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Crypto Aug 16, 2025 2 min read

Digital assets and the realization question.

Form 1099‑DA is arriving, the wash‑sale rules still do not apply, and most clients still do not have defensible cost basis. A short note on what changed this summer and what to do before December.

Illustration of Bitcoin, Ethereum and other crypto coins among tropical plants
Price movement isn't a tax event. Selling is.

The long‑delayed digital asset broker reporting regime is — finally — landing. For transactions on or after January 1, 2025, custodial brokers (Coinbase, Kraken, Gemini, and the rest) must issue the new Form 1099‑DA to customers and the IRS. Gross proceeds reporting applies to 2025. Basis reporting begins for assets acquired in 2026.

Broker reporting, finally

For most clients this is the first time a federal agency has been handed a clean record of their on‑exchange crypto activity. Expect the obvious consequence: automated matching letters in 2027 and beyond for anyone whose return does not reconcile to the 1099‑DA total.

What the 1099‑DA does not cover:

Cost basis is still your problem

Because 2025 is gross proceeds only, the IRS will see what you sold for but not what you paid. The burden of establishing basis sits with the taxpayer. We continue to see three failure modes:

  1. Lost exchanges. Positions acquired on platforms that have since shut down (FTX, Voyager, Celsius) often have no downloadable history.
  2. Cross‑exchange transfers. A coin bought on Coinbase, moved to a wallet, then sold on Kraken looks — to Kraken — like a zero‑basis asset.
  3. Wallet‑to‑wallet mixing. Commingled wallets make specific‑identification under Treas. Reg. §1.1012‑1(j) effectively impossible after the fact.
Starting in 2026 the safe harbor for allocating basis across wallets closes. Every wallet will need to be treated as a separate account.

No wash‑sale rule, yet

Despite repeated proposals, §1091 still does not apply to digital assets. Selling Bitcoin at a loss and rebuying it ten minutes later remains a recognized loss. This is a planning window, not a permanent state. Several 2024–2025 bills would close it; any of them could be tacked onto a larger vehicle in 2026.

What to do now

Three items for anyone holding crypto above a token amount:

If you are a high‑frequency trader, a founder with token compensation, or a fund with staking income, the 1099‑DA will not look like your internal ledger. Plan for reconciliation, not a match.

Related

We advise crypto‑native founders, funds, and individuals on basis, reporting, and entity structure.

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