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Deloitte’s Rob Massey: What Bitcoin Investors Need to Know About The Changing IRS Tax Guidance

Reported by Bitcoinmagazine
Oct 27, 2026· 2 min read
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Key Takeaways
  • • Deloitte tax adviser Rob Massey, who has advised on crypto taxes since 2012, says the U.S. Bitcoin tax system remains self-assessment, and using Bitcoin as money creates new reporting obligations for holders.
  • • Massey states that broker 1099 forms will never capture the full picture of a Bitcoin holder's taxable activity, and that no de minimis exemption has passed, so small transactions must be reported.
  • • Paying for goods with Bitcoin is a taxable event, and Massey notes the IRS can see transactions on-chain.
  • • Massey identifies lending, character and basis guidance as priority areas on which he would ask Treasury for clarification.
  • • Massey says Bitcoiners should advocate for clearer guidance rather than repeal of existing rules.
Summary
In a Bitcoin Magazine video interview, Deloitte's Rob Massey, who has advised on crypto taxes at Deloitte since 2012, outlined the current state of U.S. tax compliance for Bitcoin holders. According to Massey, while Bitcoin tax rules have evolved, the underlying self-assessment system has not changed, and the use of Bitcoin as money requires holders to build new reporting practices.

Massey addressed which wallet movements constitute realization events and which do not, and explained that Form 1099s issued by brokers will never be a complete record of a holder's taxable activity. He stated that no de minimis exemption has been enacted, so taxpayers should report transactions regardless of size. Paying for goods or services with Bitcoin is taxable, and he noted that the IRS can view transactions on-chain.

The discussion also covered questions business leaders are raising around ETFs, leverage and Bitcoin lending. Massey said he would ask Treasury for further guidance on lending, the character of gains and losses, and cost basis. He also discussed cross-border issues, including the absence of tax treaties covering Bitcoin, withholding and Subpart F considerations, and how multinationals compare Bitcoin and stablecoins by payment corridor. Proving cost basis after years of moving coins was identified as a practical challenge. Massey's recommended advocacy priority is clearer guidance rather than repeal of existing rules.

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Sources

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Bitcoinmagazine Deloitte’s Rob Massey: What Bitcoin Investors Need to Know About The Changing IRS Tax Guidance