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Whether you're a longtime crypto investor or recently purchased digital assets, here are some key things to know from crypto tax experts. For 2023, there's a "digital assets" question on the front page of Form 1040, along with returns for estates and trusts, partnerships, corporations and S corporations. Andrew Gordon President of Gordon Law Group"Yes-or-no questions are quite powerful," said Andrew Gordon, tax attorney, certified public accountant and president of Gordon Law Group. However, the 2023 digital assets question does not apply to bitcoin futures ETFs or spot bitcoin ETFs, he said. How crypto tax reporting works
Persons: Cryptocurrency, Matt Metras, Andrew Gordon President, Andrew Gordon, Gordon, They're Organizations: IRS, MDM Financial, Gordon Law, Gordon Law Group
But there's a catch with conventional assets: the wash sale rule . Now, tax professionals are flagging a potential wrinkle that may arise: Even though bitcoin itself isn't subject to the wash sale rule, a spot bitcoin ETF very well may be. Property versus security Under federal tax law, the IRS deems cryptocurrency to be property . Managing limitations At its core, that means investors should avoid swapping in and out of the same spot bitcoin ETF within the 61-day limit if they had sold the position. This also raises the question of whether dumping one spot bitcoin ETF for another would be deemed substantially identical.
Persons: Stephen Turanchik, Paul Hastings, Andrew Gordon, Dan Herron, Richard LaFalce, Morgan Lewis, Turanchik Organizations: Internal, Digital, Tax, Force, American Institute of CPAs, IRS, Gordon Law Group, Elemental Wealth, Investors Locations: San Luis Obispo , California
STR | NurPhoto via Getty ImagesAs investors weigh year-end tax moves, there may be a lesser-known savings opportunity for certain cryptocurrency investors, experts say. After the crypto industry lost nearly $1.4 trillion in 2022, many investors leveraged tax loss harvesting, which uses losses to offset profits. But after a rally in 2023, you may consider strategically selling profitable crypto held in brokerage accounts, known as "tax gain harvesting." Investors "really ought to be paying attention" to tax-free opportunities to harvest crypto gains, according to Wheelwright. Still, the tax gain strategy allows you to sell at a gain and pay no tax, whereas "tax loss harvesting defers future tax," Gordon said.
Persons: Tom Wheelwright, Wheelwright, Andrew Gordon, Gordon, That's Organizations: Getty Images, Gordon Law Group, IRS
oatawa | GettyAs the U.S. Department of the Treasury and IRS roll out proposed regulations for crypto tax reporting, experts say it's critical for investors to accurately report and track activity. Stemming from the 2021 federal infrastructure bill, the agencies on Friday unveiled the long-awaited tax reporting proposal for cryptocurrency, non-fungible tokens and other digital assets. It's part of a broader effort to "close the tax gap" and address crypto tax evasion, according to the Treasury. Similar to other tax forms, the regulations would require brokers to begin sending Form 1099-DA to the IRS and investors in January 2026, to report crypto activity from 2025. "But a lot of individuals are looking at six to seven figures, potentially, of crypto activity that they've never reported," he said.
Persons: , there's, Andrew Gordon, Alex Roytenberg, they've Organizations: Getty, U.S . Department of, Treasury, IRS, Gordon Law Group
Here's how to report 2022 crypto losses on your tax return
  + stars: | 2023-03-15 | by ( Kate Dore | Cfp | ) www.cnbc.com   time to read: +3 min
But if you're still recovering from last year's losses, it may be possible to score a tax break on your 2022 return. The crypto market plunged by nearly $1.4 trillion in 2022 after a series of bankruptcies, liquidity issues and the collapse of FTX, one of the biggest crypto exchanges. If you're itching to claim a crypto loss on your taxes, there are a few things to know, experts say. Offset gains with crypto lossesOne of the silver linings of plummeting assets is the chance to leverage tax-loss harvesting, or using losses to offset gains. If your crypto losses exceed other investment gains and $3,000 of regular income, you can use the rest in subsequent years, Greene-Lewis said.
Plus, there's currently no "wash sale rule" for crypto. The rule blocks the tax break if you buy a "substantially identical" asset 30 days before or after the sale. If your crypto losses exceed other investment gains and $3,000 of regular income, you can use the rest in subsequent years, Greene-Lewis said. But it's easy to lose track of carryover losses and miss future opportunities to lower taxes, she warned. If you wind up getting, say, 10% back after claiming a bad debt deduction, that 10% becomes regular income.
The IRS continues to chase U.S. taxpayers who failed to report and pay taxes on cryptocurrency transactions with a new court order allowing a summons for customer records. The agency will issue a so-called "John Doe summons" requiring M.Y. It's not the first IRS summons for crypto records, but it's unusual because the broker seems to be "quite small," signaling the possibility of more to come, said Andrew Gordon, tax attorney, CPA and president of Gordon Law Group in Skokie, Illinois. While the first summons for crypto tax records triggered IRS letters for unreported income and unpaid taxes, the response took a few years, said Matt Metras, an enrolled agent and cryptocurrency tax specialist at MDM Financial Services in Rochester, New York. "I'm curious to see what happens with all this data they're collecting," said Metras, noting that the IRS may try to match it with investors' tax returns.
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