One Ex-Spouse Void the Other’s Alimony Deduction: Tax on Alimony

Assume that a divorce decree says that a payment is to be made to an ex-spouse. Does that mean that it is alimony the ex-spouse has to report as income for Federal income tax purposes?  And if not, can the ex-spouse who receives the payment request a ruling from the IRS to say that the…

Taxation of Employee Donated Sick Leave

Even simple acts of kindness, such as donating paid sick leave to co-workers in need, can trigger complex tax requirements. The IRS recently released Private Letter Ruling 200720017 that sheds light on the federal tax consequences of such donations, highlighting the importance of following specific requirements such as employer-sponsored medical leave-sharing arrangements or qualified employer-sponsored…

Aggressive State Tax Collections

If you owe back taxes, the general rule is that you pay the state and then negotiate with the IRS. The reason for this is that the states are particularly aggressive when it comes to collecting back taxes. Some states are more aggressive than others. And their practices vary over time. In the event of…

Bankruptcy Filing Does Not Prevent Innocent Spouse Relief

There are often times when different government agencies with different clients and missions are at odds with one another. This is frequently true when it comes to the IRS and the bankruptcy trustee. The IRS is tasked with protecting the government fisc. The bankruptcy trustee is tasked with protecting the estate for the benefit of…

IRS Says When a Grape is No Longer a Grape

The tax law is filled with artificial distinctions and deadlines that often don’t match up with the way businesses actually operate. One area where this is particularly true is in the realm of capitalization. Capitalization rules allow taxpayers to calendar expenses and treat them differently depending on the phase of a project or manufacturing process.…

One Ticket or Two? Withholding Tax on Small Lottery Winnings

Winning the lottery can be a dream come true for many, but it can also trigger a number of tax-related complexities. This includes everything from income tax on the sale of lottery payments to substantiating lottery costs and losses. The IRS frequently challenges these issues on audit. One of these complexities arises when it comes…

Sale of Lottery Payments: Capital or Ordinary?

The IRS is always waiting for taxpayers to have windfalls as the tax on these one-time events is significant. Lottery winnings are no exception, as they are treated as income from gambling and subject to ordinary income tax rates, which can be as high as 38% or more depending on the amount won. But what…