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What recent tax cases teach us about planning

Cases are stories about what went wrong or right, and many repeat the same lessons: dates are strict, records matter and the role you actually play can count more than a label.

Prepared by Prem Tax and Accounting Corp. Last reviewed November 6, 2026. Figures as of November 6, 2026.

Cases are stories about what went wrong or right, and many repeat the same few lessons. Dates are strict, paper trails matter and the role you actually play in a business can count more than the label on it. We turn them into habits with the Deadline-Folder Lesson Loop. The full list of decisions is on our recent decisions page.

The short version
  • Four circuits ruled in 2025 and 2026 on the 90-day deadline to petition the Tax Court. Three allowed late filing to be excused in principle. One did not.
  • A partner's real role in running a business can matter for self-employment tax.
  • The non-willful FBAR penalty maximum is counted per report, not per account.
LessonFrom these casesWhat people in this situation often do
Treat court deadlines as firmBuller (Second Circuit, 2025), Oquendo (Sixth, 2025) and Maniktala (Eighth, 2026) allowed tolling. Kyick (First, August 17, 2026) did not and upheld dismissal.Calendar the deadline the day a notice arrives and file early. Tolling, where it exists, needs diligence and an extraordinary circumstance.
Your role can outweigh your labelK Alain, No. 24-60240 (Fifth Circuit, August 12, 2026): for self-employment tax, a limited partner is one with no significant role in managing the business.Write down who runs what, and ask us how your agreement and your actual duties fit.
Foreign account reports count by reportBittner (Supreme Court, 2023): the $10,000 non-willful maximum applies per report.List every foreign account each year and file the report on time. Willful penalties are separate.
Collection fights have a limitZuch (Supreme Court, 2025): the Tax Court case ends once the IRS drops the levy.Ask about a refund claim as its own step.

An invented example

Dev did not file his report of foreign bank accounts (FBAR) for 3 years. He had 8 foreign accounts each year, and the failure was not willful. A per-account count, which the Supreme Court rejected in Bittner, would be 3 times 8 times $10,000, or $240,000. Under its per-report rule, the most is 3 times $10,000, or $30,000. We use the $10,000 figure the Court applied. Check the current amount, because penalty figures can be adjusted.

The Deadline-Folder Lesson Loop

  • Start a folder the day any IRS or court letter arrives, with the date and the deadline on top.
  • Keep proof of every filing: mail receipts, delivery tracking and e-file confirmations.
  • Keep a list of foreign accounts and a note of who does what in the business.
  • Reread the folder at the end of each year and ask your adviser what has changed.
  • Use tracking tax changes to follow new rulings.

Common questions

Can I get extra time if I miss a Tax Court deadline?

It depends on the statute and the circuit. The Second, Sixth and Eighth Circuits allowed tolling for the 90-day deficiency deadline in 2025 and 2026 rulings. The First did not. The Tax Court still treats that deadline as jurisdictional in circuits that have not ruled. We found no Seventh Circuit ruling on it, so we treat the deadline as firm.

Does a case about a big company apply to me?

Only if the same rule and court reach you. Read [how to read tax cases](/current-topics/cases/how-to-read-tax-cases/) first.

Which K Alain opinion should I read?

The one filed August 12, 2026. A January 2026 opinion in that case was withdrawn, and the case was formerly captioned Sirius Solutions. Cite it by docket number.

Official sources

Keep reading

Questions about how the new tax law or your year-end moves apply to you? Keshav Agrawal is a U.S. CPA and a Chartered Accountant (CA) from India. We prepare U.S. and Illinois returns, plan with you, and work alongside your financial adviser, insurance agent or attorney. We sell no investment or insurance products. Book a 10-minute call or send us a message.

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