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For years, cryptocurrency holdings of U.S. taxpayers have existed in a sort of reporting gray zone. But now, those crypto wallets are getting a whole lot of attention from the Internal Revenue Service and President Biden, who appear determined to crack down on tax cheats.

The timing makes sense.

The president needs to raise money, relatively quickly, for his own ambitious economic agenda. And the “tax gap,” which is the difference between taxes paid and taxes owed, is a big pool of cash ripe for the picking. IRS chief Charles Rettig says the country is losing about a trillion dollars every year in unpaid taxes, and he credits this growing tax gap, at least in part, to the rise of the crypto market.

The federal government is so convinced of the potential for income from back-due taxes that the White House wants to give the IRS an extra $80 billion and new powers to crack down on tax dodgers, including those parking their cash in crypto. 

“The IRS is in the business of collecting revenue,” said Shehan Chandrasekera, CPA, and head of tax strategy at CoinTracker.io, a crypto tax software company. 

“Historically, if they spend $1 for any type of enforcement activity, they make $5…I think crypto enforcement activities are even higher than that,” he said.

Non-compliance made easy

In the U.S., it is easy to be an unintentional crypto tax cheat.

For one, the IRS hasn’t exactly made it easy to report this information. 

Tax year 2019 was the first time the IRS explicitly asked taxpayers whether they had dealt in crypto. A question on form Schedule 1 read, “At any time during 2019, did you receive, sell, send, exchange or otherwise acquire any financial interest in any virtual currency?”

But experts said the question was vague, and crucially, not everyone files this specific document. A Schedule 1 is typically used to report income not listed on the Form 1040, such as capital gains, alimony, or gambling winnings. 

So in 2020, the IRS upped its game by moving the virtual currency question to the 1040 itself, which is used by all individuals filing an annual income tax return. 

“[They put it] right after your name and social security number, and before you put any income numbers or deduction numbers in,” explained Lewis Taub, CPA and director of tax services at Berkowitz Pollack Brant. This made the question virtually impossible to miss. 

But perhaps the bigger issue, according to Shehan, is that many filers have no clue how to calculate their crypto capital gains and losses.

If you trade through a brokerage, you typically get a Form 1099-B spelling out your transaction proceeds, streamlining the reporting process.

That doesn’t happen in the crypto world, Shehan said. “Many crypto exchanges don’t report any information to the IRS.” 

While some crypto exchanges have begun to issue a tax form known as the 1099-K – which is traditionally given to an individual who engages in at least 200 transactions worth an aggregate $20,000 or more – in the context of crypto, this form only reports the total value of transactions. The total value does not factor in how much the person paid for the cryptocurrency in the first place, something referred to as the “cost basis,” which makes it hard to calculate the taxable gain.

“A lot of people have actually over-reported their income, because they got confused,” explained Shehan. 

But the biggest issue driving non-compliance is the fact that the tax rules surrounding digital currencies are still being worked out, and in a state of constant flux.

‘Taxable event’

The IRS treats virtual currencies like bitcoin as property, meaning that it is taxed in a manner similar to stocks or real property. If you buy one bitcoin for $10,000 and sell it for $50,000, you face $40,000 of taxable capital gains. While this concept is relatively simple, it isn’t always clear what constitutes a “taxable event.”

Is buying dogecoin with your bitcoin a taxable event? Purchasing a TV with your dogecoin? Buyingan NFT with ether? 

All of the above are technically taxable events.

“The government says if I buy something with crypto, it is as if I liquidated my crypto no differently than if I sold any other property,” said Taub.

Mining dogecoin for fun qualifies as self-employment income in the eyes of the government. According to cryptocurrency tax software TaxBit – which recently contracted with the IRS to aid the agency in digital currency-related audits – tax rates vary between 10-37% on mining proceeds. 

“Crypto miners have to pay taxes on the fair market value of the mined coins at the time of receipt,” wrote crypto tax attorney Justin Woodward. While there are ways to get creative to minimize this tax burden, such as classifying mining as a business and deducting equipment and electricity expenses, it takes a bit of filing acrobatics to make it work.  

Earning interest on the bitcoin sitting idle in your crypto wallet also counts as income and is taxed as such. Exchanges like Coinbase have also begun to send Form 1099-MISC to taxpayers who earned $600 or more on crypto rewards or staking. 

The IRS crypto crackdown

Crypto trading volume may have fallen off a cliff in the last few weeks, but the overall market value of digital currencies is still up about 75% this year. The IRS has made it clear that it wants a piece of the action.

The agency recently ramped up efforts to subpoena centralized crypto exchanges for information about noncompliant U.S. taxpayers. 

This spring, courts authorized the IRS to issue John Doe summonses to crypto exchange operators Kraken and Circle as a way to find individuals who conducted at least $20,000 of transactions in cryptocurrency from 2016 to 2020. 

The IRS also put this same type of summons to use in 2016, when it went after Coinbase crypto transactions from 2013 to 2015.

Issuing these summons one exchange at a time is a clumsy way to capture noncompliant U.S. taxpayers, but it can be effective, according to Jon Feldhammer, a partner at law firm Baker Botts and a former IRS senior litigator.

In 2019, the IRS announced it was sending letters to more than 10,000 people who potentially failed to report crypto income. 

Rettig said in a statement that taxpayers should take the letter “very seriously by reviewing their tax filings and when appropriate, amend past returns and pay back taxes, interest and penalties.”

Sample Letter 6173
IRS

According to Shehan, the infamous “Letter 6173” gave individuals 30 days to respond to the IRS, otherwise they risked having their tax profile examined. Letters went out again in 2020, and a fresh round of these stern warnings are expected to be sent this autumn.

Even the threat of a letter has a lot of people seeking the counsel of accountants as to whether they should get ahead of a potential audit and be proactive about amending past returns.

“A lot of people ask me on Twitter: ‘Oh my god, in 2018, I had $200 worth of capital gains I didn’t report. What should I do?'” recounted Shehan. “In that case, it just is not worth amending the return to pick up $200 worth of income…The high-level thing is that if you didn’t do anything intentionally, you are fine.”

The IRS is also getting smarter about uncovering crypto tax evaders with the help of new data analytic tools it can employ in-house. 

The agency’s partnership with TaxBit is a part of this effort. Taub describes the software as being able to go through cryptocurrency wallets and analyze them to figure out what was bought and sold in crypto. In addition to enlisting the services of the vendor itself, Taub says that IRS agents are being trained up on the software as a way to identify tax dodgers.

Biden’s new crypto rules

The president’s 2022 budget proposal could lead to a raft of new crypto reporting requirements for those dealing in digital coins.

The U.S. Treasury Department’s new “Greenbook,” released in May, calls for more comprehensive reporting requirements for crypto, so it’s as hard to spend digital currencies without getting reported as it is to spend cash today.

One proposal would require businesses to report to the IRS all cryptocurrency transactions valued at more than $10,000. Another calls for crypto asset exchanges and custodians to report data on user accounts which conduct at least $600 worth of gross inflows or outflows in a given year.

Another potential major blow to crypto holders: Biden’s proposal to raise the top tax rate on long-term capital gains to 43.4%, up from 23.8%

“Crypto gains are being taxed as any other type of gain in assets, either at long-term capital gains or ordinary rates. President Biden has proposed to eliminate the difference between the two,” said David Lesperance, a Toronto-based attorney who specializes in relocating the rich. 

Lesperance told CNBC the proposal would also function retroactively and apply to any transactions which took place after April 28, 2020. 

“This translates into $19,800 in increased capital gains tax for each $100,000 in capital appreciation of crypto,” he said.

Amid the rising crypto crackdown here in the U.S., Lesperance has helped clients to expatriate in order to ditch their tax burden altogether. 

“By exercising a properly executed expatriation strategy, the first $750,000 in capital appreciation is tax-free and the individual can organize themselves to pay no U.S. tax at all in the future,” he said. 

But Lesperance warned that taxpayers need to move fast. “The runway to execute this strategy is very short,” he said.

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‘AI may eat software,’ but several tech names just wrapped a huge week

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'AI may eat software,' but several tech names just wrapped a huge week

A banner for Snowflake Inc. is displayed at the New York Stock Exchange to celebrate the company’s initial public offering on Sept. 16, 2020.

Brendan McDermid | Reuters

MongoDB’s stock just closed out its best week on record, leading a rally in enterprise technology companies that are seeing tailwinds from the artificial intelligence boom.

In addition to MongoDB’s 44% rally, Pure Storage soared 33%, its second-sharpest gain ever, while Snowflake jumped 21%. Autodesk rose 8.4%.

Since generative AI started taking off in late 2022 following the launch of OpenAI’s ChatGPT, the big winners have been Nvidia, for its graphics processing units, as well as the cloud vendors like Microsoft, Google and Oracle, and companies packaging and selling GPUs, such as Dell and Super Micro Computer.

For many cloud software vendors and other enterprise tech companies, Wall Street has been waiting to see if AI will be a boon to their business, or if it might displace it.

Quarterly results this week and commentary from company executives may have eased some of those concerns, showing that the financial benefits of AI are making their way downstream.

MongoDB CEO Dev Ittycheria told CNBC’s “Squawk Box” on Wednesday that enterprise rollouts of AI services are happening, but slowly.

“You start to see deployments of agents to automate back office, maybe automate sales and marketing, but it’s still not yet kind of full force in the enterprise,” Ittycheria said. “People want to see some wins before they deploy more investment.”

Revenue at MongoDB, which sells cloud database services, rose 24% from a year earlier to $591 million, sailing past the $556 million average analyst estimate, according to LSEG. Earnings also exceeded expectations, as did the company’s full-year forecast for profit and revenue.

MongoDB CEO Dev Ittycheria on Q2 results: The opportunity in front of us is massive

MongoDB said in its earnings report that it’s added more than 5,000 customers year-to-date, “the highest ever in the first half of the year.”

“We think that’s a good sign of future growth because a lot of these companies are AI native companies who are coming to MongoDB to run their business,” Ittycheria said.

Pure Storage enjoyed a record pop on Thursday, when the stock jumped 32% to an all-time high.

The data storage management vendor reported quarterly results that topped estimates and lifted its guidance for the year. But what’s exciting investors the most is early returns from Pure’s recent contract with Meta. Pure will help the social media company manage its massive storage needs efficiently with the demands of AI.

Pure said it started recognizing revenue from its Meta deployments in the second quarter, and finance chief Tarek Robbiati said on the earnings call that the company is seeing “increased interest from other hyperscalers” looking to replace their traditional storage with Pure’s technology.

‘Banger of a report’

Reports from MongoDB and Pure landed the same week that Nvidia announced quarterly earnings, and said revenue soared 56% from a year earlier, marking a ninth-straight quarter of growth in excess of 50%.

Nvidia has emerged as the world’s most-valuable company by selling advanced AI processors to all of the infrastructure providers and model developers.

While growth at Nvidia has slowed from its triple-digit rate in 2023 and 2024, it’s still expanding at a much faster pace than its megacap peers, indicating that there’s no end in sight when it comes to the expansive AI buildouts.

“It was a banger of a report,” said Brad Gerstner CEO of Altimeter Capital, in an interview with CNBC’s “Halftime Report” on Thursday. “This company is accelerating at scale.”

Read more CNBC tech news

Data analytics vendor Snowflake talked up its Snowflake AI data cloud in its quarterly earnings report on Wednesday.

Snowflake shares popped 20% following better-than-expected earnings and revenue. The company also boosted its guidance for the year for product revenue, and said it has more than 6,100 customers using Snowflake AI, up from 5,200 during the prior quarter.

“Our progress with AI has been remarkable,” Snowflake CEO Sridhar Ramaswamy said on the earnings call. “Today, AI is a core reason why customers are choosing Snowflake, influencing nearly 50% of new logos won in Q2.”

Autodesk, founded in 1982, has been around much longer than MongoDB, Pure Storage or Snowflake. The company is known for its AutoCAD software used in architecture and construction.

The company has underperformed the broader tech sector of late, and last year activist investor Starboard Value jumped into the stock to push for improvements in operations and financial performance, including cost cuts. In February, Autodesk slashed 9% of its workforce, and two months later the company settled with Starboard, adding two newcomers to its board.

The stock is still trailing the Nasdaq for the year, but climbed 9.1% on Friday after Autodesk reported results that exceeded Wall Street estimates and increased its full-year revenue guidance.

Last year, Autodesk introduced Project Bernini to develop new AI models and create what it calls “AI‑driven CAD engines.”

On Thursday’s earnings call, CEO Andrew Anagnost was asked what he’s most excited about across his company’s product portfolio when it comes to AI.

Anagnost touted the ability of Autodesk to help customers simplify workflow across products and promoted the Autodesk Assistant as a way to enhance productivity through simple prompts.

He also addressed the elephant in the room: The existential threat that AI presents.

“AI may eat software,” he said, “but it’s not gonna eat Autodesk.”

WATCH: Autodesk CEO on Q2 earnings

Autodesk CEO on Q2 earnings beat, M&A strategy and activist pressure

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Meta changes teen AI chatbot responses as Senate begins probe into ‘romantic’ conversations

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Meta changes teen AI chatbot responses as Senate begins probe into 'romantic' conversations

Meta Platforms CEO Mark Zuckerberg departs after attending a Federal Trade Commission trial that could force the company to unwind its acquisitions of messaging platform WhatsApp and image-sharing app Instagram, at U.S. District Court in Washington, D.C., U.S., April 15, 2025.

Nathan Howard | Reuters

Meta on Friday said it is making temporary changes to its artificial intelligence chatbot policies related to teenagers as lawmakers voice concerns about safety and inappropriate conversations.

The social media giant is now training its AI chatbots so that they do not generate responses to teenagers about subjects like self-harm, suicide, disordered eating and avoid potentially inappropriate romantic conversations, a Meta spokesperson confirmed.

The company said AI chatbots will instead point teenagers to expert resources when appropriate.

“As our community grows and technology evolves, we’re continually learning about how young people may interact with these tools and strengthening our protections accordingly,” the company said in a statement.

Additionally, teenage users of Meta apps like Facebook and Instagram will only be able to access certain AI chatbots intended for educational and skill-development purposes.

The company said it’s unclear how long these temporary modifications will last, but they will begin rolling out over the next few weeks across the company’s apps in English-speaking countries. The “interim changes” are part of the company’s longer-term measures over teen safety.

TechCrunch was first to report the change.

Last week, Sen. Josh Hawley, R-Mo., said that he was launching an investigation into Meta following a Reuters report about the company permitting its AI chatbots to engage in “romantic” and “sensual” conversations with teens and children.

Read more CNBC tech news

The Reuters report described an internal Meta document that detailed permissible AI chatbot behaviors that staff and contract workers should take into account when developing and training the software.  

In one example, the document cited by Reuters said that a chatbot would be allowed to have a romantic conversation with an eight-year-old and could tell the minor that “every inch of you is a masterpiece – a treasure I cherish deeply.”

A Meta spokesperson told Reuters at the time that “The examples and notes in question were and are erroneous and inconsistent with our policies, and have been removed.”

Most recently, the nonprofit advocacy group Common Sense Media released a risk assessment of Meta AI on Thursday and said that it should not be used by anyone under the age of 18, because the “system actively participates in planning dangerous activities, while dismissing legitimate requests for support,” the nonprofit said in a statement.

“This is not a system that needs improvement. It’s a system that needs to be completely rebuilt with safety as the number-one priority, not an afterthought,” said Common Sense Media CEO James Steyer in a statement. “No teen should use Meta AI until its fundamental safety failures are addressed.”

A separate Reuters report published on Friday found “dozens” of flirty AI chatbots based on celebrities like Taylor Swift, Scarlett Johansson, Anne Hathaway and Selena Gomez on Facebook, Instagram and WhatsApp.

The report said that when prompted, the AI chatbots would generate “photorealistic images of their namesakes posing in bathtubs or dressed in lingerie with their legs spread.”

A Meta spokesperson told CNBC in a statement that “the AI-generated imagery of public figures in compromising poses violates our rules.”

“Like others, we permit the generation of images containing public figures, but our policies are intended to prohibit nude, intimate or sexually suggestive imagery,” the Meta spokesperson said. “Meta’s AI Studio rules prohibit the direct impersonation of public figures.”

WATCH: Is the A.I. trade overdone?

The 'Halftime' Investment Committee debate whether the AI trade overdone

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Tesla asks for $243 million verdict to be tossed in fatal Autopilot crash suit

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Tesla asks for 3 million verdict to be tossed in fatal Autopilot crash suit

Dillon Angulo, 33, looks at a roadside memorial sign reading “Drive Safely In Memory Naibel Benavidez” next to the site of a car crash where a Tesla driver using Autopilot killed her, and left him catastrophically injured in 2019, on Aug. 12, 2025, in Key Largo, Florida.

Eva Marie Uzcategui | The Washington Post | Getty Images

Tesla has filed a motion to appeal the verdict in a product liability and wrongful death lawsuit that could cost the company $242.5 million if it is not reduced or overturned.

Elon Musk‘s automaker has asked for the verdict to be tossed or for a new trial in Florida’s Southern district court.

Gibson Dunn, which is representing Tesla in the appeal, argued that compensatory damages in the case should be steeply reduced from $129 million to $69 million at most. That would result in Tesla having to pay a $23 million award if the prior verdict holding the company partially liable for the crash stands up.

The firm also argued that punitive damages should be eliminated or reduced to, at most, three times compensatory damages due to a statutory cap in the state of Florida.

The suit focused on a fatal crash that occurred in 2019 in Key Largo, Florida, in which George McGee was driving his Tesla Model S sedan while using the company’s Enhanced Autopilot, a partially automated driving system.

While driving, McGee dropped his mobile phone and scrambled to pick it up. He said during the trial that he believed Enhanced Autopilot would brake if an obstacle was in the way.

Read more CNBC tech news

McGee’s Model S accelerated through an intersection at just over 60 miles per hour, hitting a nearby empty parked car and its owners, who were standing on the other side of their vehicle.

The collision killed 22-year-old Naibel Benavides and severely injured her boyfriend, Dillon Angulo.

A jury in a Miami federal court earlier this month said that Tesla should compensate the family of the deceased and the injured survivor, paying a $242.5 million portion of a total $329 million in damages that they decided were appropriate.

In their motion to appeal, Tesla’s lawyers argue that the Model S vehicle had no design defects, and that even alleged design defects could not be blamed for the crash, which they say was caused entirely by the driver.

“For as long as drivers remain at the wheel, any safety feature may embolden a few reckless drivers while enhancing safety for countless others,” the appeal states. “Holding Tesla liable for providing drivers with advanced safety features just because a reckless driver overrode them cannot be reconciled with Florida law.”

Tesla did not respond to a request for additional comment.

Brett Schreiber, lead trial counsel for the plaintiffs in this case, said in a statement that he believes the court will uphold the prior verdict, which should not be seen as “an indictment of the autonomous vehicle industry, but of Tesla’s reckless and unsafe development and deployment of its Autopilot system.”  

“The jury heard all the facts and came to the right conclusion that this was a case of shared responsibility but that does not discount the integral role Autopilot and the company’s misrepresentations of its capabilities played in the crash,” he said.

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