What Is the “Constructive Sale” Rule and How Might It Affect Options?

The constructive sale rule prevents a taxpayer from locking in a gain on an appreciated position while deferring tax by entering into an offsetting position. Entering into certain option strategies, such as a short sale against the box or a collar, can be deemed a "constructive sale," forcing the recognition of the gain in the current tax year.

How Does the Time-to-Settlement Affect the Volatility Caused by Margin Calls?
How Does a Change in Capital Gains Tax Affect a Derivative’s Profitability?
What Is the Current Maximum Long-Term Capital Gains Tax Rate?
What Is the Maximum Long-Term Capital Gains Tax Rate Currently?
When Might a Trader Prefer the Specific Identification Method over FIFO?
What Is the Tax Implication If a Crypto Option Is Classified as a “Collectible”?
How Do Perpetual Contracts Allow Traders to Avoid Capital Gains Tax on the Underlying Asset?
What Is the Significance of the “Constructive Sale” Rule in Section 1256 Taxation?

Glossar