Quick answer (read this first) Permitted crypto cost basis methods: FIFO (first-in, first-out) and specific identification. Both are applied at the wallet or account level under the current framework, which […]
I’m pleased to share that my co-authored article with Sulolit Mukherjee has been published in Tax Notes Federal: “Digital Asset Taxation in the United States: A Policy Analysis.” For those […]
Quick Answer: Read This First What this is: A practitioner analysis of how autonomous AI agents generate taxable events at a scale that existing tax reporting and substantiation systems were […]
Quick Answer (Read This First): The moment: Form 1099-DA issued its first reporting forms in early 2026, covering 2025 digital asset transactions. The IRS can now match independently sourced broker […]
Quick answer (read this first): The problem: Polymarket does not issue Form 1099-B, 1099-DA, or W-2G. Traders receive no standardized tax documentation summarizing their activity in order to report Polymarket […]
Quick answer (read this first): What it is: Cost basis is what was paid to acquire a digital asset, including the purchase price, expressed as a tax lot with a […]
Quick answer (read this first): The short answer: It depends and the IRS has not told you which answer applies. What the question actually means: Whether prediction market profits are […]
Quick answer (read this first): The problem: Exchange records are unavailable due to platform shutdown, lost credentials, incomplete exports, or years of unreconciled self-custody. Crypto cost basis is undocumented and […]
Quick answer (read this first): What it is: Crypto cost basis reconstruction is the process of rebuilding your digital asset transaction history at the tax-lot level by establishing what you […]
Prediction markets now operate within formal regulatory infrastructure and, in certain instances, under direct CFTC supervision. Platforms such as Kalshi function as Designated Contract Markets and list standardized event-based contracts […]
