Tax Compliance & Planning for Digital Assets

Cryptocurrency & the IRS

Tax compliance and planning for cryptocurrency transactions, mining operations, and digital-asset investments, structured for full IRS compliance and for the tax outcome you are entitled to.

Notice 2014-21 settled the doctrine: cryptocurrency is property, not currency, so every disposition is a sale with a gain or a loss measured against basis. The hard part since has been the ledger. A taxpayer with six exchanges and four wallets has a basis history in ten places, and the IRS now receives part of it directly.

Brokers began reporting gross proceeds on Form 1099-DA for sales made in 2025, and they add cost basis for covered assets acquired from 2026, so a mismatch with the return is now found by a computer. Basis has been tracked wallet by wallet since January 2025, and specific identification of the lot sold has to be made with the broker before the sale, or first-in, first-out applies. Staking rewards are income when the taxpayer can sell them, mining rewards are income at their value on the day they are mined, and the question on page one of Form 1040 is answered under penalties of perjury. We have represented clients in matters before the IRS. In those matters we represent the taxpayer, and only the taxpayer.

What we do

Cryptocurrency tax compliance and planning, from transaction reporting through audit defense.
01

Cryptocurrency Tax Compliance & Planning

Guidance on federal tax obligations for digital-asset activity, built around the IRS treatment of cryptocurrency as property and the reporting that follows.

02

Digital-Asset Transaction Reporting

Reporting for every kind of taxable event, including purchases, sales, exchanges, mining rewards, staking income, and using cryptocurrency to buy goods and services.

03

Mining-Operation Tax Strategies

Income recognition, deduction planning, and entity structuring for mining, including the income-tax and self-employment-tax questions that arise when assets are mined and held.

04

Trading & Investment Tax Optimization

Capital-gains and loss strategy for traders and investors, tracking holding periods and coordinating positions to reach the most favorable outcome the law permits.

05

IRS Audit Defense for Crypto Activities

Representation in IRS audits and examinations involving cryptocurrency transactions and digital-asset activity, supported by complete records and a defensible position.

06

Loss Harvesting & Lot Selection

Timing of sales, specific identification of lots before each trade, and loss harvesting checked against the wash-sale statute as it stands on the trade date, since Section 1031 has not applied to coin since 2018.

07

Record Keeping & Documentation

Documentation systems capturing dates, amounts, fair market values, and basis for every transaction across all exchanges and wallets, which is the foundation of accurate reporting.

08

Estate Planning with Cryptocurrency Assets

Coordinating digital-asset holdings with wealth-transfer planning, addressing valuation, basis, and the tax consequences of transferring cryptocurrency during life or at death.

What you should know

The points that shape how cryptocurrency is taxed, and where careful planning earns its keep.
01

Property since 2014

Notice 2014-21 made cryptocurrency property for federal tax purposes, so spending it is a sale, swapping one coin for another is a sale, and receiving it for services is ordinary income at fair market value. Only buying with dollars and moving coin between your own wallets are non-events, and the second has to be provable.

02

The broker now files first

Form 1099-DA reports gross proceeds for digital-asset sales made from 2025 and adds cost basis for covered assets acquired from 2026. The IRS matches those forms against Form 8949, and a return that omits a reported sale draws an automated notice. Self-custody and decentralized trades are still the taxpayer's own job to report.

03

Mining and staking are income on receipt

Mined coin is ordinary income at its fair market value on the day it is received, and that value becomes its basis. Staking rewards are income when the taxpayer gains dominion and control over them under Revenue Ruling 2023-14, even if they are never sold. A mining business pays self-employment tax as well.

04

Basis is tracked wallet by wallet

Since 1 January 2025, basis is kept by wallet or account rather than across the whole portfolio, and the lot being sold must be identified to the broker no later than the sale or first-in, first-out applies. Revenue Procedure 2024-28 gave a one-time safe harbor to allocate old unused basis among wallets before that date.

05

The statute of limitations reads the return

The IRS has three years to assess from filing, six years if the return omits more than 25 percent of gross income, and no limit where no return was filed or fraud is shown. Unreported coin gains often clear the 25 percent line, which is why open years are cured on the taxpayer's timetable.

06

Like-kind is gone; wash sales are a drafting question

Section 1031 has covered only real property since 2018, and the IRS has said earlier coin-for-coin swaps did not qualify either. Section 1091's wash-sale rule speaks of stock and securities; Congress keeps proposing to extend it to digital assets, so each loss harvest is checked against the statute as it reads that day.

07

Penalties scale with the explanation

An understatement draws a 20 percent accuracy penalty under Section 6662, fraud 75 percent under Section 6663, and an unfiled return 5 percent a month up to 25. Form 14457, the voluntary disclosure form, has had a digital-asset section since 2022, for taxpayers who would rather come in than be found.

The arc of a mandate

How this work runs

From the first wallet to the closed year.
  1. Stage 01

    Reconstruct the ledger

    We pull every exchange export, wallet address, and on-chain record into one basis history, matching lots, pricing each event at fair market value on the date it occurred, and separating the transfers that are mere movements from the ones that are dispositions.

  2. Stage 02

    Classify every event

    Each transaction is characterized as capital gain or loss, ordinary mining or staking income, gift, or non-event. Holding periods, airdrops, forks, and DeFi positions are resolved against IRS property treatment before a single form is drafted.

  3. Stage 03

    Cure the open years

    Where prior returns understate digital-asset activity, we weigh amended returns against voluntary-disclosure paths, quantify exposure by year, and file corrections on our timing, before a Form 1099 match or an examination letter forces the issue.

  4. Stage 04

    Defend and structure forward

    If the IRS examines, we answer with the reconstructed record and a defended position. Then we build the forward architecture of entity selection, loss harvesting, and transaction timing, so that next April is a formality.

The blockchain never forgets a transaction, and neither does the IRS, so your ledger has to remember first.

Yes / No
the digital-asset question every filer must answer on page one of Form 1040

Frequently asked

Common questions on cryptocurrency tax compliance before the IRS.
How does the IRS treat cryptocurrency for tax purposes?

As property, under Notice 2014-21, which the IRS has applied without change since. Every disposition is a sale: selling for dollars, swapping one coin for another, or paying for a coffee each produces a gain or loss equal to the value received less the basis of the coin given up. Coin received for services, for mining or for staking is ordinary income at its value on receipt, and that value becomes its basis. The holding period runs from acquisition, so coin held more than a year gets long-term rates. Nothing in the Code treats it as currency, which also means there is no foreign-currency exception for small personal gains.

Which cryptocurrency transactions are taxable events?

Selling coin for dollars, exchanging one coin for another, and spending coin on goods or services are all dispositions with a gain or loss. Receiving coin as pay, as a mining reward or as a staking reward is ordinary income when you control it. An airdrop following a hard fork is income when it lands in a wallet you control, under Revenue Ruling 2019-24. Buying coin with dollars, holding it and moving it between wallets you own are not taxable, but the transfer has to be documented as a transfer or the broker's form will show it as a sale.

How is cryptocurrency mining taxed?

Mining operations are subject to income tax on the fair market value of the cryptocurrency received at the time it is mined, which creates an immediate tax liability even when miners hold the newly acquired assets and sell none of them. Mining may also trigger self-employment tax obligations depending on how the activity is conducted.

What records do I need to keep for crypto taxes?

For every lot: the date acquired, the dollar value and fees at acquisition, and the same facts on disposition, kept by wallet or account because basis has been tracked that way since 2025. Keep the exchange CSV exports and the wallet addresses, since the exports stop being available when an exchange closes. If you choose specific identification, the record of the lot selected has to exist before the sale, not at filing. The retention period follows the statute of limitations, which is three years in the ordinary case and six where income was understated by more than 25 percent.

Can tax planning reduce my cryptocurrency tax burden?

Yes, within limits that have narrowed. Holding more than a year moves gain to long-term rates. Harvesting losses works because Section 1091's wash-sale rule is written for stock and securities, though Congress has proposed closing that gap more than once, so the trade is checked against current law on the day it is made. Choosing which lot to sell, identified to the broker before the sale, controls the gain recognized. Like-kind treatment under Section 1031 has been unavailable since 2018. Charitable gifts of appreciated coin held over a year avoid the gain and deduct at fair market value, with a qualified appraisal required above $5,000. An entity makes sense for a mining or trading business, not for a portfolio.

Is the IRS increasing enforcement on cryptocurrency?

The tools have changed more than the appetite. Since 2025 brokers report sales on Form 1099-DA, so unreported dispositions are caught by matching rather than by audit selection. Before that the IRS obtained customer records from major exchanges through John Doe summonses, and it still sends letters to taxpayers whose records it already holds. The Form 1040 digital-asset question, answered under penalties of perjury, converts an omission into a false statement. A taxpayer with unreported years can amend, or where the omission was willful, use the voluntary disclosure practice through IRS Criminal Investigation, but only before the IRS has started looking.

Related

Adjacent digital-asset practices that often run alongside an IRS matter.

Tax Planning for Crypto Traders

Capital-gains strategy, loss harvesting, and entity structuring for active traders, investors, and DeFi participants.

View practice →

Estate Planning & Digital Assets

Integrating cryptocurrency into wealth-transfer planning, with valuation, basis, succession, and beneficiary access.

View practice →

Regulatory Issues & Compliance

Federal and state cryptocurrency compliance, framework analysis, and the programs that keep operations defensible.

View practice →

Cryptocurrency & the SEC

Securities-law analysis for token offerings and digital-asset projects, including registration and enforcement matters.

View practice →

← Back to Digital Assets

Reviewed by Jonathan D. Herpy, Sr., Senior Partner · Last updated October 2026 · Educational overview · Not legal advice

Start a conversation

Tell us where the decision is hard.

One partner is accountable for the whole matter, and you have that partner's direct line. Chicago, London, and Dubai work to the same standard.