Bitcoin tax rules have continued to evolve in the United States, but the self-assessment system that underpins federal taxation has not changed — leaving Bitcoin holders responsible for identifying and reporting their own taxable events. That was the central theme of an interview with Rob Massey, who has advised on cryptocurrency tax matters at Deloitte since 2012, published by Bitcoin Magazine.

In the discussion, Massey explains why using Bitcoin as money creates “new muscle” for tax reporting, which wallet transfers are — and are not — realization events, and why 1099 forms from brokers will never present the complete picture of a taxpayer’s activity. He also shares the one thing he would ask Bitcoiners to advocate for, and it is not a repeal.

The full interview is available on YouTube.

Under IRS guidance issued in 2014, virtual currency such as Bitcoin is treated as property for U.S. federal income tax purposes, meaning that selling, exchanging, or spending it can trigger capital gains or losses that taxpayers must report themselves. Separately, the Infrastructure Investment and Jobs Act of 2021 expanded broker reporting requirements to cover digital assets, giving rise to Form 1099-DA — although, as Massey notes, such broker statements are not expected to capture the full scope of a taxpayer’s transactions. Even with those forms in the picture, transfers between a taxpayer’s own wallets involve no broker at all — one reason the self-assessment obligation continues to rest with the holder.

Among the other issues addressed in the conversation: the absence of any enacted de minimis exemption for small Bitcoin transactions, with the guidance to report everything, small or large; the questions business leaders are now asking about exchange-traded funds (ETFs), leverage, and Bitcoin lending; the taxability of everyday payments such as paying a plumber in Bitcoin; and the IRS’s visibility into activity recorded on chain. Massey also discusses what practitioners would ask the U.S. Treasury to clarify — more guidance on lending, character, and basis — as well as cross-border considerations including the lack of tax treaties covering Bitcoin, withholding, and Subpart F rules. Those outstanding requests make further Treasury guidance the item to watch as U.S. digital asset tax rules continue to evolve. The interview additionally examines how multinational companies compare Bitcoin and stablecoins across different payment corridors, how to handle long-unreported transactions such as a 2015 pizza purchase by working with an attorney and a CPA, building a complete narrative, and coming clean, and how to prove cost basis after years of moving coins between wallets.

Chapters:

• 0:00 – Where Bitcoin Tax Rules Stand: Self-Assessment and Barter Transactions
• 1:25 – Broker Reporting, 1099s and Why They’ll Never Be the Full Picture
• 2:06 – No De Minimis Exemption Has Passed: Report Everything, Small or Large
• 3:00 – What Business Leaders Ask Now: ETFs, Leverage and Bitcoin Lending
• 4:07 – Paying the Plumber Is Taxable and the IRS Sees Everything On Chain
• 5:38 – What to Ask Treasury For: More Guidance on Lending, Character and Basis
• 6:51 – Bitcoin Across Borders: No Tax Treaties, Withholding and Subpart F
• 8:50 – How Multinationals Compare Bitcoin and Stablecoins by Payment Corridor
• 10:06 – Unreported 2015 Pizza? Attorney, CPA, Complete Narrative, Come Clean
• 12:37 – Proving Cost Basis After Years of Moving Coins

DISCLAIMER: The views and opinions expressed in this show are those of the participants and do not necessarily reflect the official policy or position of BTC Inc., Bitcoin Magazine, or any affiliated entities. This content is provided for informational and educational purposes only and should not be construed as investment, legal, tax, or accounting advice. Nothing contained in this show constitutes a solicitation, recommendation, endorsement, or offer to buy or sell any securities or financial instruments. Viewers should consult their own advisors before making financial or business decisions.

This post Deloitte’s Rob Massey: What Bitcoin Investors Need to Know About The Changing IRS Tax Guidance first appeared on Bitcoin Magazine and is written by Patrick Green.