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Tax
Tax strategies, planning, and compliance for individuals and businesses
She Claimed $3,900 in Gas on Under $40 of Receipts: What a Tax Court Loss Teaches Every Side Hustler About Recordkeeping
In Lucas v. Commissioner (T.C. Memo. 2026-22), the Tax Court disallowed ~$30,000 in Schedule C losses from an informal caregiving side hustle — gas receipts under $40 against $3,900 claimed — and upheld 20% accuracy penalties. Here's the three-factor business test, the Cohan rule's hard limits, and the recordkeeping habits that would have changed the outcome.
New Jersey's Medicaid Employer Assessment (A5324): What the First-in-the-Nation Law Means for Your Payroll
New Jersey's A5324, effective July 1, 2026, bills employers $325–$725 per year for each Medicaid-enrolled employee or dependent once 50 or more are enrolled — matched by the state, not self-reported. Here is how the tiered fees work, which workers are exempt now and in 2027, and how to prepare your books for a bill you didn't calculate.
Novak v. Commissioner: Yes, the IRS Can File a Tax Lien While Your Installment Agreement Is Pending
In Novak v. Commissioner (T.C. Memo. 2026-52), the Tax Court held the IRS may file a Notice of Federal Tax Lien while an installment agreement request is still pending — liens generally follow once a balance tops $10,000, streamlined plans end at $50,000, and taxpayers have 30 days to request a CDP hearing under IRC §6320.
You Can Lose the Hobby-Loss Case and Still Beat the Penalty
In Schumacher v. Commissioner, the Tax Court ruled an 18-year money-losing quarter horse operation a hobby under Section 183 and disallowed $191,179 in deductions — yet waived the full $33,520 accuracy-related penalty because the couple reasonably relied on their enrolled agent of 20 years. How the reasonable-cause defense works, and what side-business owners should document.
A Tax Court Judge Just Told Treasury Its Own Regulation Doesn't Count
In Siemens Medical Solutions USA, Inc. v. Commissioner (167 T.C. No. 5, 2026), the Tax Court struck down Treasury's Extraordinary Disposition Rule, restoring a full $315 million Section 245A dividends-received deduction because the regulation added conditions absent from the statute's plain text. What the ruling, decided under the post-Loper Bright standard, means for any business relying on regulatory limits that outrun the underlying law.
Sirius Solutions v. Commissioner: The Fifth Circuit Just Rewrote Self-Employment Tax for Limited Partners
On January 16, 2026, the Fifth Circuit held in Sirius Solutions v. Commissioner that "limited partner" under IRC Section 1402(a)(13) means state-law limited partner status — rejecting the IRS's functional test and exempting limited partners' distributive shares from the 15.3% SECA tax. The ruling excludes LLC members and binds only Texas, Louisiana, and Mississippi, so refund claims and clean bookkeeping both hinge on the details.
How Sports Card and Collectibles Reselling Is Taxed: The 28% Rate, Cost Basis, and the IRS's Three Buckets
Collectibles like sports cards are taxed at a maximum 28% long-term capital gains rate under IRC Section 408(m) — higher than the 15–20% most stock investors pay. Whether you owe that rate, ordinary income rates up to 37%, or can deduct grading and shipping fees depends on whether the IRS sees you as a hobbyist, investor, or dealer. Here's how the classification works, what belongs in your cost basis, and why a 1099-K doesn't change what you owe.
Suvarna v. United States: Why the Tax Refund Deadline Accepts Almost No Excuses
In Suvarna v. United States (2026), the Court of Federal Claims dismissed a $53,521 refund claim filed six months late — even though the taxpayer spent those years as his dying mother's full-time caregiver. The case explains the three-year/two-year refund deadline, why the financial disability exception rarely applies, and how business owners can catch overpayments before the clock runs out.
Tooke v. Commissioner: Why the IRS Can Say No to Your 'Reasonable' Monthly Payment
In Tooke v. Commissioner (June 2026), the Tax Court upheld the IRS's rejection of an offer in compromise that fell below the taxpayer's Reasonable Collection Potential — disallowing a speculative $85,000 medical reserve, $1,000/month in duplicative tutoring costs, and $550/month in excess transportation. What the ruling teaches about documenting household budgets for OICs and partial-pay installment agreements.
United States v. Castro: What a Tax Preparer's 188-Month Sentence Means If Someone Else Signs Your Return
The Fifth Circuit affirmed a 188-month sentence for tax preparer John Anthony Castro, whose fabricated Schedule C and Schedule A deductions caused an estimated $15.2 million tax loss across 200-plus clients. Clients remain legally liable for falsified returns — here are six checks to vet a preparer, plus how Forms 14157 and 14157-A report misconduct.
Bhutan's New 5% GST: What Small Businesses and Foreign Sellers Need to Know
On January 1, 2026, Bhutan replaced its nine-rate sales tax (0%–100%) with a flat 5% GST. Registration is mandatory above Nu 5 million (~$58,000) annual turnover — and the rules explicitly cover non-resident SaaS and digital sellers, with a 30-day registration window and a reverse-charge carve-out for verified B2B sales.
Branch v. Commissioner: Where the Cohan Rule Stops Working for Travel Deductions
In Branch v. Commissioner (2026), the Tax Court estimated rent and utilities deductions under the Cohan rule for an unfiled personal care business — but denied all travel and entertainment deductions under IRC Section 274(d), which demands strict records of date, amount, place, and business purpose that courts cannot estimate around.