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Tax-Loss Harvesting Part II: The Wash Sales Rule

At the beginning of this series, I mentioned briefly that taxpayers can use tax-loss harvesting approaches in tandem with a number of investment strategies, which we will go into in more detail in Part III. Many of these...more

Tax-Loss Harvesting Part I: Overview

What is tax-loss harvesting? “Tax-loss harvesting,” in its simplest form, is the sale of a capital asset at a loss to “mop up” tax that would otherwise be due on capital gain from the sale of another capital asset. Capital...more

Taxation of Foreign Currency Transactions Part V: Hedged Executory Contracts

What is a hedged executory contract? A “hedged executory contract” is another type of transaction that is eligible for integration under Code Section 988(d). A hedged executory contract results when a taxpayer enters into an...more

Taxation of Foreign Currency Transactions Part IV: Hedging & Section 1.988-5(a) Debt Hedges

Are there special hedging provisions for section 988 transactions? Yes. In addition to the business hedging rules I address in our earlier Q&A with Andie series, a special hedging provision is available at Code section 988(d)...more

Taxation of Foreign Currency Transactions Part III: Section 988 Transactions Defined, Character & Source

Which transactions qualify as section 988 transactions? In section 988 transactions, the taxpayer makes payments or receipts denominated in or determined by reference to one or more nonfunctional currency. ...more

Taxation of Foreign Currency Transactions Part II: Gains, Losses, Personal Transactions, and Electing Out of Section 988

Are all foreign currency gains taxable? No. Under a de minimis exemption individual taxpayers with foreign currency gains of $200 or less on a “personal transaction” do not need to report them....more

Taxation of Foreign Currency Transactions Part I: Definitions and Rules for Taxing Foreign Currencies

Navigating the federal taxation of foreign currency can be compared to trying to cross a perilous sea. Both involve unexpected rough patches, serious difficulties, and frustrating complexity....more

Business Taxation of Hedging Transactions Part V: Consolidated Groups

Do the tax hedge rules apply to consolidated tax groups? Yes. The Treasury Regulations treat members of a consolidated corporate group as divisions of a single entity. As a single entity, the risks and positions of all group...more

Business Taxation of Hedging Transactions Part III: Identification Requirements and Aggregate Hedging

When must a hedge be identified and accounted for tax purposes? Taxpayers must identity each hedging transaction and the item it hedges. A taxpayer must clearly identify a hedging transaction “before the close of the day on...more

Business Taxation of Hedging Transactions Part II: Common Situations

What is the “tax character” of a hedge? A taxpayer receives ordinary gain or loss on qualified hedges that have been properly identified in accordance with Treasury Regulation § 1.1221-2. This allows a taxpayer to ensure that...more

Business Taxation of Hedging Transactions Part I: Hedging Risks

Enterprise Risk Management is widely used in many industries and businesses. Risk managers use increasingly sophisticated approaches, methods, analytics, and frameworks to manage complex, interrelated, and interconnected...more

A Comprehensive Guide to the Deductibility of Digital Asset Losses

In November 2023, almost 11,000 cryptocurrencies and digital tokens were listed on CoinMarketCaps.com. In addition, tens of thousands of non-fungible tokens (NFTs) are sold daily on various crypto exchanges and NFT platforms....more

Hedging: Inadvertent Errors and Tax Identification

Businesses often manage their price risks by hedging those risks with financial derivative contracts. Because businesses generate ordinary income and loss on their normal business activities, they want to be sure their...more

IRS Speaks–Sort of–on NFTs and “Collectibles”

Introduction Until Notice 2023-27, the Internal Revenue Service (IRS) was silent about the tax treatment of nonfungible tokens (NFTs). When the IRS turned to NFTs, it focused on one aspect of NFTs: whether certain NFTs should...more

Taxation of Derivatives Held by Investors: What to Know

The taxation of derivatives and financial products has developed in an uncoordinated and piecemeal fashion. Tax rules have largely been enacted in response to what the government has perceived as abusive transactions —...more

Tax Return Reporting of Cryptocurrency

You need to consider how you’ll report digital asset transactions on your 2022 tax returns. Tax reporting requirements for digital assets have changed yearly since 2019, when the IRS first added a question about crypto to IRS...more

How to Donate Cryptocurrency and Other Digital Assets to Charity

Explosive growth in digital assets has left investors with real questions about how to donate cryptocurrency and non-fungible tokens. That the tax bills are high enough to generate this interest is clear evidence of the gains...more

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