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Navigating Tokenized Securities and New 2026 IRS Reporting

As digital assets expand, tokenized securities are gaining traction among Gilbert, AZ investors and small business owners. Whether you hold tokenized real estate, corporate debt, or equity, the tax treatment remains grounded in familiar principles. However, the introduction of the new IRS Form 1099-DA starting in 2026 brings vital reporting updates that demand proactive preparation.

At Martinez & Shanken PLLC, we help our clients navigate these complex reporting shifts. Understanding the difference between the digital wrapper and the underlying investment is key to avoiding unexpected IRS audits.

Substance Over Form: How Tokenization Impacts Taxes

A tokenized security is a digital token representing ownership in a traditional asset, like stock or corporate debt. While treated as a digital asset for transfer, the IRS prioritizes economic substance over form. Tax treatment depends strictly on what the token legally represents:

  • Equity: Distributions follow standard dividend rules, and sales generate capital gains or losses.
  • Debt: Payments are treated as taxable interest income.
  • Partnership Interest: Subject to partnership tax rules, requiring Schedule K-1 reporting.

The 2026 Form 1099-DA and Broker Reporting

Beginning in 2026, brokers will report many tokenized security sales on Form 1099-DA. This form includes details like wash-sale adjustments and transaction dates, similar to Form 1099-B. However, brokers may omit cost basis data (Box 1g) for legacy acquisitions, meaning you must reconstruct your records.

Tax document tracking and tokenized securities

Some narrow exceptions exist where transactions cleared on certain regulated permissioned networks will continue to use Form 1099-B instead. Always verify which form you actually receive.

Essential Recordkeeping and Real Scenarios

Never rely solely on broker-reported forms. Keep meticulous transaction history including timestamps, purchase/sale prices, platform fees, and corporate actions. Consider these basic examples:

  • Scenario A: You buy Token A (representing stock) for $2,000 and sell it for $3,500, yielding a $1,500 capital gain.
  • Scenario B: You hold Token B (representing partnership interest), report your share of taxable income using a Schedule K-1, and adjust your basis.

Expert Digital Asset Planning in Gilbert, AZ

The IRS continues to phase in digital asset rules, and tracking updates on IRS.gov is critical. For assistance managing your tokenized investments and structuring your tax planning, contact the CPAs at Martinez & Shanken PLLC today to schedule a consultation.

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