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New tax reduction strategies carefully explained and exhaustively researched every two weeks. Receive breaking news updates on tax law changes. Members only monthly AMA with TOTTB.tax.
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FEATURED CONTENT
DeFi-nitely Confusing: Final Regulations for Digital Asset DeFi Brokers
Well, at least the treasury department is true to form. They have ruined yet another international trip for me, which is the third time if you’re keeping track at home. This time it was a weekend trip to Toronto, which coming from upstate New York is technically “international,” yet somehow substantially closer to home than New York City. Late afternoon on the Friday before New Year’s Eve, the Treasury released another 115 pages of Digital Asset Regulations, along with a 13 page notice for good measure. As we’ve discussed previously on TOTTB, the last set of regs punted on a number of more complex crypto issues. This most recent release is all about one of those issues, Decentralized Finance, better known as “DeFi.”
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CURRENT EDITION
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.
Real World Ethics: What Happens When a Judge Doesn’t Understand Tax Law
We all know how messy tax returns can get when couples who used to file jointly divorce and there are children (and tax credits) involved. It’s often difficult to explain the rules surrounding Head of Household filing status and the various tax credits available to parent-clients who have separated or divorced. But what happens when the clients misunderstand and decide to fight about it in family or divorce court? The following case study says “nothing good” can be a horrifying and frustrating answer to this question.
The Return of Taxable Student Loan Forgiveness: Planning Considerations for 2026 and Beyond
Remember the dreaded student loan “tax bomb?” For the past few years, it’s been easy to forget about it. Thanks to a temporary federal tax exclusion enacted during the pandemic, borrowers who received student loan forgiveness between 2021 and 2025 generally didn’t have to include that forgiven debt in their taxable income — leaving many borrowers (and their advisors) to wonder if the tax bomb would eventually disappear for good. Unfortunately, Congress allowed the temporary exclusion to expire. Beginning in 2026, forgiven student loan balances may once again be treated as taxable income. While that sounds like a major change, the reality is that most borrowers didn’t benefit from these tax-free years in the first place. For most borrowers, forgiveness is still years away, and there’s no crystal ball for what future federal policymakers may do. In the meantime, advisors may need to revisit planning conversations that many assumed were behind them. And depending on where a borrower lives, their federal tax bill may be only part of the story.
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