were about including crypto assets in a CDP hearing and a frivolous tax protester argument). Today’s case, Paschall v. Commissioner, is about the taxation of staking income.

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2026 Changes to Form 2441 and Dependent Care Benefits

The credit for dependent-care expenses (such as daycare costs) has long been stuck at 20% for "average" taxpayers. It finally gets a permanent boost in 2026 (for returns filed in 2027). Also, the amount of money a taxpayer can put into a dependent care assistance program is increasing by $2,500 for 2026. This change presents a chance for taxpayers and tax pros to reevaluate which is better – claiming the credit or using a flex plan.

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What Happens If You Can’t Use All Your Clean Energy Tax Credits This Year?

Clean energy tax credits have a lot going for them. Clients buy them at a discount, apply them dollar-for-dollar against federal tax liability, and walk away paying less to the IRS. That alone makes them worth a serious look. But here's what often gets overlooked and what makes these investments genuinely remarkable compared to almost anything else in your tax planning toolkit: the flexibility built into how and when the credits can be used. Can't absorb the full credit this year? Carry it back up to three years and trigger refunds on taxes your client already paid. Think about that for a second. There are very few places in the tax code where you can go back in time and rewrite last year's tax bill. This is one of them. Still have excess after the carryback? Carry it forward for up to 22 years. That's not a typo. Two decades of runway to put those credits to work as your client's passive income grows. And if circumstances change and the credits simply aren't needed? An emerging secondary market means there may even be an option to sell them. No other common tax planning strategy offers this combination a guaranteed discount on purchase, dollar-for-dollar offset of tax liability, the ability to look backward and forward, and a potential exit if plans change. Understanding how each of these features works is what separates a good credit investment from a great one.

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