Robert W. Wood is a tax lawyer (www.WoodLLP.com) who handles tax disputes, writes tax opinions, advises on crypto, disclosures and more. He is best known for advising plaintiffs on the tax treatment of lawsuit settlements and legal fees, serves as an expert witness, and writes widely for tax publications on these and other tax topics. You can reach him or his archive of tax articles at Wood@WoodLLP.com.
IRS Waives Penalties For Reasonable Cause—Not For AI Tax Research
One of the biggest justifications for IRS penalty abatement is that a tax position was based on reasonable cause and that the taxpayer acted in good faith.
Wildfire Victims Face Major Tax Issues, Here’s A Checklist
Even without a disaster declaration, you can still make a Section 1033 election to defer your gain. But some special features will not apply.
Americans Are Leaving U.S. At Record Pace—But Not IRS Taxes
If you are a U.S. citizen, living abroad does not mean avoiding U.S. taxes. If you want to stop paying U.S. tax, you have to give up your passport or green card.
What IRS Forms Should You Sign Before Being Paid?
IRS says Form 4669 helps an employer to avoid penalties for failing to withhold taxes by showing the taxes were paid. But how can you certify that in advance?
Lawsuit Settlements Involve Tax Forms, Here’s What To Expect
If the defendant thinks they may need to issue a Form 1099, they will ask for a Form W-9. If they fail to get a signed W-9, they can withhold taxes on the payment.
California Is Pursuing Tax Cases, Some With Criminal Charges
Penalties for fraudulently registering a car out of state and claiming it is used outside California include a 50% penalty on top of the tax on the purchase price.
IRS Employment Tax Violations Can Be Criminal And Draw Prison Time
The IRS can pursue you personally if the company fails to pay the taxes. The civil penalty is 100% of the taxes not collected, and criminal liability is possible too.
How IRS Taxes Defamation Legal Settlements
Suits for damage to reputation can be about personal reputation, professional reputation or both, with legitimate opportunities for capital gain tax treatment.
Giving Back Pay Is Hard, Getting Taxes Back Is Even Harder
IRS does not allow undoing a prior transaction as if it never occurred. You cannot amend your prior year tax return to account for a later event either.
IRS Forms 1099-NEC And 1099-MISC Trigger Different Taxes
Form 1099-MISC is for miscellaneous income. But Form 1099-NEC is for payments to independent contractors and adds self-employment tax.