Number 7: Improperly Reporting Cryptocurrency Received as Earned Income

Cryptocurrency received in exchange for performing services is not taxed the same as the sale of cryptocurrency held for investment. We will explore and explain proper tax treatment of cryptocurrency as income.

Number 6Failing to Report Cryptocurrency Exchanged for Goods and Services

Thinking of paying for your new outdoor furniture from overstock.com in Bitcoin? As more and more retailers accept cryptocurrency, taxpayers need to understand the tax implications and reporting requirements associated with paying in crypto.

Number 5: Failure to Prepare and Maintain Adequate (or any!) Records Reflecting Crypto Transactions

As with any taxable sale or exchange of property, taxpayers must be able to establish basis in an asset, including cryptocurrency, in order to calculate the gain or loss and resulting tax due. Taxpayers who don’t keep good records may find themselves paying tax on the sale of crypto as if they had no basis at all in the asset. Taxpayers should resist the urge to be lulled into laziness and assume all records will be available electronically come tax time.

Number 4: Failure to Properly Calculate Cryptocurrency Gains and Losses

Did you lose money on cryptocurrency? Losses can and should be reported to the IRS just like gains, and losses may completely offset any tax consequences of gains. But if they do, taxpayers still need to report the transactions. Cryptocurrency investors are not uniquely required to only report and pay taxes on gains, and should include losses and gains when calculating tax due.

Number 3: Using Like-kind Exchanges to Report Crypto

In all fairness, this isn’t really something that I have seen any of my clients do. But because crypto held as investment is required to be reported as property, it makes sense that crypto exchanges for property, like a Tesla or exchanging Bitcoin for Ethereum should qualify for a like-kind exchange under section 1031 of the Internal Revenue Code. Unfortunately, it doesn’t.

Number 2Failure to Take Proper Steps to Pass on Your Cryptocurrency in the Event of Your Death or Disability

Do your loved ones know how to access your cryptocurrency accounts? If you die or become disabled, the value of your cryptocurrency may well be included in your taxable estate, even if your loved ones can’t actually access or unlock the value of that asset. We will explore best practices for how to ensure your loved ones are not left cleaning up your crypto mess without any access to the value of the asset.

Number 1: Failure to Report Cryptocurrency at All

By far the worst error – whether intentional or unintentional – taxpayers make when it comes to taxes and cryptocurrency is failure to report crypto transactions at all. Carolyn Schenk, the National Fraud Counsel & Assistance Division Counsel for IRS Office of Chief Counsel put it this way when addressing crypto investors who are not reporting income, “We see you.”

Putting it all Together

Since I’m not the Commissioner of the Internal Revenue Service, I don’t get to decide how the IRS is going to handle increasing and improving outreach to taxpayers who should be reporting cryptocurrency transactions on their tax returns, and I don’t get to decide how the IRS is going to bring those taxpayers into compliance. But as a tax litigator, I have a lot of ideas on how I think the IRS should be accomplishing these goals. We will finish our series with a close look at how the IRS has been handling outreach and enforcement so far, and what we’d like to see in the future.