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Straddle and constructive sale rules

Section 1092 (straddles) defers losses on offsetting positions, and section 1259 (constructive sales) treats certain hedges of an appreciated position as a sale. Whether either reaches crypto is unsettled.

What is Straddle and constructive sale rules?

Section 1092 (straddles) defers losses on offsetting positions, and section 1259 (constructive sales) treats certain hedges of an appreciated position as a sale. Whether either reaches crypto is unsettled.

Why it matters on your return

A common hedge is holding spot BTC and shorting a BTC perpetual. Under the securities rules that can be a straddle (losses deferred) or a constructive sale (gain triggered). The statutes are written for stock, securities, and actively traded personal property; crypto plausibly qualifies as the latter, and the IRS has not said. The conservative position applies the rules; the aggressive one does not.

Example

You hold 10 BTC with a $500,000 unrealized gain and open a short perp on 10 BTC to lock in the price. Under section 1259 that may be a constructive sale recognizing the $500,000 gain now. Under the aggressive position, nothing is recognized until you actually sell.

Does the constructive sale rule apply to crypto hedges?

Unsettled. Crypto may be actively traded personal property within the statute, and a full hedge of an appreciated position is exactly what section 1259 targets. We evaluate and document the position before the hedge is placed.

Source: IRC 1092; IRC 1259; No IRS guidance as of September 2026; IRS Notice 2014-21 (property treatment)

Last reviewed September 18, 2026. Tax rules change; confirm current law before acting.

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