
Your Employee Died and You Still Owe Them a Paycheck: How Year-of-Death Wages Hit Form W-2 and 1099-MISC
Wages paid after an employee dies skip federal income tax withholding — same-year payments hit W-2 Boxes 3 and 5 plus Form 1099-MISC Box 3.
#estate-planning
Tax-efficient strategies for transferring wealth and business assets to the next generation

Wages paid after an employee dies skip federal income tax withholding — same-year payments hit W-2 Boxes 3 and 5 plus Form 1099-MISC Box 3.

A transfer-on-death deed names a beneficiary for your house the way you would for a bank account — recorded now, revocable any time, effective only at death. More than 30 states plus DC authorize one; Florida and Michigan use the Lady Bird (enhanced life estate) deed instead. Here is what each does, how to record one correctly, and the filing errors that send families back into a 9-to-18-month probate.

A March 2026 survey of about 1,000 U.S. small business owners found 40% expect to retire within a decade while 70% have no formal succession plan. Buyers price a small business on seller's discretionary earnings times a 2x–4x multiple, discounted for owner dependency, customer concentration and unreliable books. This guide lays out a six-part, three-to-five-year plan — two target numbers, three years of clean financials, operational replaceability, risk de-concentration, a deliberate exit path (third-party sale, family succession, management buyout or ESOP), and a reverse-built timeline with a CPA and attorney — plus the three mistakes that shrink exits.

Banks tied roughly $27 billion in suspicious activity to elder financial exploitation in the year ending June 2023, per FinCEN. A practical guide for business owners — the five scams draining parents' accounts, the warning signs to watch in their finances, how to get read-only visibility without starting a family fight, and the bookkeeping rules that protect you if you end up holding the power of attorney.

A business owner's guide to inventorying crypto wallets, seed phrases, and NFT holdings so your LLC's treasury survives incapacity or death — RUFADAA-compliant will language, Shamir backups, platform legacy tools, and per-wallet bookkeeping that keeps the estate honest.

Bill C-15 makes bare trust reporting mandatory in Canada for tax years ending on or after December 31, 2026, with T3 and Schedule 15 filings due March 31, 2027. Covers which small-business arrangements count as bare trusts, the narrow $50,000/three-month exemption, and penalties up to 5% of trust property value.

A Spousal Lifetime Access Trust (SLAT) lets a business owner move an appreciating asset — and all its future growth — out of the taxable estate while the beneficiary spouse retains access to distributions. With the 2026 lifetime exemption set at $15 million per individual, this guide covers the mechanics, valuation discounts, the reciprocal trust doctrine, and the divorce and death risks to plan around.

The One Big Beautiful Bill Act permanently raised the federal estate and gift tax exemption to $15 million per person ($30 million per couple) starting in 2026, eliminating the scheduled TCJA sunset to roughly $7 million. Here's what changed, which existing plans are now outdated, and the succession moves business owners should make — from portability filings to buy-sell agreement reviews and state estate tax exposure.

Split-dollar life insurance is an agreement — not a policy type — for an employer and a key employee to divide the premiums, cash value, and death benefit of one permanent policy. This guide compares the two structures (collateral assignment vs. endorsement), explains how the IRS taxes each under the economic benefit and loan regimes, why premiums are never deductible, and how to book the arrangement correctly from day one.

Alaska, Tennessee, Kentucky, Florida, and South Dakota let married couples in any state opt into community property treatment through a trust, so the entire asset — not just half — gets an IRC Section 1014(b)(6) basis step-up at the first spouse's death. What business owners should know about Section 754 elections, the one-year gift trap under Section 1014(e), and the unresolved IRS guidance.

IRS Revenue Procedure 2026-25 (June 29, 2026) creates a gift tax safe harbor for Trump Account contributions: individual donors whose total gifts to a child stay under the $19,000 annual exclusion owe no Form 709 filing, resolving the future-interest question raised by the accounts' lock-up until age 18.

IRS Chief Counsel Advice CCA 202628009 (July 10, 2026) held that a demand-based deficit restoration obligation enforceable only by withholding future distributions is not unconditional, failing both the §1.704-1(b) economic-effect safe harbor and the §1.752-2(b) recourse-liability test — a fact pattern common in family LP boilerplate that can reallocate recourse debt and suspend previously deducted losses.