Navigating Digital Asset Compliance, Enforcement and Visibility Gaps
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.
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.
In this course, 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.
Who should attend:
Tax preparers including EAs and CPAs with clients who have digital assets
2 IRS CE hours
2 CPA CPE Credits
Prerequisites: None
Program Level: Basic
Advanced Preparation: None
Field of Study: Taxes
Location: Virtual
Delivery Method: Group Internet Based
Your Instructor
Trish Turner
Tax Consultant
Trish brings more than 20 years of experience with the Internal Revenue Service, where she served most recently as the Head of Digital Assets. A recognized leader in taxation, compliance, and enforcement, Trish played a central role in shaping the IRS’s approach to cryptocurrency and digital assets. Since first engaging with crypto in 2013, she has been at the forefront of policy development, helping create much of the existing and upcoming guidance that taxpayers rely on today — including contributions to the 2014-21 Notice, the 2019 FAQs and Revenue Ruling, and other key regulatory milestones.
During her tenure at the IRS, Trish spearheaded cross-agency collaboration and international initiatives to embed digital assets into the agency’s broader compliance framework. She also helped establish the IRS’s largest whistleblower program and is widely respected for her ability to design strategies that balance innovation with accountability. Beyond government service, Trish has also worked in audit and as a professor at St. Ambrose University, her alma mater, where she enjoyed teaching and mentoring future leaders.
As a longtime advocate for crypto, Trish is excited to bring her insider perspective to the private sector with Crypto Tax Girl. She looks forward to helping clients navigate the rapidly evolving compliance landscape, better understand their regulatory obligations, and feel confident in the accuracy of their filings. At CTG, Trish will leverage her deep knowledge, extensive experience, and industry connections to strengthen the firm’s leadership in crypto tax and to build and mentor teams that can grow alongside the industry.
Outside of work, Trish loves spending time with her family. She has two daughters, a son who is currently playing college football, and a six-year-old grandson who she absolutely adores.
Next Webinar:
3/4/2026
1:00 - 3:00 pm EST
Navigating Digital Asset Compliance, Enforcement and Visibility Gaps
Boon Tax Educators is registered with the National Association of State Boards of Accountancy (NASBA) as a sponsor of continuing professional education on the National Registry of CPE Sponsors. (Sponsor ID: 170897) State boards of accountancy have final authority on the acceptance of individual courses for CPE credit. Complaints regarding registered sponsors may be submitted to the National Registry of CPE Sponsors through its web site: www.nasbaregistry.org
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