Digital assets have moved from the fringes of tax administration into the core of IRS compliance and enforcement strategy. Practitioners today face a rapidly evolving landscape in which cryptocurrency transactions, digital wallets, exchanges, and blockchain activity present both unprecedented transparency and significant visibility gaps. This course provides a practitioner-level examination of how the IRS approaches digital asset compliance, where enforcement efforts are focused, and where reporting blind spots still exist. Drawing on firsthand experience inside the IRS, Trish Turner, former Head of Digital Assets at the Internal Revenue Service and now with CryptoTaxGirl, explains how digital asset data is identified, analyzed, and used in examinations, collections, and criminal investigations. Participants will explore how the IRS obtains digital asset information, including exchange reporting, summons activity, blockchain analytics, and third-party data sources. The course also addresses common compliance failures seen in audits, the practical limitations of current reporting regimes, and how visibility gaps affect risk assessment for both taxpayers and practitioners. Emphasis is placed on practical takeaways for tax professionals advising clients with digital asset exposure, including how to identify red flags, assess compliance risk, respond to IRS inquiries, and navigate evolving reporting obligations. This course is designed to help practitioners move beyond surface-level crypto rules and understand how enforcement actually works in practice. This event may be a rebroadcast of a live event and the instructor will be available to answer your questions during the event.
Learning Objectives
After attending this presentation, you will be able to...
- Identify IRS enforcement, notice, and mismatch risks associated with Form 1099-DA and related digital asset reporting regimes.
- Apply existing federal tax law to complex digital asset transactions without reliance on product marketing or terminology.
- Determine taxpayer compliance obligations when third-party digital asset reporting is incomplete or absent.
- Evaluate basis determination risks arising from fragmented acquisition data, transfers, and wallet-level reporting limitations.
- Analyze the federal income tax treatment of digital asset losses resulting from scams, hacks, thefts, and liquidations under IRC §165 and related guidance.
- Recognize key estate and legacy planning considerations for digital assets, including custody, access, basis, and intergenerational transfer issues.
Major Topics
The major topics that will be covered in this course include:
- IRS digital asset compliance and enforcement strategy
- Cryptocurrency transactions and tax compliance
- Digital wallets, exchanges, and blockchain activity
- IRS identification and analysis of digital asset data
- Use of digital asset information in IRS examinations
- Use of digital asset information in collections
- Use of digital asset information in criminal investigations
- Exchange reporting
- IRS summons activity involving digital assets
- Blockchain analytics
- Third-party digital asset data sources
- Common digital asset compliance failures identified in audits
- Limitations of current digital asset reporting regimes
- Digital asset reporting and visibility gaps
- Taxpayer and practitioner risk assessment
- Red flags associated with digital asset activity
- Digital asset compliance risk
- Responding to IRS inquiries involving digital assets
- Evolving digital asset reporting obligations
- Practical IRS enforcement considerations for digital assets
