§ 1091
§ 1
Form 1099
Publication 550

Wash Sale Rules and Equity Compensation: What You Need to Know

Expert guide on wash sale rules and equity compensation: what you need to know. Covers tax implications, strategies, IRS rules, and practical examples for tech employees and expats.

3 min read

Executive Summary

Quick Answer

What is Wash Sale Rules and Equity Compensation: What You Need to Know?

[Answer based on research]

Source: IRS

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Wash Sale Rules Overview

The wash sale rule under Internal Revenue Code (IRC) § 1091 disallows a capital loss deduction if substantially identical securities are purchased within 30 days before or after the loss sale date, creating a 61-day window (30 days prior, sale day, 30 days after).[1][3][4] This rule applies to stocks, securities, contracts, options, and short sales, but not cryptocurrencies, and spans all taxpayer accounts including IRAs and spouses'.[4][5]

Key authoritative sources:

Core Mechanics from IRS Rules

Per IRC § 1091(a), no deduction is allowed for losses from securities sales if the taxpayer acquires (or has a contract/acquired right to acquire) substantially identical stock or securities within the 61-day period.[1][5] "Substantially identical" is facts-and-circumstances based (e.g., same issuer's common vs. preferred stock may qualify if economically similar; ETFs or debt securities require economic difference analysis).[6][7]

  • Timeline: 30 days before sale + sale date + 30 days after = 61 days total. Example: Sell April 15; avoid repurchases March 16–May 15.[1][3]
  • Reporting: Brokers report wash sales on Form 1099-B (same CUSIP, same account); taxpayers must track and adjust across accounts on Form 8949 and Schedule D.[4][5][9]
  • Exceptions (per Instructions for Form 1099-B): No wash sale if purchased security transfers to another account before adjustment, or certain other transfers.[9]

Disallowed loss adds to the replacement shares' basis; original holding period tacks on to new shares.[4]

Example Calculation (from multiple sources, aligned with IRS Pub. 550):


Footnotes


Primary Sources

SourceTypeURL
IRC § 1091Referencehttps://www.law.cornell.edu/uscode/text/26/1091
Treas. Reg. § 1.1091-1Referencehttps://www.law.cornell.edu/cfr/text/26/1.1091-1
IRS Publication 550 (Investment Income and Expenses)Referencehttps://www.irs.gov/publications/p550
Instructions for Form 1099-BReferencehttps://www.irs.gov/pub/irs-pdf/i1099b.pdf
Treas. Reg. §1.83-2Referencehttps://www.law.cornell.edu/cfr/text/26/1.83-2

Disclaimer: This guide discusses legal tax optimization strategies only. Tax evasion is illegal and is never recommended. This content is for educational purposes and does not constitute tax, legal, or financial advice. Tax laws vary by jurisdiction and change frequently. Always consult a qualified tax professional (CPA, tax attorney, enrolled agent) before making decisions based on this information. The authors accept no liability for actions taken based on this content.

Disclaimer

This article is for educational purposes only and discusses legal tax optimization strategies. Tax evasion is illegal and is not discussed or recommended. The information provided does not constitute tax, legal, or financial advice.

Tax laws vary by jurisdiction and change frequently. Always consult a qualified tax professional (CPA, tax attorney, or enrolled agent) before making decisions based on this content. The authors and operators of this website accept no liability for actions taken based on this information.