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Tax Strategy: Developments in the taxation of digital assets

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The taxation of digital assets continues to be an area of confusion. The Internal Revenue Service has long taken the position that digital assets are treated the same as other property and are taxed when you receive them as payment for a transaction or where you sell them or trade them in a transaction. Like other property, digital assets are not taxed when you receive them for cash.

However, issues have come up when digital assets are received for other purposes, such as through forks, mining or staking — transactions involving digital assets which as capital assets would be reported on Form 8949.

The recent focus by the IRS has been on broker reporting of digital asset transactions to try to reduce noncompliance in the area. The Infrastructure Investment and Jobs Act authorized the broker reporting of digital assets. Form 1099-B, the existing broker reporting form, was initially used for the reporting requirement. Questions arose, however, as to who is a broker in the digital assets context and whether the entities that the IRS designated as digital asset brokers have the information to make the required reports to the IRS.

The IRS has now developed Form 1099-DA for digital assets. Final regulations on broker reporting were issued on June 28, 2024. The service is hoping to be able to match Form 1099-DA reports from brokers to Form 8949 reports from taxpayers.

Form 1040 reporting

For 2024 tax returns, the digital asset question on the Form 1040 has not changed from 2023: “At any time during 2024, did you: (a) receive (as a reward, award or payment for property or services); or (b) sell, exchange or otherwise dispose of a digital asset (or a financial interest in a digital asset)?”

There are disputes between the IRS and the crypto industry about when crypto is converted into something else. For example, there is currently litigation over whether rewards of additional crypto for staking — the process of locking up your cryptocurrency in a wallet to help run a blockchain — results in a taxable transaction (the view of the IRS if the taxpayer has the ability to sell, exchange or otherwise dispose of the rewards) or a nontaxable transaction (the Jarrett cases).

In Revenue Ruling 2023-14, the IRS reaffirmed its position that staking rewards are taxable. The IRS issued a refund in the first Jarrett case to get a court decision that the issue was moot and no decision on the merits was made. In Rev. Rul. 2023-14, the IRS did not provide any guidance as to how staking awards should be valued. It also stated that it was taking no position at the time as to whether “gas” fees paid to a validator for the cost of the computing power used in the validation process are taxable.

Since digital assets are not viewed by the IRS as securities, the wash sale rules do not apply to digital asset transactions. Digital assets treated as capital assets qualify, along with other capital assets, for tax loss harvesting.

Broker reporting

The issues that have come up with broker reporting of digital asset transactions include who is a broker; getting the brokers to report not only the values of digital assets at the time of the transaction but also the cost basis of those assets; helping broker reporting match taxpayer reporting; and determining what information is available to the brokers to comply with filing the Form 1099-DA.

The final version of the 2025 1099-DA was issued on Jan. 10, 2025. It is to be used for 2025 transactions and issued by Feb. 17, 2026 (electronically by March 31, 2026). The instructions discuss reporting of when the broker is using customer-provided information (Box 8), dates of transfer (Box 12b), and reporting of nonfungible tokens and stable coins.

To assist traditional brokers who only have limited involvement with digital assets, Form 1099-B may still be used for tokenized securities settled or cleared on a limited-access regulated network. To assist brokers in transitioning to the new reporting requirements, the IRS is deferring broker reporting of the cash basis on digital assets until 2026. The IRS is also planning to require that, in determining the digital assets to look at for the cost basis, the taxpayer look only to the particular wallet or account held by the broker, again so that the 1099-DA information is more likely to match the information on the tax return.

Crypto tax

There are issues with calculating the crypto cost basis to apply. Taxpayers would generally prefer to apply specific identification by the taxpayer so that the taxpayer can select the highest-basis crypto that is being sold. The IRS wants the broker custodian of the crypto and even trading front-end service providers (DeFi brokers) to report the cost basis on Form 1099-DA.

The service is also proposing that, to help the crypto broker reporting on Form 1099-DA match what the taxpayer is reporting on the tax return, the cost basis be determined separately for each wallet, rather than being able to combine all similar crypto held in separate wallets. For 2025, Form 1099-DA is being required to be filed by crypto brokers; however, the cost basis is not being required. Litigation is also challenging the application of the broker reporting requirements to DeFi brokers.

Revenue Procedure 2024-28 provides a safe harbor under Code Sec. 1012(c)(1) to allocate unused basis of digital assets held within each wallet or account of the taxpayer as of Jan. 1, 2025. The default allocation of basis is based on first-in/first-out principles; however, the taxpayer or the broker, as directed by the taxpayer, may utilize specific identification. The deadline for making the allocation is the earlier of the date of the first sale in the year or the due date for the 2025 tax return. Frequently asked questions provide guidance as to when specific identification can be used.

Notice 2024-56 provides transitional relief to brokers who fail to report sales of digital assets or fail to do back-up withholding. It also permits brokers to rely on uncertified taxpayer identification numbers for 2026. Several types of transactions are specifically excluded from broker reporting requirements. Notice 2024-57 provides related penalty relief for brokers’ failure to file information returns.

To help crypto brokers get their technology together to do cost-basis reporting, the IRS has delayed the crypto cost-basis reporting requirement until after Dec. 31, 2025. This permits taxpayers to continue to use specific identification for crypto transactions based on the taxpayer’s books and records rather than the broker’s 1099-DA report for 2025. FIFO remains the default treatment for 2025 if the taxpayer does not do specific identification.

Summary

The IRS is still struggling to keep up with all the forms of digital asset transactions as they are developed. It is also struggling to get effective third-party reporting by brokers in order to reduce taxpayer noncompliance. In the meantime, the crypto industry hopes that the Trump administration might have a friendlier tax view of crypto transactions, and the IRS focus might change under new leadership.

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White House establishes Strategic Bitcoin Reserve

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The White House today issued an executive order formally creating a Strategic Bitcoin Reserve as well as a U.S. Digital Asset Stockpile. 

The reserve will treat bitcoin, the first and most popular blockchain-based cryptocurrency, as a reserve asset. It will be capitalized with tokens owned by the Department of Treasury that was forfeited as part of criminal or civil asset forfeiture proceedings. Other agencies, such as the FBI, will evaluate their legal authority to transfer any bitcoin owned by those agencies to the Strategic Bitcoin Reserve. The administration said that the U.S. will not actually sell these bitcoins, as they would act as a store of reserve assets. The executive order authorizes the Secretaries of Treasury and Commerce to develop budget-neutral strategies for acquiring additional bitcoin, provided that those strategies impose no incremental costs on American taxpayers.

The U.S. Digital Asset Stockpile, meanwhile, will consist of digital assets other than bitcoin owned by the Department of Treasury that was forfeited in criminal or civil asset forfeiture proceedings. Versus the bitcoin reserve, the government will not acquire additional assets for the U.S. Digital Asset Stockpile beyond those obtained through forfeiture proceedings. Also unlike the bitcoin reserve, the Secretary of the Treasury may determine strategies for responsible stewardship, including potential sales from the U.S. Digital Asset Stockpile.

The executive order also says that agencies must provide a full accounting of their digital asset holdings to the Secretary of the Treasury and the President’s Working Group on Digital Asset Markets.

The administration justified the decision by saying that, with a fixed supply of 21 million coins, there is a strategic advantage to being among the first nations to create a Strategic Bitcoin Reserve, though it did not elaborate. It also said that the government currently holds a significant amount of bitcoin but has not maximized its strategic position as a unique store of value in the global financial system. It decried $17 billion worth of what it called “premature” sales of bitcoin. It also pointed out that there has not been a centralized policy for managing digital asset reserves held by the government, so right now holdings are scattered throughout different departments. 

“Taking affirmative steps to centralize ownership, control, and management of these assets within the Federal government will ensure proper oversight, accurate tracking, and a cohesive approach to managing the government’s cryptocurrency holdings. This move harnesses the power of digital assets for national prosperity, rather than letting them languish in limbo,” said the executive order. 

Dr. Sean Stein Smith, a Lehman College accounting professor who is also chair of the Accounting Working Group in the Wall Street Blockchain Alliance, said that while the executive order only sets up a framework for now, there will be significant implications further down the road. One possibility is an increased emphasis on crypto audits, as David Sack, AI and Crypto Czar, stated multiple times that one of the first pieces of business to move the E.O. forward would be to conduct on audit of current U.S. holdings. With buy-in from the Executive branch, and the emphasis on the importance of crypto audits, said Smith, the profession has an opportunity to expand efforts to standardize the currently disparate crypto audit practices.

Another impact will be client FOMO, as people may reason “after all if it is good enough for the U.S. government it should be good enough for me?” It will be especially important for accountants to educate clients about the risk and opportunities of crypto investments as well as to provide advisory services to those clients interested in integrating crypto into operations.

“In short the E.O. establishing an SBR and digital asset stockpile are set to further propel interest in crypto investments and utilization at clients of all sizes. The emphasis on high quality crypto audits, internal control and advisory opportunities as more investors (retail and institutional) potentially move into the sector, and the inevitable tax issues that will arise as a result all present opportunities for the profession,” said Smith in an email.

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As AI rises in importance, so too does governance

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AI governance was a major theme of 2024, and as the technology continues to evolve, oversight and control—as well as ways to demonstrate it to others—will become even more important this year. 

This was the assessment of Danny Manimbo, a principal with Top 50 firm Schellman, who is primarily responsible for leading the firm’s AI and ISO practices. Speaking during the firm’s Schellmancon event today, he said that last year saw the release of a number of AI governance frameworks, including the National Institute of Standards and Technology’s AI Risk Management Framework, the International Standards Organization’s ISO 42001, and Microsoft’s revisions to its Supplier Security and Privacy Assurance Program to account for AI. Meanwhile, actual regulation is also gaining momentum, with Manimbo pointing to the EU’s AI Act, South Korea’s AI Basic Act, and a number of state-level regulations such as California’s recent AI laws. 

“That kind of set the tone for a lot of the inquiries and the interest that we saw, and for the trends on where GRC was going in 2024, maybe not so much immediately in the beginning of the year, because the frameworks were so new, but I think they were boosted by a number of things in the regulatory standpoint,” said Manimbo. 

The other panelist, Lisa Hall, chief information security officer for the trust platform SafeBase, added that, given the pace of AI advances, it is likely that last year’s measures were not the end but just the beginning, especially considering how widely used even the current generation of solutions is. 

“I think it’s only going to increase, and everyone seems to have some type of AI offering,” said Hall. “Regulations and standards will likely become more demanding, and even with the shadow IT capabilities we have now, I worry that we may be underestimating how often AI technologies are actually used by our employees. And also, on the flip side, how can we best leverage these to make our lives easier?”

Manimbo noted that, with this rise in control frameworks and regulation, this year will also see a rise in demand for ways to demonstrate that one is aligned and compliant with them. The ISO 42001 certification, for which Schellman recently became the first ANSI-accredited body allowed to audit and grant certification for compliance with the standard, is one example, but he anticipated other avenues will open this year. “For example, I sit on the [Cloud Security Alliance] AI Control Framework [board], and they are launching a program scheduled for the second half of this year which is going to be very similar to their [Security Trust Assurance and Risk] program for cloud security but specific to AI risk. That’ll be another avenue,” he said. He added that other standard setters, like the AICPA, might also decide to update their frameworks to account for AI risk. 

Such demonstrations are vital for establishing customer trust in a world that is increasingly connected. Hall noted that supply chains have grown much more complex, which has allowed attackers new opportunities to target vendors or third party software providers and compromise multiple downstream organizations at once. In such an environment, establishing trust with a customer is vital, but it can often involve lengthy and tedious audits filled with manual processes. While she has had success with some automation, such as using AI to reduce time on customer questionnaires and automate access controls, there remain many things that still need human intervention. 

“I’ve definitely struggled with that, like where an auditor is asking for data sets, you’re coming back with a sample set, you’re bouncing back and forth from a tool to gather evidence, and it becomes even more complex when you’re dealing with customer audits and you’re talking to more than one auditor, and you can only reuse evidence for so long that evidence goes stale,” she said. “And then a lot of times, auditors have competing platforms and tools that may not integrate with yours. So it’s still a manual process. There’s a ton of back and forth communication there. I’m still copying and pasting, I’m still downloading from here and uploading to here. So I’d love to see this process improve,”  

Manimbo noted AI has also been helping processes like this, noting that AI can itself help bolster an organization’s controls through automating routine processes and reducing dependence on manual processes. 

“On this front, some of the things that have plagued us in the past is the amount of context that we need as professionals to know if something is something that needs to be addressed immediately as part of a control failure that may be detected. And I think AI will help provide that context there… It may not necessarily be [about] what the controls may be, but how efficient are the models in augmenting existing automation to find those failures in a way that we can effectively address those findings in a way that we can again improve on those and so hopefully reducing additional burden on a team members,” he said. 

However, with all these different frameworks coming out, and with current ones being revised to account for AI, professionals may be challenged in keeping up with all the changes. Professionals need to not only know how to apply these frameworks but also how to scale them as time goes on. Hall said that, by maintaining a security-focused mindset and being proactive, so that the organization is more able to respond to change. 

“If we build and buy with security in mind and find ways to leverage automation and AI to enable us to quickly adjust, … we’re just going to be way better off,” said Hall.  “Instead of looking at ‘here’s the strict regulation, here’s what I have to do,’ [it is] kind of this afterthought, by being more proactive and just having these things in mind. .. I think it’s about us having that mindset of: How is the security built in? How can I be accountable and prove that I’m doing what I’m doing? And think about that before the auditors show up and before the regulations show up.”

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AICPA in discussions with IRS over tax season jitters

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The American Institute of CPAs is monitoring the situation at the Internal Revenue Service amid reports of layoffs of up to half the staff, keeping in touch with IRS officials about maintaining services during the critical tax season.

“In recent weeks, there has been a flood of information regarding the current state of the IRS, some of which has resulted in conflicting reports, creating confusion,” said AICPA president and CEO Mark Koziel in a statement Friday. “The AICPA is having active discussions with IRS officials to clarify this information and we are actively monitoring developments as the IRS continues to assess the immediate and long-term implications. With the volatility of the present environment and rapidly changing events, it is important to reconcile fact from fiction for taxpayers and their advisors. Despite inconsistent reports, we know that the IRS is making every effort to maintain this tax season’s service levels comparable with that of recent years.”

He stressed the importance of the IRS maintaining service during tax season.

“The ability of the IRS to maintain service levels for taxpayers and their preparers is critically important to the AICPA,” Koziel added. “IRS services in combination with modernization efforts, which include technology advancements, have been the bedrock of AICPA’s recommendations for many years. A modern, functioning IRS is essential for Americans to meet their tax obligations and to our country’s financial health.”

The AICPA is also offering recommendations to the embattled agency. “The AICPA continues to provide recommendations to the IRS that will offer some level of relief as we work diligently to understand the impacts to services offered to taxpayers and their practitioners,” said Koziel. “We offer our voice and support to minimize public confusion about current IRS operations.”

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