ChainThink report: As 2026 approaches, U.S. crypto investors are poised to face a tax environment markedly different from previous years. Multiple new regulations will take effect in 2025 transactions and the 2026 tax filing season, marking what industry insiders refer to as a "watershed moment" in crypto taxation.

One core change is Form 1099-DA. Starting in 2025, U.S. centralized exchanges and other "brokers" are required to report users’ cryptocurrency sales and disposals to the IRS, with the first issuance of Form 1099-DA expected in 2026. Initial forms will mostly include gross proceeds only, without cost basis information. If taxpayers fail to clearly report their own cost basis, the IRS may default to zero cost and automatically issue a tax notice.

Meanwhile, "wallet-level cost accounting" will replace the previously widespread "pooling method" algorithm. The IRS now mandates that each exchange account or wallet must individually track cost basis, and sales must match only assets within that specific wallet’s batch. This shift has particularly significant implications for multi-exchange users, DeFi participants, and self-custody holders.

Industry tax experts note that reconstructing historical ledgers and compiling all on-chain and off-chain transaction records will become a one-time but extremely labor-intensive task. Although the IRS provided a transitional safe harbor under Notice 2024-28, the compliance window is short, and few investors have successfully completed full compliance.

Tax experts warn that without proper preparation, the 2026 tax filing season could result in "automatic triggers" due to data mismatches. Under increasingly data-driven and strict IRS oversight, proactive recordkeeping, early planning, and early engagement with tax professionals experienced in digital assets have become essential "must-do" practices for crypto investors.