Blog
Insights, analysis, and updates from the AI agent economy. Browse by tag.
Section 509(a) Public Support Test: How Nonprofits Stay Public Charities
The Section 509(a) public support test requires 501(c)(3) nonprofits to draw more than one-third of support from the public over a rolling five-year window. Fail it twice and you tip into private foundation status—facing a 1.39% excise tax on investment income, mandatory 5% annual payout, and donor deduction limits that drop from 60% to 30% of AGI.
Section 4958 Intermediate Sanctions: How Nonprofit Boards Avoid 25% and 200% Excise Taxes on Excess Benefit Transactions
Section 4958 imposes 25% and 200% excise taxes on excess benefit transactions between public charities and disqualified persons, with a 10% manager tax on knowing approvers. Following three procedural steps creates a rebuttable presumption of reasonableness that shifts the burden of proof to the IRS.
Section 461(h) Economic Performance and the Recurring Item Exception: When Accrual-Basis Liabilities Are Actually Deductible
Section 461(h) layers an economic performance test on top of the all-events test, so accrual-basis taxpayers cannot deduct a liability until the underlying activity actually happens. The recurring item exception accelerates deductions for predictable expenses when economic performance occurs within 8½ months of year-end and four specific conditions are met.
Section 382: Why Acquirers Lose a Target's Net Operating Losses
Section 382 caps how fast an acquirer can use a target's net operating losses after an ownership change — annual limit equals the loss corporation's equity value times the long-term tax-exempt rate (about 3.58% in early 2026). Here is what triggers it and the legitimate workarounds.
Section 302 Stock Redemption: How Closely-Held C Corporations Avoid Surprise Dividend Treatment
Section 302 of the Internal Revenue Code decides whether a closely-held C corporation's stock redemption is taxed as a capital sale or a full-amount dividend. This guide explains the three Section 302(b) tests, the Section 318 attribution traps that ensnare family-owned companies, the 10-year family-attribution waiver, and the partial-liquidation safe harbor under Section 302(b)(4).
Section 302 Stock Redemptions: Sale vs. Dividend Treatment in Closely-Held C Corporations
A practical guide to Section 302 stock redemptions in closely-held C corporations — when a buyback gets capital gain treatment versus dividend treatment, how Section 318 family attribution disqualifies most family redemptions, and how the four 302(b) tests plus the 302(c)(2) waiver preserve sale treatment.
The Section 199A Rental Real Estate Safe Harbor: A Guide for Schedule E Landlords
Rev. Proc. 2019-38 lets landlords claim the 20% QBI deduction if a rental enterprise logs 250+ hours of rental services a year with contemporaneous records and a signed election. Triple net leases and personal-use property are excluded.
Section 199A Rental Real Estate Safe Harbor: How Landlords Log 250 Hours, Avoid the Triple Net Lease Trap, and Lock In the 20% QBI Deduction
Revenue Procedure 2019-38 lets landlords treat rental real estate as a trade or business for the 20% QBI deduction if they log 250 hours of qualifying services, keep contemporaneous records, avoid triple net leases, and file a signed election — now permanent under the 2025 One Big Beautiful Bill Act.
Section 1248 Deemed Dividend on CFC Stock Sales: A U.S. Shareholder's Guide to E&P, GILTI, and PTEP
Section 1248 recharacterizes part of a U.S. shareholder's gain on the sale of CFC stock as a dividend, capped by the corporation's earnings and profits and reduced by PTEP from GILTI and Subpart F inclusions. This guide explains who is affected, how the lookback works, why corporate sellers can prefer the recharacterization for Section 245A, and how to build a defensible work paper.
Section 119: How Employers Give Workers Tax-Free Meals and Housing on the Business Premises
Section 119 lets employers furnish meals and lodging tax-free when they are on the business premises and for the employer's convenience — and lodging must also be a condition of employment. Qualifying value is also excluded from FICA and FUTA wages.
Section 119 Meals and Lodging for the Convenience of the Employer: How Hospitality, Hospital, and Caretaker Employers Keep On-Premises Housing and Cafeteria Meals Out of Wages
Section 119 lets employers exclude on-premises meals and required-residence lodging from employee wages, with no FICA and no income tax withholding. This guide walks through the convenience-of-the-employer test, the "more than half" safe harbor, qualified campus lodging, the Kowalski cash rule, and what the 2026 Section 274(o) deduction sunset does and does not change.
Section 105(h): The Self-Insured Health Plan Rule That Can Quietly Tax Your Best People
Section 105(h) requires self-insured health plans, including ICHRAs and HRAs, to pass an eligibility test and a benefits test each year. Fail, and a portion of a highly compensated individual's reimbursements becomes taxable W-2 income — calculated as the excess reimbursement.