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.
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.
Cisco Systems shares spiked higher Wednesday evening after the networking company delivered a quarterly beat and outlook raise. Another quarter of double-digit order growth proves Cisco is an underrated winner from the AI infrastructure buildout. Revenue in the company’s fiscal 2026 first quarter, which ended Oct. 25, increased 8% year over year to $14.88 billion, exceeding the LSEG-complied analyst consensus estimate of $14.76 billion. Non-GAAP earnings increased 10% on an annual basis to $1 per share, beating expectations of 98 cents, LSEG data showed. GAAP stands for generally accepted accounting principles. CSCO YTD mountain Cisco Systems YTD Look at the shares of Cisco go. They surged more than 7% in after-hours trading to just about $80 per share. That’s on top of a 3% move in regular trading hours. If the stock can take out $80.06, it will make its first all-time high since March 2000. Shares, as of Wednesday’s close, rose roughly 25% year to date. Bottom line It’s a deserving move after an excellent quarter, highlighted by accelerating product order growth, especially from artificial intelligence customers. During the post-earnings call, Cisco CEO Chuck Robbins attributed the strength in AI orders to a “deepening” relationship with existing customers. The company also called out that a “major multi-year, multi-billion-dollar campus networking refresh cycle” is underway. It wasn’t all perfect, however, as the security business missed estimates, with revenue falling year over year. According to management, some revenue recognition timing issues need to be sorted out. Security weakness was our main concern ahead of the quarter. The business also missed revenue estimates in the prior quarter, and we didn’t think a quick turnaround was likely. Our fear of this repeat was the main reason why we took some profits in this position Monday at around $71. Even though we were right to be cautious on security, the market was turning a blind eye to this issue because of how fast networking is growing. A rebound in security also isn’t needed for management to hit on its outlook, which was raised well above Street estimates Wednesday evening. Another concern of the bears entering earnings was that Cisco would be negatively impacted by the government shutdown due to its large federal agencies business. Despite the closed government, Robbins noted this business managed to grow orders by a high single-digit percentage in the quarter. He’s anticipating upside in orders once the government reopens. Why we own it Cisco Systems is an enterprise networking equipment provider that has made big strides to appeal to cloud customers. The company has also increased its presence in the security market through its acquisition of Splunk. In addition, Cisco’s long-term transition toward subscription software sales, which are sticky and come with higher margins, should help improve the stock’s undemanding price-to-earnings multiple. Competitors : Arista Networks , Hewlett Packard Enterprise , Juniper Networks Most recent buy : Aug. 19, 2025 Initiated : July 17, 2025 The story remains that Cisco has turned into a sleeper AI play thanks to the billions of dollars it is taking in from hyperscaler customers. That surge of orders is converting to big revenue. In fiscal year 2025, Cisco recognized roughly $1 billion of AI revenue from hyperscalers, which are the biggest of the Big Tech names, such as the major cloud companies. On the call, Robbins said he expects to recognize roughly $3 billion from hyperscalers in fiscal year 2026. Despite this accelerating growth and subscription revenue making up more than half of its total revenue, the stock still trades at a reasonable price-to-earnings multiple of about 19.5 times based on the new midpoint of management’s full-year adjusted earnings-per-share (EPS) outlook. We’re reiterating our 2 rating because we don’t like to chase stock spikes, but we are increasing our price target to $85 per share from $78. Commentary Total Product orders increased 13% year over year – an acceleration from 7% growth in the prior quarter – with growth across all geographies and customer markets. When we review Cisco, we always focus on orders because that’s the best leading indicator of where revenue is headed. Product revenue grew 10% year over year to $7.77 billion, beating estimates of about $7.47 billion. Starting with the Networking sub-segment, product orders increased by a high teens rate, representing the fifth consecutive quarter of double-digit growth. AI infrastructure orders from hyperscaler customers were a big driver of that growth. Cisco took in $1.3 billion of orders in the quarter, an acceleration from the more than $800 million in the prior quarter. The company also saw strong orders for enterprise routing, campus switching, wireless, industrial IoT, and servers. Credit Cisco’s close relationships with portfolio name Nvidia and Advanced Micro Devices for its recent AI success. Last month, Cisco announced the N9100, which they called the first Nvidia partner developed data center switch based on Nvidia Spectrum-X Ethernet switch silicon. “The N9100, available in the second half of fiscal year 2026, will provide the operational consistency and flexibility needed for sovereign and neocloud providers to build and manage AI at scale,” Robbins explained. Neoclouds are next-generation specialized clouds for accelerated computing. CoreWeave , which rents cloud-based Nvidia chips for AI tasks, is an example of a neocloud. Cisco is also helping G42, leading United Arab Emirates AI firm, with powering, connecting, and securing its large-scale AI clusters with AMD graphics processing units (GPUs) The enterprise AI story is starting to emerge, too. Cisco experienced strong demand for switching, routing, and wireless products, which Robbins said is an indication of customers “investing in the connectivity needed for AI deployments.” Across sovereign, neocloud, and enterprise customers, Robbins called out a growing pipeline above $2 billion for its high performance networking products. This comes after Cisco booked $200 million of orders in its fiscal first quarter from these customers. By division, Networking revenue increased 15% to $7.77 billion, beating estimates. The largest driver of this increase in sales was from service provider routing, which is mostly from AI infrastructure. Data center switches and enterprise routing were also up double digits, while campus switching revenue increased by a high single digit percentage. In the Security division, revenue fell 2% year over year and missed analysts’ forecasts again. It’s disappointing to see a sizeable miss in back-to-back quarters, but management attributed the decline to a timing issue. Robbins explained that more customers are using Splunk’s offerings through cloud subscriptions instead of on-premise deals, leading to a timing change of when revenue is recognized. Ultimately, this transition isn’t a bad thing. The company is in favor of more subscription-based revenue. Cisco completed its $28 billion acquisition of Splunk in March 2024. “We are actually pleased to see more cloud subscriptions for Splunk as they enable greater adoption and expansion, and allow us to deliver innovation faster to enable customers to unlock value from AI Now ” Robbins explained on the call. More broadly. Cisco said it continued to see order growth for some of it newer and refreshed security products, which make up about one third of the portfolio, while its order products are in decline. Importantly, management doesn’t believe Security’s stumbles will last long. They expect revenue growth to accelerate and end the year at a much higher rate. But even if that doesn’t happen and the results don’t materially improve from here, Cisco said it’s still confident in its ability to deliver on its fiscal Q2 and full year 2026 outlook. The Collaboration and Observability units saw revenue drop 3% and rise 6%, respectively, with Collaboration missing estimates and Observability matching expectations. Services revenue increased 2% year over year to $3.81 billion, slightly beating estimates. As always, we appreciate Cisco’s consistent approach to returning cash to shareholders. The company repurchased $2 billion worth of shares in the quarter at an average price of $68.28. That looks like a great trade since the stock is knocking on the door of $80 in after-hours trading. It has $12.2 billion remaining under its authorization. Cisco stock, as of Wednesday’s closing price, has a 2.2% annual dividend yield. Guidance Cisco expects fiscal 2026 second-quarter revenue of $15 billion to $15.2 billion, which is well above the consensus estimate of $14.62 billion. It also sees non-GAAP EPS of $1.01 to $1.03 cents, which is nicely above the consensus estimate of 98 cents. For full year 2026, Cisco now expects revenue of $60.2 billion to $61 billion, which is about a $1 billion increase from the prior outlook of $59 billion to $60 billion. This revised outlook exceeds the consensus estimate of $59.64 billion. On the bottom line, management raised its EPS forecast to $4.08 to $4.14 from its prior outlook of $4.00 to $4.06. This new midpoint of $4.11 is better than the consensus analyst estimate by 7 cents. (Jim Cramer’s Charitable Trust is long CSCO, NVDA. See here for a full list of the stocks.) As a subscriber to the CNBC Investing Club with Jim Cramer, you will receive a trade alert before Jim makes a trade. Jim waits 45 minutes after sending a trade alert before buying or selling a stock in his charitable trust’s portfolio. If Jim has talked about a stock on CNBC TV, he waits 72 hours after issuing the trade alert before executing the trade. THE ABOVE INVESTING CLUB INFORMATION IS SUBJECT TO OUR TERMS AND CONDITIONS AND PRIVACY POLICY , TOGETHER WITH OUR DISCLAIMER . NO FIDUCIARY OBLIGATION OR DUTY EXISTS, OR IS CREATED, BY VIRTUE OF YOUR RECEIPT OF ANY INFORMATION PROVIDED IN CONNECTION WITH THE INVESTING CLUB. NO SPECIFIC OUTCOME OR PROFIT IS GUARANTEED.
Traders work on the floor of the New York Stock Exchange (NYSE) on Nov. 12, 2025 in New York City.
Spencer Platt | Getty Images
The divergence between the performance of the Dow Jones Industrial Average and Nasdaq Composite on Wednesday stateside reinforces the suggestion that there are two markets operating in the U.S.: one of an artificial intelligence and another of “everything else.”
Not only did the Dow rise, it also secured its second consecutive record high and closed above the 48,000 level for the first time.
The index, which comprises 30 blue-chip companies, is typically seen as a marker of the “old economy.” That is to say, it is mostly made up of large, well-established companies driving the U.S. economy, such as banks, healthcare and industrials, before Silicon Valley became a minisun powering everything.
To be sure, new and flashy names, such as Nvidia and Salesforce, constitute the Dow too. But as the index is price-weighted, meaning that companies with higher share prices influence the Dow more, tech companies don’t exert as much gravity on it.
That’s in contrast to the Nasdaq, which is weighted by companies’ market capitalization, and dominated mainly by technology firms. The tech-heavy index fell as shares like Oracle and Palantir slipped — even Advanced Micro Devices’ 9% pop on its growth prospects couldn’t rescue the Nasdaq from the red.
It’s not necessarily a warning sign about overexuberance in AI.
“There’s nothing wrong, in our view, of kind of trimming back, taking some gains and re-diversifying across other spots in the equity markets,” said Josh Chastant, portfolio manager of public investments at GuideStone Fund.
But what investors would really like is if fork in the road merges into one. That tends to be the safer path to take.
Anthropic to spend $50 billion on U.S. AI infrastructure. Custom data centers will be first built in Texas and New York and go live in 2026, with more locations to follow. The facilities will be developed with Fluidstack, an AI cloud platform.
U.S.October jobs and inflation data might not be released. White House press secretary Karoline Leavitt told reporters that part of the fallout of the government closure could be lasting damage to the government’s data collection ability. But analysts think otherwise.
U.S. House of Representatives heading toward a vote. The House on Wednesday night stateside cleared a procedural hurdle required before the vote could begin on a bill that would end the government shutdown. Voting is expected to happen as of publication time.
[PRO] This U.S. mining stock is a top play: CIO. U.K. fundBlue Whale Capital’s Stephen Yiu said macroeconomic concerns, such as the U.S. fiscal deficit and the weakness of the dollar, could support the stock.
And finally…
People walk by the New York Stock Exchange (NYSE) on June 18, 2024 in New York City.
Private equity firms are facing a new reality: a growing crop of companies that can neither thrive nor die, lingering in portfolios like the undead.
These so-called “zombie companies” refer to businesses that aren’t growing, barely generate enough cash to service debt and are unable to attract buyers even at a discount. They are usually trapped on a fund’s balance sheet beyond its expected holding period.
Jason Kim, chief executive officer of Firefly Aerospace, center, during the company’s initial public offering at the Nasdaq MarketSite in New York, US, on Thursday, Aug. 7, 2025.
Michael Nagle | Bloomberg | Getty Images
Firefly Aerospace‘s stock surged 15% on Wednesday after the space technology company issued better-than-expected third-quarter results and lifted its guidance.
Revenues in the third quarter jumped nearly 38% to $30.8 million from $22.4 million in the year-ago period and nearly doubled from the previous quarter.
Firefly’s net loss totaled $140.4 million, or $1.50 per share. The company said net loss included costs tied to its IPO, foreign exchange and executive severance
The company also lifted its outlook for the year, saying it now expects revenues to range between $150 million and $158 million. That’s up from previous guidance in the range of $133 million and $145 million.
This is Firefly’s second quarterly report as a public company. Last quarter, shares slumped after it posted a bigger loss and lower revenues than analysts were expecting.
The Cedar Park, Texas, company went public on the Nasdaq in August during a period of heightened enthusiasm toward space technology. The U.S. government and NASA have leaned on more contracts with companies like Firefly and Elon Musk‘s SpaceX to support moon missions.
But shares of Firefly have lost 70% of their value since their opening day close, and the company’s market capitalization has plummeted from about $8.5 billion to about $2.7 billion on Wednesday.
In September, Firefly shares sank after a rocket exploded during a ground test at the company’s Texas facility, days after receiving clearance from the Federal Aviation Administration over a separate incident. Firefly has since put “corrective measures” in place, the company said on Wednesday. Shares dropped 35% in September and are down 24% this month.
