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The Coming Crypto Tax Bomb

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Crypto taxpayers are in for a rude awakening.

We’re 16+ years into Bitcoin, yet taxpayers and CPAs still pretend that tax guidance remains unclear or even nonexistent. The IRS is gearing up for a historic wave of compliance audits targeting the crypto space, and taxpayers have no idea what they’re in for.

Last year, the IRS issued Revenue Procedure 2024-28, fundamentally changing how crypto should be tracked from a tax perspective. Providing crystal clear guidance, safe harbors for taxpayers to get compliant, and deadlines to migrate by. The rules are clear, the expectations set, with the IRS quietly positioning itself to issue a wave of compliance audits for those still with their head in the sand.

The reckoning is already beginning as we’re seeing an unprecedented amount of 6174, 6174-A, and 6173 letters being sent out by the IRS.

Typically, this time of the year is quiet. But for the past several weeks, our phone has been ringing non-stop from taxpayers receiving these notices from the IRS demanding they get compliant “or else.” And it’s not just us – crypto tax firms across the board are reporting the same activity, indicating the IRS knows taxpayers have casually engaged in crypto tax evasion, and they are here to collect what they’ve failed to collect for the past decade.

Strategically pairing Rev-Proc 24-28 with the release of the new Form 1099-DA, the IRS is positioned to blindside taxpayers and CPAs who have neglected getting compliant. The 2025 tax year will be pivotal as the IRS now has an abundance of ammunition to use in audits. Gone are the days where taxpayers could defer to defenses like “well, the guidance was unclear, so I just did my best.” The IRS has been explicit, the guidance is clear, and the penalties for non-compliance have been outlined, yet taxpayers and CPAs still assume we’re in the Wild West.

On top of this, Form 1099-DAs will be issued to both taxpayers and the IRS alike by brokers, but there’s a major catch: the form won’t include cost basis for the 2025 tax year, and will almost certainly include incorrect cost basis for years after.

That means when you transfer assets into an exchange and later sell them, the sale gets reported — but the exchange has no idea what you originally paid. In the absence of that information, the form defaults to showing a $0 cost basis. To the IRS or a traditional CPA, it looks like pure profit.

Say you buy 1 ETH for $2,200, move it to Coinbase, and sell it for $2,500. If Coinbase doesn’t have the cost basis, the form shows a $2,500 gain. Your actual gain was $300 — but unless you’ve tracked that basis yourself, the IRS won’t know. And they’ll assume the worst.

A widespread problem

This isn’t a one-off scenario. It’s going to affect hundreds of thousands of taxpayers.

If those inflated gains go uncorrected, they’ll either result in unnecessary tax owed or trigger an audit. And many CPAs won’t catch it, because most still aren’t equipped to handle crypto properly. They don’t understand how wallets work. They confuse transfers with sales. They miss staking rewards and DeFi activity entirely. Clients think their CPA is on top of it. CPAs assume the 1099 is accurate. No one’s double-checking.

That’s where things go wrong. And that’s exactly what the IRS is counting on.

The old defense — that the guidance wasn’t clear — doesn’t hold up anymore. The IRS has been direct. The expectations are spelled out. The time to fix things is NOW, before an enforcement letter is received.

Crypto isn’t some edge case anymore. Tens of millions of Americans have bought, sold, staked, lent, or transferred digital assets. Most have done a poor job keeping records. Some haven’t even tried. The result is a tax system full of underreported gains, misclassified income, inconsistent filings, and the taxman looking for revenge.

The most common mistakes aren’t complex. Transfers between wallets are flagged as sales. Assets appear on exchanges with no cost basis attached. Staking rewards and airdrops go unreported. DeFi activity is missing entirely. And year after year, taxpayers and professionals rely on CSV exports that were never designed for tax reporting in the first place.

These aren’t edge cases. They’re pervasive amongst crypto investors. And at scale, they add up to a compliance problem the IRS is now fully equipped to pursue.

This is no longer about gray areas or technicalities. It’s about a growing mismatch between how taxpayers think crypto taxes work — and how the IRS now expects them to be handled. That gap is where the risk lives, and with the established guidance, the IRS won’t be pulling any punches.

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Elon Musk’s xAI Partners With Kalshi to Bring Grok to Prediction Markets

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Elon Musk’s artificial intelligence startup xAI is partnering with regulated prediction market Kalshi to bring its chatbot Grok into the world of real-money event forecasting, the companies said Thursday.

The collaboration will allow Grok to analyze news, historical data and economic indicators in real time to support users trading on Kalshi’s federally regulated platform. Kalshi traders can place bets on specific outcomes of events like Federal Reserve interest rate decisions, Senate control, or monthly inflation figures — making Grok’s ability to summarize information quickly a potential edge.

“Kalshi and xAI are partnering to bring Grok to prediction markets. Two of the fastest growing companies in America are now on the same team,” xAI said in a post on X.

The deal brings together Musk’s latest AI venture, known for its irreverent chatbot Grok, and Kalshi, the only U.S.-regulated prediction market that offers tradable event contracts. While details of how Grok will be integrated weren’t disclosed, Bloomberg previously reported (and then retracted) in May that both companies are committing “significant engineering resources” to the project.

The announcement also adds complexity to xAI and Musk’s broader prediction market strategy.

Earlier this year, xAI and X named Polymarket — an unregulated crypto-based competitor to Kalshi — as their official prediction market partner. Now, with Kalshi and Polymarket effectively operating in parallel under Musk’s orbit, the market appears to be a testing ground for Grok’s AI capabilities across different regulatory frameworks.

Grok’s most recent version, Grok 4, was unveiled earlier this month, promising major upgrades in reasoning and information retrieval.

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Polkadot’s DOT Bounces After 7% Decline

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Polkadot’s DOT staged a strong recovery after slumping as much as 7%, bouncing from $3.91 to $4.08 amid high trading volumes, according to CoinDesk Research’s technical analysis model.

The model showed that DOT navigated substantial price swings during the 24-hour period from July 23 19:00 to July 24 18:00, oscillating between $3.91 and $4.20 before settling at $4.08.

Earlier this week, the Securities and Exchange Commission (SEC) withdrew its accelerated approval for a Bitwise crypto exchange-traded fund (ETF) that plans to include DOT among its top holdings by market cap.

The bounce in Polkadot came as the wider crypto market also rose, with the broader market gauge, the Coindesk 20, recently up 1.4%.

In recent trading, DOT was 2% lower over 24 hours, trading around $4.09.

Technical Analysis:
  • Overall trading range of $0.28 representing 7% volatility between $4.20 maximum and $3.91 minimum.
  • Critical support level established at $3.96 with high volume confirmation exceeding 4.28 million average.
  • Resistance zone identified at $4.10 level showing price rejection patterns.
  • Volume spike of 73,061 during decline phase indicating institutional selling pressure.
  • Recovery pattern suggests potential continuation toward $4.13 target level.
  • Net decline of 2% from opening despite strong bounce from overnight lows.

Disclaimer: Parts of this article were generated with the assistance from AI tools and reviewed by our editorial team to ensure accuracy and adherence to our standards. For more information, see CoinDesk’s full AI Policy.

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Yuga Labs Bored Ape Yacht Club $9M Win Against Ryder Ripps Overturned, Must Better Prove Trademark Infringement

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The creator of the Bored Ape Yacht Club non-fungible tokens (NFTs) needs to better prove that a «satirical» version of these tokens was meant to mislead would-be buyers, a U.S. appeals court said Wednesday, overturning a lower court ruling and sending the case back to that lower court for a new trial.

The U.S. Court of Appeals for the Ninth Circuit ruled that a District Court finding that Ryder Ripps’ NFT collection harmed Yuga Labs’ trademarked NFTs needs to be reconsidered, though without weighing in on whether there was indeed trademark infringement — only that Yuga needed to do a better job of demonstrating that under the law at a new trial, a court document said.

Ryder Ripps and Jeremy Cahen, the duo behind the RR/BAYC NFT collection, had previously argued that their tokens were meant to be a satirical response to the actual BAYC. Yuga Labs sued in 2022, alleging trademark infringement and cybersquatting.

A partial summary judgement by a district judge found that Yuga does own trademarks to its Bored Ape Yacht Club NFT collection and that Ripps’ RR/BAYC NFT collection did cause confusion as the images did look similar. Ripps appealed the final ruling, which included an over $8 million fine to be paid to Yuga. The appeals court said that while Yuga does have priority on the trademark due to being the first to use «the Bored Ape Yacht Club marks,» it had not proven that Ripps’ NFTs were causing confusion.

Nevertheless, Yuga Labs must return to trial. «Yuga may ultimately prevail on these claims, but to do so it must convince a factfinder at trial,» the filing said.

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