Educational analysis from a retired tax attorney.
Free guides, in-depth articles, and downloadable resources to navigate the new era of IRS crypto enforcement.
The Crypto Tax Threat Matrix
A free self-assessment to determine your IRS scrutiny risk and tax return exposure. Identify the gaps before the IRS does.
The Crypto Tax Threat Matrix.
The Crypto Tax Threat Matrix is a short, free self-assessment that scores your IRS scrutiny risk and surfaces the categories most likely to produce a 1099-DA mismatch or CP2000 notice. It is the simplest place to begin and pairs naturally with the articles below.
- Five-minute self-assessment, delivered to your inbox
- Identifies likely 1099-DA reporting gaps
- Highlights Ghost Basis and data decay risk
- Pairs with Tax Sentinel™ for full remediation
Learn more about the current issues surrounding the IRS.
The IRS has fundamentally changed how it monitors and enforces crypto tax compliance. Real-time exchange reporting through Form 1099-DA, AI-driven matching algorithms, and automated CP2000 notices have created a new enforcement reality. For more complex investors navigating DeFi, staking, cross-chain bridges, and multi-exchange portfolios, the stakes are even higher. These articles explore the compliance changes, the strategies available, and the documentation discipline required to stay ahead of the curve.
Navigating the Maze: The New IRS Radar System
The IRS has deployed AI matching against every crypto transaction you have ever made. Here is what that means for your filing.
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Turning Red to Green: Advanced Tax-Loss Harvesting Strategies
The wash sale rule does not currently apply to crypto — which creates a legal window most investors are not using.
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Decoding DeFi: The Wild West Goes Legit
Every DEX swap, every liquidity pool entry, every yield farm — the IRS now considers them all taxable events.
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Beyond the Basics: Data Decay and Forensic Accounting
The biggest threat to a high-net-worth crypto portfolio is not market volatility. It is data decay — and forensic reconstruction in March is too late.
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Staking and Yield: The Dominion Standard
Revenue Ruling 2023-14 settled the question. Staking rewards are ordinary income the moment you have dominion and control.
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The Surveillance Trap: IRS Audit Risks and AI-Driven Enforcement
When data is dirty, an audit can convert a paper gain into a real-world financial exposure. The IRS now pairs traditional examiners with AI tracking models.
Read ArticleFeel free to download these resources.
Reference guides and strategic assessments you can read offline and share with your CPA or tax advisor.
The Crypto Tax Threat Matrix
A strategic assessment of risk in the era of AI-driven enforcement. Enter your email to receive the free self-assessment.
Get Free AccessCPA Professional Briefing
The Crypto Audit-Ready Client Kit. Cleaner records in, safer returns out. A professional briefing for CPAs.
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